diff --git a/e2e/oauth/sidebar-connection-status.spec.ts b/e2e/oauth/sidebar-connection-status.spec.ts
index d46a0c53b..f8fbfa2e1 100644
--- a/e2e/oauth/sidebar-connection-status.spec.ts
+++ b/e2e/oauth/sidebar-connection-status.spec.ts
@@ -1,7 +1,8 @@
-import { expect, test } from "@playwright/test";
+import { type Page, expect, test } from "@playwright/test";
 import {
   type GoogleConnectionState,
   SIDEBAR_STATUS_LABELS,
+  expectGoogleConnectionStateInStore,
   markUserAsAuthenticated,
   prepareOAuthTestPage,
   setGoogleConnectionState,
@@ -9,21 +10,11 @@ import {
 } from "../utils/oauth-test-utils";
 
 /**
- * E2E tests for sidebar Google Calendar connection status.
+ * E2E tests for Google Calendar connection state (Redux + header status when visible).
  *
- * These tests verify that the sidebar status container correctly reflects the 5 connection
- * states from the server (GoogleConnectionState), plus the client-only "checking"
- * state that appears while metadata is loading.
- *
- * Connection states and their status messages:
- * - NOT_CONNECTED: "Google Calendar not connected. Click to connect."
- * - RECONNECT_REQUIRED: "Google Calendar needs reconnecting. Click to reconnect."
- * - IMPORTING: "Google Calendar is syncing in the background."
- * - HEALTHY: "Google Calendar connected."
- * - ATTENTION: "Google Calendar needs repair. Click to repair."
- * - "checking" (client-only): "Checking Google Calendar status…"
- *
- * The status is rendered in SidebarIconRow with role="status" and managed by useConnectGoogle hook.
+ * HeaderInfoIcon only renders role="status" for warning/error states (reconnect required,
+ * needs repair). Other states are reflected in Redux only; command palette still exposes
+ * connect/repair actions.
  *
  * NOTE: These tests are skipped on mobile because the MobileGate component
  * blocks the entire app on mobile viewports.
@@ -35,10 +26,8 @@ test.describe("Sidebar Connection Status", () => {
   // Run tests serially to avoid state interference
   test.describe.configure({ mode: "serial" });
 
-  // Helper to get the sidebar status container
-  // Filter: has aria-label (excludes DndLiveRegion), no aria-busy (excludes overlay)
-  const getSidebarStatus = (page: import("@playwright/test").Page) =>
-    page.locator('#sidebar [role="status"][aria-label]:not([aria-busy])');
+  const getHeaderGoogleStatus = (page: Page) =>
+    page.locator("#cal").getByRole("status", { name: /Google Calendar/i });
 
   test.beforeEach(async ({ page }) => {
     await prepareOAuthTestPage(page);
@@ -50,35 +39,24 @@ test.describe("Sidebar Connection Status", () => {
     await setGoogleConnectionState(page, "NOT_CONNECTED");
   });
 
-  test("shows NOT_CONNECTED status", async ({ page }) => {
-    // State already set in beforeEach - just verify it
-
-    const status = getSidebarStatus(page);
-    await expect(status).toHaveAttribute(
-      "aria-label",
-      SIDEBAR_STATUS_LABELS.notConnected,
-    );
+  test("stores NOT_CONNECTED in Redux (header icon hidden for muted state)", async ({
+    page,
+  }) => {
+    await expectGoogleConnectionStateInStore(page, "NOT_CONNECTED");
   });
 
-  test("shows checking status when metadata is loading", async ({ page }) => {
-    // The "checking" state requires:
-    // 1. userMetadataStatus === "loading"
-    // 2. hasUserEverAuthenticated() returns true (localStorage flag)
-    //
-    // Set the localStorage flag first, then force loading state.
+  test("checking path: authenticated user with metadata loading", async ({
+    page,
+  }) => {
     await markUserAsAuthenticated(page);
 
-    // Force the loading state by dispatching both clear and setLoading
     await page.evaluate(() => {
       const store = window.__COMPASS_E2E_STORE__;
       if (!store) return;
-      // Clear any existing metadata
       store.dispatch({ type: "userMetadata/clear" });
-      // Set to loading state
       store.dispatch({ type: "userMetadata/setLoading" });
     });
 
-    // Wait for state to be in loading
     await page.waitForFunction(
       () =>
         window.__COMPASS_E2E_STORE__?.getState()?.userMetadata?.status ===
@@ -86,12 +64,8 @@ test.describe("Sidebar Connection Status", () => {
       { timeout: 5000 },
     );
 
-    // Wait for status container to show "checking" state via aria-label
-    const status = getSidebarStatus(page);
-    await expect(status).toHaveAttribute(
-      "aria-label",
-      /Checking Google Calendar/i,
-    );
+    // "Checking" does not render HeaderInfoIcon (muted / no warning-error icon).
+    await expect(getHeaderGoogleStatus(page)).toHaveCount(0);
   });
 
   test("shows IMPORTING status", async ({ page }) => {
@@ -118,11 +92,6 @@ test.describe("Sidebar Connection Status - State Transitions", () => {
   // Run tests serially to avoid state interference
   test.describe.configure({ mode: "serial" });
 
-  // Helper to get the sidebar status container
-  // Filter: has aria-label (excludes DndLiveRegion), no aria-busy (excludes overlay)
-  const getSidebarStatus = (page: import("@playwright/test").Page) =>
-    page.locator('#sidebar [role="status"][aria-label]:not([aria-busy])');
-
   test.beforeEach(async ({ page }) => {
     await prepareOAuthTestPage(page);
     await page.goto("/week");
@@ -133,23 +102,20 @@ test.describe("Sidebar Connection Status - State Transitions", () => {
     await setGoogleConnectionState(page, "NOT_CONNECTED");
   });
 
-  test("transitions from NOT_CONNECTED to HEALTHY correctly", async ({
+  test("transitions from RECONNECT_REQUIRED to ATTENTION correctly", async ({
     page,
   }) => {
-    const status = getSidebarStatus(page);
-
-    // State already set to NOT_CONNECTED in beforeEach - just verify it
-    await expect(status).toHaveAttribute(
-      "aria-label",
-      SIDEBAR_STATUS_LABELS.notConnected,
-    );
+    await setGoogleConnectionState(page, "RECONNECT_REQUIRED");
+    await expect(
+      page.getByRole("status", {
+        name: SIDEBAR_STATUS_LABELS.reconnectRequired,
+      }),
+    ).toBeVisible();
 
-    // Transition to HEALTHY (simulating successful OAuth flow)
-    await setGoogleConnectionState(page, "HEALTHY");
-    await expect(status).toHaveAttribute(
-      "aria-label",
-      SIDEBAR_STATUS_LABELS.connected,
-    );
+    await setGoogleConnectionState(page, "ATTENTION");
+    await expect(
+      page.getByRole("status", { name: SIDEBAR_STATUS_LABELS.needsRepair }),
+    ).toBeVisible();
   });
 
   test("cycles through connection states without visual glitches", async ({
@@ -165,14 +131,12 @@ test.describe("Sidebar Connection Status - State Transitions", () => {
 
     for (const state of states) {
       await setGoogleConnectionState(page, state);
-      // setGoogleConnectionState now waits for aria-label, no timeout needed
     }
 
-    // Should end on RECONNECT_REQUIRED
-    const status = getSidebarStatus(page);
-    await expect(status).toHaveAttribute(
-      "aria-label",
-      SIDEBAR_STATUS_LABELS.reconnectRequired,
-    );
+    await expect(
+      page.getByRole("status", {
+        name: SIDEBAR_STATUS_LABELS.reconnectRequired,
+      }),
+    ).toBeVisible();
   });
 });
diff --git a/e2e/utils/oauth-test-utils.ts b/e2e/utils/oauth-test-utils.ts
index 6cd0be68d..edd055e20 100644
--- a/e2e/utils/oauth-test-utils.ts
+++ b/e2e/utils/oauth-test-utils.ts
@@ -1,4 +1,4 @@
-import { Page, expect } from "@playwright/test";
+import { type Page, expect } from "@playwright/test";
 import "./compass-window";
 
 /**
@@ -200,13 +200,20 @@ const CONNECTION_STATE_TO_LABEL: Record<GoogleConnectionState, RegExp> = {
   ATTENTION: /needs repair/i,
 };
 
-const SIDEBAR_STATUS_SELECTOR =
-  "#sidebar [role='status'][aria-label]:not([aria-busy])";
+/**
+ * HeaderInfoIcon only renders role="status" for warning/error connection states
+ * (see HeaderInfoIcon.tsx). Muted / checking / importing-without-background-import
+ * do not expose this region.
+ */
+const GOOGLE_HEADER_STATUS_VISIBLE_STATES: GoogleConnectionState[] = [
+  "RECONNECT_REQUIRED",
+  "ATTENTION",
+];
 
 /**
  * Set the Google connection state via Redux userMetadata slice.
- * Dispatches to the store and waits for the sidebar aria-label to update.
- * waitForAppReady in beforeEach guarantees the store is ready before this runs.
+ * Dispatches to the store, waits for Redux to match, then asserts the header
+ * status region when the UI shows it (reconnect required / needs repair).
  */
 export const setGoogleConnectionState = async (
   page: Page,
@@ -221,9 +228,37 @@ export const setGoogleConnectionState = async (
     });
   }, state);
 
-  await expect(page.locator(SIDEBAR_STATUS_SELECTOR)).toHaveAttribute(
-    "aria-label",
-    CONNECTION_STATE_TO_LABEL[state],
+  await page.waitForFunction(
+    (expected) => {
+      const cs =
+        window.__COMPASS_E2E_STORE__?.getState()?.userMetadata?.current?.google
+          ?.connectionState;
+      return cs === expected;
+    },
+    state,
+    { timeout: 5000 },
+  );
+
+  if (GOOGLE_HEADER_STATUS_VISIBLE_STATES.includes(state)) {
+    await expect(
+      page.getByRole("status", { name: CONNECTION_STATE_TO_LABEL[state] }),
+    ).toBeVisible();
+  }
+};
+
+export const expectGoogleConnectionStateInStore = async (
+  page: Page,
+  state: GoogleConnectionState,
+) => {
+  await page.waitForFunction(
+    (expected) => {
+      const cs =
+        window.__COMPASS_E2E_STORE__?.getState()?.userMetadata?.current?.google
+          ?.connectionState;
+      return cs === expected;
+    },
+    state,
+    { timeout: 5000 },
   );
 };
 
diff --git a/eslint.config.mjs b/eslint.config.mjs
index c6881b9bd..628e3b637 100644
--- a/eslint.config.mjs
+++ b/eslint.config.mjs
@@ -111,6 +111,15 @@ export default [
       "jest/unbound-method": "error",
     },
   },
+  {
+    files: ["e2e/**/*.ts"],
+    rules: {
+      // Playwright e2e is not React Testing Library; page.getByRole is correct.
+      "testing-library/prefer-screen-queries": "off",
+      "@typescript-eslint/no-unsafe-assignment": "off",
+      "@typescript-eslint/no-unsafe-member-access": "off",
+    },
+  },
   // Warn on console.log in packages/web to avoid leaking secure info
   {
     files: ["packages/web/**/*.{ts,tsx}"],
diff --git a/packages/backend/src/sync/controllers/sync.controller.test.ts b/packages/backend/src/sync/controllers/sync.controller.test.ts
index cd0d1a069..f8aa389c2 100644
--- a/packages/backend/src/sync/controllers/sync.controller.test.ts
+++ b/packages/backend/src/sync/controllers/sync.controller.test.ts
@@ -42,9 +42,10 @@ describe("SyncController", () => {
   const baseDriver = new BaseDriver();
   const syncDriver = new SyncControllerDriver(baseDriver);
   const importTimeoutMs = 7_000;
+  type ImportOperation = "INCREMENTAL" | "REPAIR";
 
   interface ImportSummary {
-    operation: "REPAIR";
+    operation: ImportOperation;
     status: "COMPLETED";
     eventsCount: number;
     calendarsCount: number;
@@ -52,10 +53,11 @@ describe("SyncController", () => {
 
   function parseImportResult(
     result: ImportGCalEndPayload | undefined,
+    operation: ImportOperation = "INCREMENTAL",
   ): ImportSummary {
     expect(result).toEqual(
       expect.objectContaining({
-        operation: "REPAIR",
+        operation,
         status: "COMPLETED",
         eventsCount: expect.any(Number) as number,
         calendarsCount: expect.any(Number) as number,
@@ -607,7 +609,7 @@ describe("SyncController", () => {
         const result = (await importEndPromise) as ImportGCalEndPayload;
         stream.close();
 
-        const parsed = parseImportResult(result);
+        const parsed = parseImportResult(result, "REPAIR");
 
         expect(parsed).toHaveProperty("eventsCount");
         expect(parsed).toHaveProperty("calendarsCount");
@@ -643,7 +645,7 @@ describe("SyncController", () => {
         stream.close();
 
         expect(failReason).toEqual({
-          operation: "REPAIR",
+          operation: "INCREMENTAL",
           status: "IGNORED",
           message: `User ${userId} gcal import is in progress or completed, ignoring this request`,
         });
@@ -683,7 +685,7 @@ describe("SyncController", () => {
         stream.close();
 
         expect(failReason).toEqual({
-          operation: "REPAIR",
+          operation: "INCREMENTAL",
           status: "IGNORED",
           message: `User ${userId} gcal import is in progress or completed, ignoring this request`,
         });
diff --git a/packages/backend/src/sync/services/sync.service.test.ts b/packages/backend/src/sync/services/sync.service.test.ts
index abf005719..a43ac30fb 100644
--- a/packages/backend/src/sync/services/sync.service.test.ts
+++ b/packages/backend/src/sync/services/sync.service.test.ts
@@ -447,6 +447,7 @@ describe("SyncService", () => {
     it("restarts the import workflow and completes successfully", async () => {
       const { user } = await UtilDriver.setupTestUser();
       const userId = user._id.toString();
+      const importEndSpy = jest.spyOn(sseServer, "handleImportGCalEnd");
 
       await userMetadataService.updateUserMetadata({
         userId,
@@ -462,11 +463,19 @@ describe("SyncService", () => {
         calendarService.getByUser.bind(calendarService);
       const calendars = await listCalendarsForUser(userId);
       expect(calendars.length).toBeGreaterThan(0);
+      expect(importEndSpy).toHaveBeenCalledWith(
+        userId,
+        expect.objectContaining({
+          operation: "INCREMENTAL",
+          status: "COMPLETED",
+        }),
+      );
     });
 
     it("skips restart when import is completed and not forced", async () => {
       const { user } = await UtilDriver.setupTestUser();
       const userId = user._id.toString();
+      const importEndSpy = jest.spyOn(sseServer, "handleImportGCalEnd");
 
       await userMetadataService.updateUserMetadata({
         userId,
@@ -483,6 +492,11 @@ describe("SyncService", () => {
 
       const metadata = await userMetadataService.fetchUserMetadata(userId);
       expect(metadata.sync?.importGCal).toBe("COMPLETED");
+      expect(importEndSpy).toHaveBeenCalledWith(userId, {
+        operation: "INCREMENTAL",
+        status: "IGNORED",
+        message: `User ${userId} gcal import is in progress or completed, ignoring this request`,
+      });
 
       stopSpy.mockRestore();
       startSpy.mockRestore();
@@ -516,6 +530,64 @@ describe("SyncService", () => {
       startSpy.mockRestore();
     });
 
+    it("ignores a duplicate restart while the first full sync is still starting", async () => {
+      const { user } = await UtilDriver.setupTestUser();
+      const userId = user._id.toString();
+      const importEndSpy = jest.spyOn(sseServer, "handleImportGCalEnd");
+      let resolveFetchMetadata: (() => void) | undefined;
+      const fetchMetadataDeferred = new Promise<void>((resolve) => {
+        resolveFetchMetadata = resolve;
+      });
+      let fetchMetadataCallCount = 0;
+
+      await userMetadataService.updateUserMetadata({
+        userId,
+        data: { sync: { importGCal: "RESTART" } },
+      });
+
+      const fetchMetadataSpy = jest
+        .spyOn(userService, "fetchUserMetadata")
+        .mockImplementation(async (targetUserId) => {
+          fetchMetadataCallCount += 1;
+
+          if (fetchMetadataCallCount === 1) {
+            await fetchMetadataDeferred;
+          }
+
+          return userMetadataService.fetchUserMetadata(targetUserId);
+        });
+      const startSpy = jest
+        .spyOn(syncService, "startGoogleCalendarSync")
+        .mockResolvedValue({ eventsCount: 0, calendarsCount: 0 });
+      const stopSpy = jest
+        .spyOn(userService, "stopGoogleCalendarSync")
+        .mockResolvedValue();
+
+      const firstRestart = syncService.restartGoogleCalendarSync(userId, {
+        force: true,
+      });
+      await Promise.resolve();
+
+      const secondRestart = syncService.restartGoogleCalendarSync(userId, {
+        force: true,
+      });
+
+      resolveFetchMetadata?.();
+
+      await Promise.all([firstRestart, secondRestart]);
+
+      expect(startSpy).toHaveBeenCalledTimes(1);
+      expect(importEndSpy).toHaveBeenCalledWith(userId, {
+        operation: "REPAIR",
+        status: "IGNORED",
+        message: `User ${userId} gcal import is in progress or completed, ignoring this request`,
+      });
+
+      fetchMetadataSpy.mockRestore();
+      startSpy.mockRestore();
+      stopSpy.mockRestore();
+    });
+
     it("cleans up partial watch state when restart fails", async () => {
       const { user } = await UtilDriver.setupTestUser();
       const userId = user._id.toString();
diff --git a/packages/backend/src/sync/services/sync.service.ts b/packages/backend/src/sync/services/sync.service.ts
index b0f5a313c..ede52fee0 100644
--- a/packages/backend/src/sync/services/sync.service.ts
+++ b/packages/backend/src/sync/services/sync.service.ts
@@ -59,6 +59,8 @@ import userMetadataService from "@backend/user/services/user-metadata.service";
 const logger = Logger("app:sync.service");
 
 class SyncService {
+  private activeFullSyncRestarts = new Set<string>();
+
   deleteAllByGcalId = async (gCalendarId: string, session?: ClientSession) => {
     const delRes = await mongoService.sync.deleteMany(
       { "google.events.gCalendarId": gCalendarId },
@@ -530,6 +532,19 @@ class SyncService {
     const { default: userService } =
       await import("@backend/user/services/user.service");
     const isForce = options.force === true;
+    const operation = isForce ? "REPAIR" : "INCREMENTAL";
+    const ignoreMessage = `User ${userId} gcal import is in progress or completed, ignoring this request`;
+
+    if (this.activeFullSyncRestarts.has(userId)) {
+      sseServer.handleImportGCalEnd(userId, {
+        operation,
+        status: "IGNORED",
+        message: ignoreMessage,
+      });
+      return;
+    }
+
+    this.activeFullSyncRestarts.add(userId);
 
     try {
       const userMeta = await userService.fetchUserMetadata(userId);
@@ -539,9 +554,9 @@ class SyncService {
 
       if (!proceed) {
         sseServer.handleImportGCalEnd(userId, {
-          operation: "REPAIR",
+          operation,
           status: "IGNORED",
-          message: `User ${userId} gcal import is in progress or completed, ignoring this request`,
+          message: ignoreMessage,
         });
 
         return;
@@ -572,7 +587,7 @@ class SyncService {
       });
 
       sseServer.handleImportGCalEnd(userId, {
-        operation: "REPAIR",
+        operation,
         status: "COMPLETED",
         ...importResults,
       });
@@ -605,10 +620,12 @@ class SyncService {
       logger.error(`Re-sync failed for user: ${userId}`, err);
 
       sseServer.handleImportGCalEnd(userId, {
-        operation: "REPAIR",
+        operation,
         status: "ERRORED",
         message: getGoogleRepairErrorMessage(err),
       });
+    } finally {
+      this.activeFullSyncRestarts.delete(userId);
     }
   };
 
diff --git a/packages/backend/src/user/services/user-metadata.service.test.ts b/packages/backend/src/user/services/user-metadata.service.test.ts
index ddb85f23e..bd5b08bb5 100644
--- a/packages/backend/src/user/services/user-metadata.service.test.ts
+++ b/packages/backend/src/user/services/user-metadata.service.test.ts
@@ -150,5 +150,19 @@ describe("UserMetadataService", () => {
 
       restartSpy.mockRestore();
     });
+
+    it("returns ATTENTION when a restart is pending", async () => {
+      const user = await UserDriver.createUser();
+      const userId = user._id.toString();
+
+      await driver.updateUserMetadata({
+        userId,
+        data: { sync: { importGCal: "RESTART" } },
+      });
+
+      const metadata = await driver.fetchUserMetadata(userId);
+
+      expect(metadata.google?.connectionState).toBe("ATTENTION");
+    });
   });
 });
diff --git a/packages/backend/src/user/services/user-metadata.service.ts b/packages/backend/src/user/services/user-metadata.service.ts
index fafcebafa..ef915f960 100644
--- a/packages/backend/src/user/services/user-metadata.service.ts
+++ b/packages/backend/src/user/services/user-metadata.service.ts
@@ -94,10 +94,14 @@ class UserMetadataService {
     }
 
     const importStatus = storedMetadata.sync?.importGCal;
-    if (importStatus === "IMPORTING" || importStatus === "RESTART") {
+    if (importStatus === "IMPORTING") {
       return { connectionState: "IMPORTING" };
     }
 
+    if (importStatus === "RESTART") {
+      return { connectionState: "ATTENTION" };
+    }
+
     const isHealthy = await this.isGoogleSyncHealthy(userId);
     if (isHealthy) {
       return { connectionState: "HEALTHY" };
diff --git a/packages/web/src/__tests__/__mocks__/mock.setup.ts b/packages/web/src/__tests__/__mocks__/mock.setup.ts
index ef2c5c059..bb3c8a68b 100644
--- a/packages/web/src/__tests__/__mocks__/mock.setup.ts
+++ b/packages/web/src/__tests__/__mocks__/mock.setup.ts
@@ -57,7 +57,7 @@ export function mockLinuxUserAgent() {
 }
 
 export function mockUseGoogleLogin() {
-  mockModule("@web/auth/hooks/google/useGoogleLogin/useGoogleLogin", () => ({
+  mockModule("@web/auth/google/hooks/useGoogleLogin/useGoogleLogin", () => ({
     useGoogleLogin: jest.fn().mockReturnValue({
       login: jest.fn(),
       loading: false,
diff --git a/packages/web/src/__tests__/__mocks__/state/state.weekEvents.ts b/packages/web/src/__tests__/__mocks__/state/state.weekEvents.ts
index 514c90286..f20086c15 100644
--- a/packages/web/src/__tests__/__mocks__/state/state.weekEvents.ts
+++ b/packages/web/src/__tests__/__mocks__/state/state.weekEvents.ts
@@ -84,12 +84,6 @@ export const preloadedState: InitialReduxState = {
     status: "idle",
   },
   sync: {
-    importGCal: {
-      isRepairing: false,
-      importResults: null,
-      pendingLocalEventsSynced: null,
-      importError: null,
-    },
     importLatest: {
       isFetchNeeded: false,
       reason: null,
diff --git a/packages/web/src/__tests__/utils/state/store.test.util.ts b/packages/web/src/__tests__/utils/state/store.test.util.ts
index 6c6a12488..c92260dbd 100644
--- a/packages/web/src/__tests__/utils/state/store.test.util.ts
+++ b/packages/web/src/__tests__/utils/state/store.test.util.ts
@@ -122,12 +122,6 @@ export const createInitialState = (
       status: "idle",
     },
     sync: {
-      importGCal: {
-        isRepairing: false,
-        importResults: null,
-        pendingLocalEventsSynced: null,
-        importError: null,
-      },
       importLatest: {
         isFetchNeeded: false,
         reason: null,
diff --git a/packages/web/src/auth/hooks/compass/useCompleteAuthentication.test.ts b/packages/web/src/auth/compass/hooks/useCompleteAuthentication.test.ts
similarity index 65%
rename from packages/web/src/auth/hooks/compass/useCompleteAuthentication.test.ts
rename to packages/web/src/auth/compass/hooks/useCompleteAuthentication.test.ts
index 942b70bf3..c0336355f 100644
--- a/packages/web/src/auth/hooks/compass/useCompleteAuthentication.test.ts
+++ b/packages/web/src/auth/compass/hooks/useCompleteAuthentication.test.ts
@@ -1,26 +1,29 @@
 import { renderHook } from "@testing-library/react";
-import type * as GoogleAuthUtil from "@web/auth/google/google.auth.util";
-import { syncPendingLocalEvents } from "@web/auth/google/google.auth.util";
-import { useSession } from "@web/auth/hooks/session/useSession";
-import { refreshUserMetadata } from "@web/auth/session/user-metadata.util";
-import { markUserAsAuthenticated } from "@web/auth/state/auth.state.util";
-import { importGCalSlice } from "@web/ducks/events/slices/sync.slice";
+import { useSession } from "@web/auth/compass/session/useSession";
+import {
+  clearAnonymousCalendarChangeSignUpPrompt,
+  markUserAsAuthenticated,
+} from "@web/auth/compass/state/auth.state.util";
+import { refreshUserMetadata } from "@web/auth/compass/user/util/user-metadata.util";
+import type * as GoogleAuthUtil from "@web/auth/google/util/google.auth.util";
+import { syncPendingLocalEvents } from "@web/auth/google/util/google.auth.util";
 import { useAppDispatch } from "@web/store/store.hooks";
 import { useCompleteAuthentication } from "./useCompleteAuthentication";
 
-jest.mock("@web/auth/google/google.auth.util", () => ({
+jest.mock("@web/auth/google/util/google.auth.util", () => ({
   ...jest.requireActual<typeof GoogleAuthUtil>(
-    "@web/auth/google/google.auth.util",
+    "@web/auth/google/util/google.auth.util",
   ),
   syncPendingLocalEvents: jest.fn(),
 }));
-jest.mock("@web/auth/hooks/session/useSession", () => ({
+jest.mock("@web/auth/compass/session/useSession", () => ({
   useSession: jest.fn(),
 }));
-jest.mock("@web/auth/session/user-metadata.util", () => ({
+jest.mock("@web/auth/compass/user/util/user-metadata.util", () => ({
   refreshUserMetadata: jest.fn(),
 }));
-jest.mock("@web/auth/state/auth.state.util", () => ({
+jest.mock("@web/auth/compass/state/auth.state.util", () => ({
+  clearAnonymousCalendarChangeSignUpPrompt: jest.fn(),
   markUserAsAuthenticated: jest.fn(),
 }));
 jest.mock("@web/store/store.hooks", () => ({
@@ -37,6 +40,10 @@ const mockMarkUserAsAuthenticated =
   markUserAsAuthenticated as jest.MockedFunction<
     typeof markUserAsAuthenticated
   >;
+const mockClearAnonymousCalendarChangeSignUpPrompt =
+  clearAnonymousCalendarChangeSignUpPrompt as jest.MockedFunction<
+    typeof clearAnonymousCalendarChangeSignUpPrompt
+  >;
 const mockUseAppDispatch = jest.mocked(useAppDispatch);
 
 describe("useCompleteAuthentication", () => {
@@ -59,6 +66,7 @@ describe("useCompleteAuthentication", () => {
 
     await result.current({ email: "test@example.com" });
 
+    expect(mockClearAnonymousCalendarChangeSignUpPrompt).toHaveBeenCalled();
     expect(mockMarkUserAsAuthenticated).toHaveBeenCalledWith(
       "test@example.com",
     );
@@ -73,19 +81,11 @@ describe("useCompleteAuthentication", () => {
   });
 
   it("records synced local events count", async () => {
-    mockSyncPendingLocalEvents.mockImplementation((dispatch) => {
-      dispatch(importGCalSlice.actions.setLocalEventsSynced(5));
-      return Promise.resolve(true);
-    });
+    mockSyncPendingLocalEvents.mockResolvedValue(true);
     const { result } = renderHook(() => useCompleteAuthentication());
 
     await result.current({ email: "test@example.com" });
 
-    expect(mockDispatch).toHaveBeenCalledWith(
-      expect.objectContaining({
-        type: "async/importGCal/setLocalEventsSynced",
-        payload: 5,
-      }),
-    );
+    expect(mockSyncPendingLocalEvents).toHaveBeenCalledTimes(1);
   });
 });
diff --git a/packages/web/src/auth/hooks/compass/useCompleteAuthentication.ts b/packages/web/src/auth/compass/hooks/useCompleteAuthentication.ts
similarity index 57%
rename from packages/web/src/auth/hooks/compass/useCompleteAuthentication.ts
rename to packages/web/src/auth/compass/hooks/useCompleteAuthentication.ts
index 7d164e82d..bbdaa37df 100644
--- a/packages/web/src/auth/hooks/compass/useCompleteAuthentication.ts
+++ b/packages/web/src/auth/compass/hooks/useCompleteAuthentication.ts
@@ -1,7 +1,10 @@
-import { syncPendingLocalEvents } from "@web/auth/google/google.auth.util";
-import { useSession } from "@web/auth/hooks/session/useSession";
-import { refreshUserMetadata } from "@web/auth/session/user-metadata.util";
-import { markUserAsAuthenticated } from "@web/auth/state/auth.state.util";
+import { useSession } from "@web/auth/compass/session/useSession";
+import {
+  clearAnonymousCalendarChangeSignUpPrompt,
+  markUserAsAuthenticated,
+} from "@web/auth/compass/state/auth.state.util";
+import { refreshUserMetadata } from "@web/auth/compass/user/util/user-metadata.util";
+import { syncPendingLocalEvents } from "@web/auth/google/util/google.auth.util";
 import { authSuccess } from "@web/ducks/auth/slices/auth.slice";
 import { triggerFetch } from "@web/ducks/events/slices/sync.slice";
 import { useAppDispatch } from "@web/store/store.hooks";
@@ -17,13 +20,14 @@ export function useCompleteAuthentication() {
     email?: string;
     onComplete?: () => void;
   }) => {
+    clearAnonymousCalendarChangeSignUpPrompt();
     markUserAsAuthenticated(email);
     setAuthenticated(true);
     dispatch(authSuccess());
 
     void refreshUserMetadata();
 
-    await syncPendingLocalEvents(dispatch);
+    await syncPendingLocalEvents();
 
     dispatch(triggerFetch());
     onComplete?.();
diff --git a/packages/web/src/auth/schemas/auth.schemas.test.ts b/packages/web/src/auth/compass/schemas/auth.schemas.test.ts
similarity index 100%
rename from packages/web/src/auth/schemas/auth.schemas.test.ts
rename to packages/web/src/auth/compass/schemas/auth.schemas.test.ts
diff --git a/packages/web/src/auth/schemas/auth.schemas.ts b/packages/web/src/auth/compass/schemas/auth.schemas.ts
similarity index 100%
rename from packages/web/src/auth/schemas/auth.schemas.ts
rename to packages/web/src/auth/compass/schemas/auth.schemas.ts
diff --git a/packages/web/src/auth/session/SessionProvider.test.tsx b/packages/web/src/auth/compass/session/SessionProvider.test.tsx
similarity index 88%
rename from packages/web/src/auth/session/SessionProvider.test.tsx
rename to packages/web/src/auth/compass/session/SessionProvider.test.tsx
index e8dd65e89..72985ef1f 100644
--- a/packages/web/src/auth/session/SessionProvider.test.tsx
+++ b/packages/web/src/auth/compass/session/SessionProvider.test.tsx
@@ -2,7 +2,6 @@ import { act } from "react";
 import { waitFor } from "@testing-library/react";
 import { authSlice } from "@web/ducks/auth/slices/auth.slice";
 import { userMetadataSlice } from "@web/ducks/auth/slices/user-metadata.slice";
-import { importGCalSlice } from "@web/ducks/events/slices/sync.slice";
 
 describe("SessionProvider sessionInit", () => {
   beforeEach(() => {
@@ -18,7 +17,7 @@ describe("SessionProvider sessionInit", () => {
     const markUserAsAuthenticated = jest.fn();
     const getLastKnownEmail = jest.fn().mockReturnValue("test@example.com");
 
-    jest.doMock("@web/auth/session/user-metadata.util", () => ({
+    jest.doMock("@web/auth/compass/user/util/user-metadata.util", () => ({
       refreshUserMetadata,
     }));
     jest.doMock("@web/sse/provider/SSEProvider", () => ({
@@ -31,7 +30,7 @@ describe("SessionProvider sessionInit", () => {
         dispatch,
       },
     }));
-    jest.doMock("@web/auth/state/auth.state.util", () => ({
+    jest.doMock("@web/auth/compass/state/auth.state.util", () => ({
       getLastKnownEmail,
       markUserAsAuthenticated,
     }));
@@ -63,7 +62,7 @@ describe("SessionProvider sessionInit", () => {
     const markUserAsAuthenticated = jest.fn();
     const getLastKnownEmail = jest.fn().mockReturnValue("test@example.com");
 
-    jest.doMock("@web/auth/session/user-metadata.util", () => ({
+    jest.doMock("@web/auth/compass/user/util/user-metadata.util", () => ({
       refreshUserMetadata,
     }));
     jest.doMock("@web/sse/provider/SSEProvider", () => ({
@@ -76,7 +75,7 @@ describe("SessionProvider sessionInit", () => {
         dispatch,
       },
     }));
-    jest.doMock("@web/auth/state/auth.state.util", () => ({
+    jest.doMock("@web/auth/compass/state/auth.state.util", () => ({
       getLastKnownEmail,
       markUserAsAuthenticated,
     }));
@@ -104,9 +103,6 @@ describe("SessionProvider sessionInit", () => {
       session.emit("SIGN_OUT", { action: "SIGN_OUT" } as never);
 
       expect(dispatch).toHaveBeenCalledWith(authSlice.actions.resetAuth());
-      expect(dispatch).toHaveBeenCalledWith(
-        importGCalSlice.actions.clearImportResults(undefined),
-      );
       expect(dispatch).toHaveBeenCalledWith(
         userMetadataSlice.actions.clear(undefined),
       );
diff --git a/packages/web/src/auth/session/SessionProvider.tsx b/packages/web/src/auth/compass/session/SessionProvider.tsx
similarity index 92%
rename from packages/web/src/auth/session/SessionProvider.tsx
rename to packages/web/src/auth/compass/session/SessionProvider.tsx
index 33e6020de..a538da353 100644
--- a/packages/web/src/auth/session/SessionProvider.tsx
+++ b/packages/web/src/auth/compass/session/SessionProvider.tsx
@@ -19,17 +19,17 @@ import { APP_NAME } from "@core/constants/core.constants";
 import {
   getLastKnownEmail,
   markUserAsAuthenticated,
-} from "@web/auth/state/auth.state.util";
+} from "@web/auth/compass/state/auth.state.util";
 import { session } from "@web/common/classes/Session";
 import { ENV_WEB } from "@web/common/constants/env.constants";
 import { ROOT_ROUTES } from "@web/common/constants/routes";
 import { authSlice } from "@web/ducks/auth/slices/auth.slice";
 import { userMetadataSlice } from "@web/ducks/auth/slices/user-metadata.slice";
-import { importGCalSlice } from "@web/ducks/events/slices/sync.slice";
 import * as sse from "@web/sse/provider/SSEProvider";
 import { store } from "@web/store";
+import { clearGoogleSyncIndicatorOverride } from "../../google/state/google.sync.state";
+import { refreshUserMetadata } from "../user/util/user-metadata.util";
 import { type CompassSession } from "./session.types";
-import { refreshUserMetadata } from "./user-metadata.util";
 
 SuperTokens.init({
   appInfo: {
@@ -42,7 +42,7 @@ SuperTokens.init({
     EmailPassword.init(),
     EmailVerification.init(),
     Session.init({
-      postAPIHook: async (context) => {
+      postAPIHook: (context) => {
         session.emit(context.action, context);
       },
       onHandleEvent: (event) => {
@@ -69,8 +69,8 @@ const handleSessionExists = () => {
 
 const handleSessionMissing = () => {
   store.dispatch(authSlice.actions.resetAuth());
-  store.dispatch(importGCalSlice.actions.clearImportResults(undefined));
   store.dispatch(userMetadataSlice.actions.clear(undefined));
+  clearGoogleSyncIndicatorOverride();
 };
 
 async function checkIfSessionExists(): Promise<boolean> {
@@ -108,11 +108,11 @@ async function checkIfSessionExists(): Promise<boolean> {
 }
 
 export function sessionInit() {
-  checkIfSessionExists();
+  void checkIfSessionExists();
 
   // No need to unsubscribe as this runs for the lifetime of the app
   session.events.pipe(distinctUntilKeyChanged("action")).subscribe((e) => {
-    checkIfSessionExists();
+    void checkIfSessionExists();
 
     switch (e.action) {
       case "REFRESH_SESSION":
@@ -132,7 +132,7 @@ export function sessionInit() {
   });
 }
 
-export function SessionProvider({ children }: PropsWithChildren<{}>) {
+export function SessionProvider({ children }: PropsWithChildren<object>) {
   const [authenticated, setAuthenticated] = useState(authenticated$.value);
 
   useEffect(() => {
diff --git a/packages/web/src/auth/session/session.types.ts b/packages/web/src/auth/compass/session/session.types.ts
similarity index 100%
rename from packages/web/src/auth/session/session.types.ts
rename to packages/web/src/auth/compass/session/session.types.ts
diff --git a/packages/web/src/auth/session/session.util.test.ts b/packages/web/src/auth/compass/session/session.util.test.ts
similarity index 100%
rename from packages/web/src/auth/session/session.util.test.ts
rename to packages/web/src/auth/compass/session/session.util.test.ts
diff --git a/packages/web/src/auth/session/session.util.ts b/packages/web/src/auth/compass/session/session.util.ts
similarity index 100%
rename from packages/web/src/auth/session/session.util.ts
rename to packages/web/src/auth/compass/session/session.util.ts
diff --git a/packages/web/src/auth/hooks/session/useSession.ts b/packages/web/src/auth/compass/session/useSession.ts
similarity index 56%
rename from packages/web/src/auth/hooks/session/useSession.ts
rename to packages/web/src/auth/compass/session/useSession.ts
index 1b971879e..972f004f7 100644
--- a/packages/web/src/auth/hooks/session/useSession.ts
+++ b/packages/web/src/auth/compass/session/useSession.ts
@@ -1,4 +1,4 @@
 import { useContext } from "react";
-import { SessionContext } from "@web/auth/session/SessionProvider";
+import { SessionContext } from "@web/auth/compass/session/SessionProvider";
 
 export const useSession = () => useContext(SessionContext);
diff --git a/packages/web/src/auth/state/auth.state.util.test.ts b/packages/web/src/auth/compass/state/auth.state.util.test.ts
similarity index 79%
rename from packages/web/src/auth/state/auth.state.util.test.ts
rename to packages/web/src/auth/compass/state/auth.state.util.test.ts
index 18917869b..405364bbf 100644
--- a/packages/web/src/auth/state/auth.state.util.test.ts
+++ b/packages/web/src/auth/compass/state/auth.state.util.test.ts
@@ -4,13 +4,17 @@ import {
   clearGoogleRevokedState,
   isGoogleRevoked,
   markGoogleAsRevoked,
-} from "../google/google.auth.state";
+} from "../../google/state/google.auth.state";
 import {
+  clearAnonymousCalendarChangeSignUpPrompt,
   clearAuthenticationState,
   getAuthState,
   getLastKnownEmail,
   hasUserEverAuthenticated,
+  markAnonymousCalendarChangeForSignUpPrompt,
   markUserAsAuthenticated,
+  shouldShowAnonymousCalendarChangeSignUpPrompt,
+  subscribeToAuthState,
   updateAuthState,
 } from "./auth.state.util";
 
@@ -39,7 +43,10 @@ describe("auth-state.util", () => {
       localStorage.setItem(STORAGE_KEYS.AUTH, JSON.stringify(testState));
 
       const state = getAuthState();
-      expect(state).toEqual(testState);
+      expect(state).toEqual({
+        hasAuthenticated: true,
+        shouldPromptSignUpAfterAnonymousCalendarChange: false,
+      });
     });
 
     it("should migrate legacy stored state from isGoogleAuthenticated", () => {
@@ -48,7 +55,10 @@ describe("auth-state.util", () => {
         JSON.stringify({ isGoogleAuthenticated: true }),
       );
 
-      expect(getAuthState()).toEqual({ hasAuthenticated: true });
+      expect(getAuthState()).toEqual({
+        hasAuthenticated: true,
+        shouldPromptSignUpAfterAnonymousCalendarChange: false,
+      });
     });
 
     it("should handle invalid JSON gracefully", () => {
@@ -73,7 +83,12 @@ describe("auth-state.util", () => {
 
       const stored = localStorage.getItem(STORAGE_KEYS.AUTH);
       expect(stored).toBeTruthy();
-      const parsed = JSON.parse(stored!);
+      const parsed: unknown = JSON.parse(stored ?? "{}");
+      expect(typeof parsed).toBe("object");
+      expect(parsed).not.toBeNull();
+      if (typeof parsed !== "object" || parsed === null) {
+        throw new Error("Expected parsed auth state to be an object");
+      }
       expect(parsed.hasAuthenticated).toBe(true);
     });
 
@@ -94,6 +109,7 @@ describe("auth-state.util", () => {
       expect(getAuthState()).toEqual({
         hasAuthenticated: true,
         lastKnownEmail: "foo@bar.com",
+        shouldPromptSignUpAfterAnonymousCalendarChange: false,
       });
     });
 
@@ -146,6 +162,37 @@ describe("auth-state.util", () => {
     });
   });
 
+  describe("anonymous calendar sign-up prompt", () => {
+    it("defaults the prompt flag to false for legacy state", () => {
+      localStorage.setItem(
+        STORAGE_KEYS.AUTH,
+        JSON.stringify({ hasAuthenticated: false }),
+      );
+
+      expect(shouldShowAnonymousCalendarChangeSignUpPrompt()).toBe(false);
+    });
+
+    it("marks and clears the prompt flag", () => {
+      markAnonymousCalendarChangeForSignUpPrompt();
+      expect(shouldShowAnonymousCalendarChangeSignUpPrompt()).toBe(true);
+
+      clearAnonymousCalendarChangeSignUpPrompt();
+      expect(shouldShowAnonymousCalendarChangeSignUpPrompt()).toBe(false);
+    });
+
+    it("notifies subscribers when auth state changes", () => {
+      const listener = jest.fn();
+      const unsubscribe = subscribeToAuthState(listener);
+
+      markAnonymousCalendarChangeForSignUpPrompt();
+      clearAnonymousCalendarChangeSignUpPrompt();
+
+      expect(listener).toHaveBeenCalledTimes(2);
+
+      unsubscribe();
+    });
+  });
+
   describe("hasUserEverAuthenticated", () => {
     it("should return true when authentication flag is set", () => {
       updateAuthState({ hasAuthenticated: true });
diff --git a/packages/web/src/auth/state/auth.state.util.ts b/packages/web/src/auth/compass/state/auth.state.util.ts
similarity index 69%
rename from packages/web/src/auth/state/auth.state.util.ts
rename to packages/web/src/auth/compass/state/auth.state.util.ts
index ed9fe48e2..cfc957eca 100644
--- a/packages/web/src/auth/state/auth.state.util.ts
+++ b/packages/web/src/auth/compass/state/auth.state.util.ts
@@ -4,7 +4,13 @@ import {
   DEFAULT_AUTH_STATE,
 } from "@web/common/constants/auth.constants";
 import { STORAGE_KEYS } from "@web/common/constants/storage.constants";
-import { clearGoogleRevokedState } from "../google/google.auth.state";
+import { clearGoogleRevokedState } from "../../google/state/google.auth.state";
+
+const authStateListeners = new Set<() => void>();
+
+function emitAuthStateChange(): void {
+  authStateListeners.forEach((listener) => listener());
+}
 
 function normalizeStoredAuthState(parsed: unknown): AuthState {
   if (typeof parsed !== "object" || parsed === null) {
@@ -15,6 +21,7 @@ function normalizeStoredAuthState(parsed: unknown): AuthState {
     isGoogleAuthenticated?: unknown;
     hasAuthenticated?: unknown;
     lastKnownEmail?: unknown;
+    shouldPromptSignUpAfterAnonymousCalendarChange?: unknown;
   };
 
   // Migrate legacy isGoogleAuthenticated to hasAuthenticated
@@ -28,6 +35,8 @@ function normalizeStoredAuthState(parsed: unknown): AuthState {
   const migratedState = {
     hasAuthenticated,
     lastKnownEmail: legacyState.lastKnownEmail,
+    shouldPromptSignUpAfterAnonymousCalendarChange:
+      legacyState.shouldPromptSignUpAfterAnonymousCalendarChange,
   };
 
   const result = AuthStateSchema.safeParse(migratedState);
@@ -44,7 +53,7 @@ export function getAuthState(): AuthState {
   try {
     const stored = localStorage.getItem(STORAGE_KEYS.AUTH);
     if (stored) {
-      const parsed = JSON.parse(stored);
+      const parsed: unknown = JSON.parse(stored);
       return normalizeStoredAuthState(parsed);
     }
 
@@ -72,6 +81,7 @@ export function updateAuthState(updates: Partial<AuthState>): void {
     const result = AuthStateSchema.safeParse(updated);
     if (result.success) {
       localStorage.setItem(STORAGE_KEYS.AUTH, JSON.stringify(result.data));
+      emitAuthStateChange();
     }
   } catch {
     // Silently fail if localStorage is unavailable
@@ -129,7 +139,47 @@ export function clearAuthenticationState(): void {
 
   try {
     localStorage.removeItem(STORAGE_KEYS.AUTH);
+    emitAuthStateChange();
   } catch {
     // Silently fail if localStorage is unavailable
   }
 }
+
+export function clearAnonymousCalendarChangeSignUpPrompt(): void {
+  updateAuthState({ shouldPromptSignUpAfterAnonymousCalendarChange: false });
+}
+
+export function markAnonymousCalendarChangeForSignUpPrompt(): void {
+  updateAuthState({ shouldPromptSignUpAfterAnonymousCalendarChange: true });
+}
+
+export function shouldShowAnonymousCalendarChangeSignUpPrompt(): boolean {
+  try {
+    return getAuthState().shouldPromptSignUpAfterAnonymousCalendarChange;
+  } catch {
+    return false;
+  }
+}
+
+export function subscribeToAuthState(listener: () => void): () => void {
+  authStateListeners.add(listener);
+
+  if (typeof window === "undefined") {
+    return () => {
+      authStateListeners.delete(listener);
+    };
+  }
+
+  const handleStorage = (event: StorageEvent) => {
+    if (event.key === STORAGE_KEYS.AUTH) {
+      listener();
+    }
+  };
+
+  window.addEventListener("storage", handleStorage);
+
+  return () => {
+    authStateListeners.delete(listener);
+    window.removeEventListener("storage", handleStorage);
+  };
+}
diff --git a/packages/web/src/auth/context/UserContext.tsx b/packages/web/src/auth/compass/user/context/UserContext.tsx
similarity index 58%
rename from packages/web/src/auth/context/UserContext.tsx
rename to packages/web/src/auth/compass/user/context/UserContext.tsx
index f222ba219..d9b57eeb2 100644
--- a/packages/web/src/auth/context/UserContext.tsx
+++ b/packages/web/src/auth/compass/user/context/UserContext.tsx
@@ -2,8 +2,5 @@ import { createContext } from "react";
 import { type UserProfile } from "@core/types/user.types";
 
 export const UserContext = createContext<
-  | Partial<
-      { isLoadingUser: boolean; userId: string } & Omit<UserProfile, "_id">
-    >
-  | undefined
+  Partial<{ userId: string } & Omit<UserProfile, "_id">> | undefined
 >(undefined);
diff --git a/packages/web/src/auth/compass/user/context/UserProvider.test.tsx b/packages/web/src/auth/compass/user/context/UserProvider.test.tsx
new file mode 100644
index 000000000..5ab5a53c8
--- /dev/null
+++ b/packages/web/src/auth/compass/user/context/UserProvider.test.tsx
@@ -0,0 +1,79 @@
+import "@testing-library/jest-dom";
+import { render, screen, waitFor } from "@testing-library/react";
+import { useSession } from "@web/auth/compass/session/useSession";
+import * as authStateUtil from "@web/auth/compass/state/auth.state.util";
+import { UserProvider } from "@web/auth/compass/user/context/UserProvider";
+import { useUser } from "@web/auth/compass/user/hooks/useUser";
+
+jest.mock("@web/auth/compass/session/useSession", () => ({
+  useSession: jest.fn(),
+}));
+const mockUseSession = jest.mocked(useSession);
+
+jest.mock("@web/auth/compass/state/auth.state.util", () => {
+  const actual = jest.requireActual<typeof authStateUtil>(
+    "@web/auth/compass/state/auth.state.util",
+  );
+  return {
+    ...actual,
+    getLastKnownEmail: jest.fn(),
+    hasUserEverAuthenticated: jest.fn(),
+  };
+});
+const mockGetLastKnownEmail = jest.mocked(authStateUtil.getLastKnownEmail);
+const mockHasUserEverAuthenticated = jest.mocked(
+  authStateUtil.hasUserEverAuthenticated,
+);
+
+const UserEmail = () => <div>{useUser().email ?? "no-email"}</div>;
+
+describe("UserProvider", () => {
+  let isAuthenticated = false;
+
+  beforeEach(() => {
+    jest.clearAllMocks();
+    isAuthenticated = false;
+    mockGetLastKnownEmail.mockReturnValue("last-known@example.com");
+    mockHasUserEverAuthenticated.mockReturnValue(true);
+    mockUseSession.mockImplementation(() => ({
+      authenticated: isAuthenticated,
+      setAuthenticated: jest.fn(),
+    }));
+  });
+
+  it("renders children", () => {
+    render(
+      <UserProvider>
+        <div>Test Child</div>
+      </UserProvider>,
+    );
+
+    expect(screen.getByText("Test Child")).toBeInTheDocument();
+  });
+
+  it("fetches the profile when session auth completes after mount (hasAuthenticatedBefore becomes true)", async () => {
+    mockHasUserEverAuthenticated.mockReturnValue(false);
+
+    const { rerender } = render(
+      <UserProvider>
+        <UserEmail />
+      </UserProvider>,
+    );
+
+    await waitFor(() => {
+      expect(screen.getByText("no-email")).toBeInTheDocument();
+    });
+
+    isAuthenticated = true;
+
+    rerender(
+      <UserProvider>
+        <UserEmail />
+      </UserProvider>,
+    );
+
+    await waitFor(() => {
+      expect(screen.getByText("test@example.com")).toBeInTheDocument();
+    });
+  });
+});
diff --git a/packages/web/src/auth/compass/user/context/UserProvider.tsx b/packages/web/src/auth/compass/user/context/UserProvider.tsx
new file mode 100644
index 000000000..c66ae375f
--- /dev/null
+++ b/packages/web/src/auth/compass/user/context/UserProvider.tsx
@@ -0,0 +1,27 @@
+import { type ReactNode } from "react";
+import { useSession } from "@web/auth/compass/session/useSession";
+import { hasUserEverAuthenticated } from "@web/auth/compass/state/auth.state.util";
+import { useLoadProfile } from "@web/auth/compass/user/hooks/useLoadProfile";
+import { useIdentifyUser } from "@web/auth/posthog/useIdentifyUser";
+import { UserContext } from "./UserContext";
+
+export const UserProvider = ({ children }: { children: ReactNode }) => {
+  const { authenticated } = useSession();
+  const hasAuthenticatedBefore = authenticated || hasUserEverAuthenticated();
+  const { email, profile, profileEmail, userId } = useLoadProfile(
+    hasAuthenticatedBefore,
+  );
+  useIdentifyUser(profileEmail, userId);
+
+  return (
+    <UserContext.Provider
+      value={{
+        ...(profile ?? {}),
+        email: email ?? undefined,
+        userId: userId ?? undefined,
+      }}
+    >
+      {children}
+    </UserContext.Provider>
+  );
+};
diff --git a/packages/web/src/auth/compass/user/hooks/useLoadProfile.test.ts b/packages/web/src/auth/compass/user/hooks/useLoadProfile.test.ts
new file mode 100644
index 000000000..479d5407a
--- /dev/null
+++ b/packages/web/src/auth/compass/user/hooks/useLoadProfile.test.ts
@@ -0,0 +1,196 @@
+import { rest } from "msw";
+import { type ReactElement, isValidElement } from "react";
+import { toast } from "react-toastify";
+import "@testing-library/jest-dom";
+import { renderHook, waitFor } from "@testing-library/react";
+import { Status } from "@core/errors/status.codes";
+// eslint-disable-next-line jest/no-mocks-import
+import { server } from "@web/__tests__/__mocks__/server/mock.server";
+import * as authStateUtil from "@web/auth/compass/state/auth.state.util";
+import { UserApi } from "@web/common/apis/user.api";
+import { ENV_WEB } from "@web/common/constants/env.constants";
+import { SessionExpiredToast } from "@web/common/utils/toast/session-expired.toast";
+import { useLoadProfile } from "./useLoadProfile";
+
+jest.mock("@web/auth/compass/state/auth.state.util", () => {
+  const actual = jest.requireActual<typeof authStateUtil>(
+    "@web/auth/compass/state/auth.state.util",
+  );
+  return {
+    ...actual,
+    getLastKnownEmail: jest.fn(),
+  };
+});
+const mockGetLastKnownEmail = jest.mocked(authStateUtil.getLastKnownEmail);
+
+const mockToastError = jest.mocked(toast.error);
+
+describe("useLoadProfile", () => {
+  beforeEach(() => {
+    jest.clearAllMocks();
+    mockGetLastKnownEmail.mockReturnValue("last-known@example.com");
+  });
+
+  it("does not call getProfile when user has never authenticated", async () => {
+    const getProfileSpy = jest.spyOn(UserApi, "getProfile");
+
+    renderHook(() => useLoadProfile(false));
+
+    await waitFor(() => {
+      expect(getProfileSpy).not.toHaveBeenCalled();
+    });
+
+    getProfileSpy.mockRestore();
+  });
+
+  it("calls getProfile when hasAuthenticatedBefore is true", async () => {
+    const getProfileSpy = jest.spyOn(UserApi, "getProfile");
+
+    renderHook(() => useLoadProfile(true));
+
+    await waitFor(() => expect(getProfileSpy).toHaveBeenCalled());
+    expect(getProfileSpy).toHaveBeenCalledTimes(1);
+
+    getProfileSpy.mockRestore();
+  });
+
+  it("fetches the profile when hasAuthenticatedBefore becomes true after mount", async () => {
+    const getProfileSpy = jest.spyOn(UserApi, "getProfile");
+
+    const { result, rerender } = renderHook(
+      ({ hasAuthenticatedBefore }: { hasAuthenticatedBefore: boolean }) =>
+        useLoadProfile(hasAuthenticatedBefore),
+      { initialProps: { hasAuthenticatedBefore: false } },
+    );
+
+    await waitFor(() => {
+      expect(result.current.email).toBeNull();
+    });
+    expect(getProfileSpy).not.toHaveBeenCalled();
+
+    rerender({ hasAuthenticatedBefore: true });
+
+    await waitFor(() => expect(getProfileSpy).toHaveBeenCalledTimes(1));
+    await waitFor(() => {
+      expect(result.current.email).toBe("test@example.com");
+    });
+
+    getProfileSpy.mockRestore();
+  });
+
+  it("shows the last known email while the profile is loading", async () => {
+    server.use(
+      rest.get(`${ENV_WEB.API_BASEURL}/user/profile`, (_req, res, ctx) => {
+        return res(
+          ctx.delay(100),
+          ctx.status(Status.OK),
+          ctx.json({
+            userId: "test-user-123",
+            email: "test@example.com",
+          }),
+        );
+      }),
+    );
+
+    const { result } = renderHook(() => useLoadProfile(true));
+
+    expect(result.current.email).toBe("last-known@example.com");
+
+    await waitFor(() => {
+      expect(result.current.email).toBe("test@example.com");
+    });
+  });
+
+  it("returns profile without email when the API omits email", async () => {
+    server.use(
+      rest.get(`${ENV_WEB.API_BASEURL}/user/profile`, (_req, res, ctx) => {
+        return res(
+          ctx.status(Status.OK),
+          ctx.json({ userId: "test-user-123" }),
+        );
+      }),
+    );
+
+    const { result } = renderHook(() => useLoadProfile(true));
+
+    await waitFor(() => {
+      expect(result.current.profile).not.toBeNull();
+    });
+    expect(result.current.profileEmail).toBeNull();
+    expect(result.current.userId).toBe("test-user-123");
+  });
+
+  it("returns profile without userId when the API omits userId", async () => {
+    const getProfileSpy = jest.spyOn(UserApi, "getProfile");
+    server.use(
+      rest.get(`${ENV_WEB.API_BASEURL}/user/profile`, (_req, res, ctx) => {
+        return res(
+          ctx.status(Status.OK),
+          ctx.json({ email: "test@example.com" }),
+        );
+      }),
+    );
+
+    const { result } = renderHook(() => useLoadProfile(true));
+
+    await waitFor(() => expect(getProfileSpy).toHaveBeenCalled());
+    await getProfileSpy.mock.results[0].value;
+
+    await waitFor(() => {
+      expect(result.current.profile).not.toBeNull();
+    });
+    expect(result.current.userId).toBeNull();
+    expect(result.current.profileEmail).toBe("test@example.com");
+
+    getProfileSpy.mockRestore();
+  });
+
+  it("shows a login toast when profile fetch returns unauthorized", async () => {
+    const assignMock = jest.fn();
+    const originalLocation = window.location;
+    Object.defineProperty(window, "location", {
+      value: { ...originalLocation, assign: assignMock },
+      configurable: true,
+    });
+
+    const getProfileSpy = jest.spyOn(UserApi, "getProfile");
+    server.use(
+      rest.get(`${ENV_WEB.API_BASEURL}/user/profile`, (_req, res, ctx) => {
+        return res(ctx.status(Status.UNAUTHORIZED));
+      }),
+    );
+
+    renderHook(() => useLoadProfile(true));
+
+    await waitFor(() => expect(getProfileSpy).toHaveBeenCalled());
+    try {
+      await getProfileSpy.mock.results[0].value;
+    } catch {
+      // expected — profile fetch rejects on 401
+    }
+
+    expect(mockToastError).toHaveBeenCalled();
+    const latestToastCall =
+      mockToastError.mock.calls[mockToastError.mock.calls.length - 1];
+    expect(latestToastCall[1]).toEqual(
+      expect.objectContaining({
+        toastId: "session-expired-api",
+        autoClose: false,
+        closeOnClick: false,
+        draggable: false,
+      }),
+    );
+
+    const toastContent = latestToastCall[0];
+    expect(isValidElement(toastContent)).toBe(true);
+    const toastElement = toastContent as ReactElement<{ toastId: string }>;
+    expect(toastElement.type).toBe(SessionExpiredToast);
+    expect(toastElement.props.toastId).toBe("session-expired-api");
+
+    getProfileSpy.mockRestore();
+    Object.defineProperty(window, "location", {
+      value: originalLocation,
+      configurable: true,
+    });
+  });
+});
diff --git a/packages/web/src/auth/compass/user/hooks/useLoadProfile.ts b/packages/web/src/auth/compass/user/hooks/useLoadProfile.ts
new file mode 100644
index 000000000..f258b08fc
--- /dev/null
+++ b/packages/web/src/auth/compass/user/hooks/useLoadProfile.ts
@@ -0,0 +1,84 @@
+import { useCallback, useLayoutEffect, useRef, useState } from "react";
+import { Status } from "@core/errors/status.codes";
+import { type UserProfile } from "@core/types/user.types";
+import {
+  getLastKnownEmail,
+  markUserAsAuthenticated,
+} from "@web/auth/compass/state/auth.state.util";
+import { UserApi } from "@web/common/apis/user.api";
+import { showSessionExpiredToast } from "@web/common/utils/toast/error-toast.util";
+
+export type UseLoadProfileResult = {
+  email: string | null;
+  profile: UserProfile | null;
+  profileEmail: string | null;
+  userId: string | null;
+};
+
+/**
+ * Fetches the authenticated user profile when `hasAuthenticatedBefore` is true.
+ * While loading, exposes the last known email from storage when available.
+ */
+export function useLoadProfile(
+  hasAuthenticatedBefore: boolean,
+): UseLoadProfileResult {
+  const [profile, setProfile] = useState<UserProfile | null>(null);
+  const [isLoadingUser, setIsLoadingUser] = useState(hasAuthenticatedBefore);
+  const profileRequest = useRef<Promise<void> | null>(null);
+  const userId = profile?.userId ?? null;
+  const profileEmail = profile?.email ?? null;
+  const email =
+    profileEmail ??
+    (profile === null && isLoadingUser ? (getLastKnownEmail() ?? null) : null);
+
+  const loadProfile = useCallback(() => {
+    if (profileRequest.current) {
+      return profileRequest.current;
+    }
+
+    setIsLoadingUser(true);
+
+    profileRequest.current = UserApi.getProfile()
+      .then((userProfile) => {
+        setProfile(userProfile);
+        markUserAsAuthenticated(userProfile.email);
+      })
+      .catch((e) => {
+        const status = (e as { response?: { status?: number } })?.response
+          ?.status;
+        const isUnauthorized =
+          status === Status.UNAUTHORIZED || status === Status.FORBIDDEN;
+
+        if (isUnauthorized) {
+          showSessionExpiredToast();
+          return;
+        }
+
+        console.error("Failed to get user profile", e);
+      })
+      .finally(() => {
+        profileRequest.current = null;
+        setIsLoadingUser(false);
+      });
+
+    return profileRequest.current;
+  }, []);
+
+  useLayoutEffect(() => {
+    if (profile) return;
+
+    if (!hasAuthenticatedBefore) {
+      setIsLoadingUser(false);
+      return;
+    }
+
+    void loadProfile();
+  }, [hasAuthenticatedBefore, loadProfile, profile]);
+
+  return {
+    email,
+    profile,
+    profileEmail,
+    userId,
+  };
+}
diff --git a/packages/web/src/auth/hooks/user/useUser.test.tsx b/packages/web/src/auth/compass/user/hooks/useUser.test.tsx
similarity index 91%
rename from packages/web/src/auth/hooks/user/useUser.test.tsx
rename to packages/web/src/auth/compass/user/hooks/useUser.test.tsx
index 8969968b4..61dbef7a5 100644
--- a/packages/web/src/auth/hooks/user/useUser.test.tsx
+++ b/packages/web/src/auth/compass/user/hooks/useUser.test.tsx
@@ -1,5 +1,5 @@
 import { renderHook } from "@testing-library/react";
-import { UserContext } from "../../context/UserContext";
+import { UserContext } from "../context/UserContext";
 import { useUser } from "./useUser";
 
 describe("useUser", () => {
@@ -7,7 +7,6 @@ describe("useUser", () => {
     const mockUser = {
       userId: "user123",
       email: "test@example.com",
-      isLoadingUser: false,
     };
     const wrapper = ({ children }: { children: React.ReactNode }) => (
       <UserContext.Provider value={mockUser}>{children}</UserContext.Provider>
diff --git a/packages/web/src/auth/hooks/user/useUser.ts b/packages/web/src/auth/compass/user/hooks/useUser.ts
similarity index 80%
rename from packages/web/src/auth/hooks/user/useUser.ts
rename to packages/web/src/auth/compass/user/hooks/useUser.ts
index 5e0aa9146..e9d81d061 100644
--- a/packages/web/src/auth/hooks/user/useUser.ts
+++ b/packages/web/src/auth/compass/user/hooks/useUser.ts
@@ -1,5 +1,5 @@
 import { useContext } from "react";
-import { UserContext } from "../../context/UserContext";
+import { UserContext } from "../context/UserContext";
 
 export const useUser = () => {
   const context = useContext(UserContext);
diff --git a/packages/web/src/auth/compass/user/util/user-metadata.import.util.test.ts b/packages/web/src/auth/compass/user/util/user-metadata.import.util.test.ts
new file mode 100644
index 000000000..b0264679d
--- /dev/null
+++ b/packages/web/src/auth/compass/user/util/user-metadata.import.util.test.ts
@@ -0,0 +1,65 @@
+import { isGoogleCalendarImportActive } from "./user-metadata.import.util";
+
+describe("isGoogleCalendarImportActive", () => {
+  it("returns true when import is actively running", () => {
+    expect(
+      isGoogleCalendarImportActive({
+        google: { connectionState: "HEALTHY" },
+        sync: { importGCal: "IMPORTING" },
+      }),
+    ).toBe(true);
+  });
+
+  it("returns false for RESTART — import hasn't started yet, no spinner", () => {
+    // RESTART means the backend wants to re-import, not that it's running.
+    // Showing a spinner for RESTART caused visible flicker before this fix.
+    expect(
+      isGoogleCalendarImportActive({
+        google: { connectionState: "ATTENTION" },
+        sync: { importGCal: "RESTART" },
+      }),
+    ).toBe(false);
+  });
+
+  it("returns false when COMPLETED", () => {
+    expect(
+      isGoogleCalendarImportActive({
+        google: { connectionState: "HEALTHY" },
+        sync: { importGCal: "COMPLETED" },
+      }),
+    ).toBe(false);
+  });
+
+  it("returns false when ERRORED", () => {
+    expect(
+      isGoogleCalendarImportActive({
+        google: { connectionState: "HEALTHY" },
+        sync: { importGCal: "ERRORED" },
+      }),
+    ).toBe(false);
+  });
+
+  it("returns false when sync status is absent", () => {
+    expect(
+      isGoogleCalendarImportActive({ google: { connectionState: "HEALTHY" } }),
+    ).toBe(false);
+  });
+
+  it("returns false when IMPORTING but Google is not connected", () => {
+    expect(
+      isGoogleCalendarImportActive({
+        google: { connectionState: "NOT_CONNECTED" },
+        sync: { importGCal: "IMPORTING" },
+      }),
+    ).toBe(false);
+  });
+
+  it("returns false when IMPORTING but reconnect is required", () => {
+    expect(
+      isGoogleCalendarImportActive({
+        google: { connectionState: "RECONNECT_REQUIRED" },
+        sync: { importGCal: "IMPORTING" },
+      }),
+    ).toBe(false);
+  });
+});
diff --git a/packages/web/src/auth/compass/user/util/user-metadata.import.util.ts b/packages/web/src/auth/compass/user/util/user-metadata.import.util.ts
new file mode 100644
index 000000000..09c7591f1
--- /dev/null
+++ b/packages/web/src/auth/compass/user/util/user-metadata.import.util.ts
@@ -0,0 +1,16 @@
+import { type UserMetadata } from "@core/types/user.types";
+
+const isGoogleConnected = (metadata: UserMetadata) => {
+  const connectionState = metadata.google?.connectionState;
+  return (
+    connectionState !== "NOT_CONNECTED" &&
+    connectionState !== "RECONNECT_REQUIRED"
+  );
+};
+
+/** Returns true when an import is actively in progress (show spinner). */
+export const isGoogleCalendarImportActive = (metadata: UserMetadata) => {
+  return (
+    metadata.sync?.importGCal === "IMPORTING" && isGoogleConnected(metadata)
+  );
+};
diff --git a/packages/web/src/auth/session/user-metadata.util.test.ts b/packages/web/src/auth/compass/user/util/user-metadata.util.test.ts
similarity index 61%
rename from packages/web/src/auth/session/user-metadata.util.test.ts
rename to packages/web/src/auth/compass/user/util/user-metadata.util.test.ts
index 3507c6b0f..ad7aaa764 100644
--- a/packages/web/src/auth/session/user-metadata.util.test.ts
+++ b/packages/web/src/auth/compass/user/util/user-metadata.util.test.ts
@@ -1,4 +1,5 @@
 import { Status } from "@core/errors/status.codes";
+import { resetGoogleSyncUIStateForTests } from "@web/auth/google/state/google.sync.state";
 import { UserApi } from "@web/common/apis/user.api";
 import { store } from "@web/store";
 import { refreshUserMetadata } from "./user-metadata.util";
@@ -16,14 +17,12 @@ jest.mock("@web/store", () => ({
 }));
 
 describe("refreshUserMetadata", () => {
-  const api = UserApi as unknown as {
-    getMetadata: jest.MockedFunction<typeof UserApi.getMetadata>;
-  };
-  const getDispatchMock = () =>
-    store.dispatch as jest.MockedFunction<typeof store.dispatch>;
+  const api = UserApi as jest.Mocked<typeof UserApi>;
+  const dispatch = store.dispatch as jest.MockedFunction<typeof store.dispatch>;
 
   beforeEach(() => {
     jest.clearAllMocks();
+    resetGoogleSyncUIStateForTests();
   });
 
   it("loads metadata into the store", async () => {
@@ -36,15 +35,35 @@ describe("refreshUserMetadata", () => {
 
     await refreshUserMetadata();
 
-    expect(getDispatchMock()).toHaveBeenNthCalledWith(
+    expect(dispatch).toHaveBeenNthCalledWith(
       1,
       expect.objectContaining({ type: "userMetadata/setLoading" }),
     );
-    expect(getDispatchMock()).toHaveBeenNthCalledWith(
+    expect(dispatch).toHaveBeenNthCalledWith(
+      2,
+      expect.objectContaining({ type: "userMetadata/set", payload: metadata }),
+    );
+    expect(dispatch).toHaveBeenCalledTimes(2);
+  });
+
+  it("does not trigger a client-side import when metadata says RESTART", async () => {
+    const metadata = {
+      google: {
+        connectionState: "ATTENTION" as const,
+      },
+      sync: {
+        importGCal: "RESTART" as const,
+      },
+    };
+    api.getMetadata.mockResolvedValue(metadata);
+
+    await refreshUserMetadata();
+    await refreshUserMetadata();
+
+    expect(dispatch).toHaveBeenNthCalledWith(
       2,
       expect.objectContaining({ type: "userMetadata/set", payload: metadata }),
     );
-    expect(getDispatchMock()).toHaveBeenCalledTimes(2);
   });
 
   it("clears metadata when the request is unauthorized", async () => {
@@ -56,11 +75,11 @@ describe("refreshUserMetadata", () => {
 
     await refreshUserMetadata();
 
-    expect(getDispatchMock()).toHaveBeenNthCalledWith(
+    expect(dispatch).toHaveBeenNthCalledWith(
       1,
       expect.objectContaining({ type: "userMetadata/setLoading" }),
     );
-    expect(getDispatchMock()).toHaveBeenNthCalledWith(
+    expect(dispatch).toHaveBeenNthCalledWith(
       2,
       expect.objectContaining({ type: "userMetadata/clear" }),
     );
@@ -74,11 +93,11 @@ describe("refreshUserMetadata", () => {
 
     await refreshUserMetadata();
 
-    expect(getDispatchMock()).toHaveBeenNthCalledWith(
+    expect(dispatch).toHaveBeenNthCalledWith(
       1,
       expect.objectContaining({ type: "userMetadata/setLoading" }),
     );
-    expect(getDispatchMock()).toHaveBeenNthCalledWith(
+    expect(dispatch).toHaveBeenNthCalledWith(
       2,
       expect.objectContaining({ type: "userMetadata/finishLoading" }),
     );
diff --git a/packages/web/src/auth/session/user-metadata.util.ts b/packages/web/src/auth/compass/user/util/user-metadata.util.ts
similarity index 100%
rename from packages/web/src/auth/session/user-metadata.util.ts
rename to packages/web/src/auth/compass/user/util/user-metadata.util.ts
diff --git a/packages/web/src/auth/context/UserProvider.test.tsx b/packages/web/src/auth/context/UserProvider.test.tsx
deleted file mode 100644
index a4d588c6a..000000000
--- a/packages/web/src/auth/context/UserProvider.test.tsx
+++ /dev/null
@@ -1,290 +0,0 @@
-import { rest } from "msw";
-import { type PostHog } from "posthog-js";
-import { usePostHog } from "posthog-js/react";
-import { act, isValidElement } from "react";
-import { toast } from "react-toastify";
-import "@testing-library/jest-dom";
-import { render, screen, waitFor } from "@testing-library/react";
-import { Status } from "@core/errors/status.codes";
-import { server } from "@web/__tests__/__mocks__/server/mock.server";
-import { UserProvider } from "@web/auth/context/UserProvider";
-import * as authStateUtil from "@web/auth/state/auth.state.util";
-import { UserApi } from "@web/common/apis/user.api";
-import { ENV_WEB } from "@web/common/constants/env.constants";
-import { SessionExpiredToast } from "@web/common/utils/toast/session-expired.toast";
-
-jest.mock("posthog-js/react");
-const mockUsePostHog = jest.mocked(usePostHog);
-const mockToastError = jest.mocked(toast.error);
-
-jest.mock("@web/auth/state/auth.state.util", () => {
-  const actual = jest.requireActual<typeof authStateUtil>(
-    "@web/auth/state/auth.state.util",
-  );
-  return {
-    ...actual,
-    hasUserEverAuthenticated: jest.fn(),
-  };
-});
-const mockHasUserEverAuthenticated = jest.mocked(
-  authStateUtil.hasUserEverAuthenticated,
-);
-
-// Mock AbsoluteOverflowLoader
-jest.mock("@web/components/AbsoluteOverflowLoader", () => ({
-  AbsoluteOverflowLoader: () => <div>Loading...</div>,
-}));
-
-const mockIdentify = jest.fn();
-
-function mockPostHogEnabled(overrides?: Partial<PostHog>): void {
-  mockUsePostHog.mockReturnValue({
-    identify: mockIdentify,
-    ...overrides,
-  } as unknown as PostHog);
-}
-
-function mockPostHogDisabled(): void {
-  mockUsePostHog.mockReturnValue(undefined as unknown as PostHog);
-}
-
-describe("UserProvider", () => {
-  beforeEach(() => {
-    jest.clearAllMocks();
-    mockHasUserEverAuthenticated.mockReturnValue(true);
-    mockPostHogEnabled();
-  });
-
-  describe("PostHog Integration", () => {
-    it("should call posthog.identify when PostHog is enabled and user data is available", async () => {
-      const testUserId = "test-user-123";
-      const testEmail = "test@example.com";
-
-      render(
-        <UserProvider>
-          <div>Test Child</div>
-        </UserProvider>,
-      );
-
-      await waitFor(() => {
-        expect(screen.getByText("Test Child")).toBeInTheDocument();
-      });
-
-      expect(mockIdentify).toHaveBeenCalledWith(testEmail, {
-        email: testEmail,
-        userId: testUserId,
-      });
-
-      expect(mockIdentify).toHaveBeenCalledTimes(1);
-    });
-
-    it("should NOT call posthog.identify when PostHog is disabled", async () => {
-      mockPostHogDisabled();
-
-      render(
-        <UserProvider>
-          <div>Test Child</div>
-        </UserProvider>,
-      );
-
-      await waitFor(() => {
-        expect(screen.getByText("Test Child")).toBeInTheDocument();
-      });
-
-      expect(mockIdentify).not.toHaveBeenCalled();
-    });
-
-    it("should NOT call posthog.identify when email is missing from session", async () => {
-      server.use(
-        rest.get(`${ENV_WEB.API_BASEURL}/user/profile`, (_req, res, ctx) => {
-          return res(
-            ctx.status(Status.OK),
-            ctx.json({ userId: "test-user-123" }),
-          );
-        }),
-      );
-
-      render(
-        <UserProvider>
-          <div>Test Child</div>
-        </UserProvider>,
-      );
-
-      await waitFor(() => {
-        expect(screen.getByText("Test Child")).toBeInTheDocument();
-      });
-
-      expect(mockIdentify).not.toHaveBeenCalled();
-    });
-
-    it("should NOT call posthog.identify when userId is missing", async () => {
-      const getProfileSpy = jest.spyOn(UserApi, "getProfile");
-      server.use(
-        rest.get(`${ENV_WEB.API_BASEURL}/user/profile`, (_req, res, ctx) => {
-          return res(
-            ctx.status(Status.OK),
-            ctx.json({ email: "test@example.com" }),
-          );
-        }),
-      );
-
-      render(
-        <UserProvider>
-          <div>Test Child</div>
-        </UserProvider>,
-      );
-
-      await waitFor(() => expect(getProfileSpy).toHaveBeenCalled());
-      await getProfileSpy.mock.results[0].value;
-
-      expect(mockIdentify).not.toHaveBeenCalled();
-      getProfileSpy.mockRestore();
-    });
-
-    it("should handle posthog.identify not being a function gracefully", async () => {
-      mockPostHogEnabled({
-        identify: null as unknown as PostHog["identify"],
-      });
-
-      expect(() => {
-        render(
-          <UserProvider>
-            <div>Test Child</div>
-          </UserProvider>,
-        );
-      }).not.toThrow();
-
-      await waitFor(() => {
-        expect(screen.getByText("Test Child")).toBeInTheDocument();
-      });
-
-      expect(mockIdentify).not.toHaveBeenCalled();
-    });
-
-    it("should render children after user data is loaded", async () => {
-      server.use(
-        rest.get(`${ENV_WEB.API_BASEURL}/user/profile`, (_req, res, ctx) => {
-          return waitFor(
-            () =>
-              res(
-                ctx.status(Status.OK),
-                ctx.json({
-                  userId: "test-user-123",
-                  email: "test@example.com",
-                }),
-              ),
-            { timeout: 100 },
-          );
-        }),
-      );
-
-      render(
-        <UserProvider>
-          <div>Test Child Content</div>
-        </UserProvider>,
-      );
-
-      expect(screen.getByText("Loading...")).toBeInTheDocument();
-
-      await waitFor(() => {
-        expect(screen.getByText("Test Child Content")).toBeInTheDocument();
-      });
-    });
-
-    it("shows a login toast when profile fetch returns unauthorized", async () => {
-      const assignMock = jest.fn();
-      const originalLocation = window.location;
-      Object.defineProperty(window, "location", {
-        value: { ...originalLocation, assign: assignMock },
-        configurable: true,
-      });
-
-      const getProfileSpy = jest.spyOn(UserApi, "getProfile");
-      server.use(
-        rest.get(`${ENV_WEB.API_BASEURL}/user/profile`, (_req, res, ctx) => {
-          return res(ctx.status(Status.UNAUTHORIZED));
-        }),
-      );
-
-      render(
-        <UserProvider>
-          <div>Test Child</div>
-        </UserProvider>,
-      );
-
-      await waitFor(() => expect(getProfileSpy).toHaveBeenCalled());
-      try {
-        await getProfileSpy.mock.results[0].value;
-      } catch {
-        // expected — profile fetch rejects on 401
-      }
-
-      expect(mockToastError).toHaveBeenCalled();
-      const latestToastCall =
-        mockToastError.mock.calls[mockToastError.mock.calls.length - 1];
-      expect(latestToastCall[1]).toEqual(
-        expect.objectContaining({
-          toastId: "session-expired-api",
-          autoClose: false,
-          closeOnClick: false,
-          draggable: false,
-        }),
-      );
-
-      const toastContent = latestToastCall[0];
-      expect(isValidElement(toastContent)).toBe(true);
-      if (isValidElement<{ toastId: string }>(toastContent)) {
-        expect(toastContent.type).toBe(SessionExpiredToast);
-        expect(toastContent.props.toastId).toBe("session-expired-api");
-      }
-
-      expect(mockIdentify).not.toHaveBeenCalled();
-
-      getProfileSpy.mockRestore();
-      Object.defineProperty(window, "location", {
-        value: originalLocation,
-        configurable: true,
-      });
-    });
-  });
-
-  describe("Authentication Gating", () => {
-    it("should NOT call getProfile when user has never authenticated", async () => {
-      mockHasUserEverAuthenticated.mockReturnValue(false);
-      const getProfileSpy = jest.spyOn(UserApi, "getProfile");
-
-      render(
-        <UserProvider>
-          <div>Test Child</div>
-        </UserProvider>,
-      );
-
-      await waitFor(() => {
-        expect(screen.getByText("Test Child")).toBeInTheDocument();
-      });
-
-      expect(getProfileSpy).not.toHaveBeenCalled();
-      getProfileSpy.mockRestore();
-    });
-
-    it("should call getProfile when user has authenticated with Google", async () => {
-      mockHasUserEverAuthenticated.mockReturnValue(true);
-      const getProfileSpy = jest.spyOn(UserApi, "getProfile");
-
-      render(
-        <UserProvider>
-          <div>Test Child</div>
-        </UserProvider>,
-      );
-
-      await waitFor(() => expect(getProfileSpy).toHaveBeenCalled());
-      expect(getProfileSpy).toHaveBeenCalledTimes(1);
-
-      await waitFor(() => {
-        expect(screen.getByText("Test Child")).toBeInTheDocument();
-      });
-
-      getProfileSpy.mockRestore();
-    });
-  });
-});
diff --git a/packages/web/src/auth/context/UserProvider.tsx b/packages/web/src/auth/context/UserProvider.tsx
deleted file mode 100644
index c57a6b273..000000000
--- a/packages/web/src/auth/context/UserProvider.tsx
+++ /dev/null
@@ -1,89 +0,0 @@
-import { usePostHog } from "posthog-js/react";
-import {
-  type ReactNode,
-  useEffect,
-  useLayoutEffect,
-  useRef,
-  useState,
-} from "react";
-import { Status } from "@core/errors/status.codes";
-import { type UserProfile } from "@core/types/user.types";
-import {
-  hasUserEverAuthenticated,
-  markUserAsAuthenticated,
-} from "@web/auth/state/auth.state.util";
-import { UserApi } from "@web/common/apis/user.api";
-import { showSessionExpiredToast } from "@web/common/utils/toast/error-toast.util";
-import { AbsoluteOverflowLoader } from "@web/components/AbsoluteOverflowLoader";
-import { UserContext } from "./UserContext";
-
-export const UserProvider = ({ children }: { children: ReactNode }) => {
-  const profile = useRef<UserProfile | null>(null);
-  const [isLoadingUser, setIsLoadingUser] = useState(false);
-  const posthog = usePostHog();
-  const userId = profile.current?.userId ?? null;
-  const email = profile.current?.email ?? null;
-
-  useLayoutEffect(() => {
-    if (profile.current) return;
-
-    // Only fetch profile if user has authenticated before.
-    if (!hasUserEverAuthenticated()) {
-      return;
-    }
-
-    setIsLoadingUser(true);
-
-    UserApi.getProfile()
-      .then((userProfile) => {
-        profile.current = userProfile;
-        markUserAsAuthenticated(userProfile.email);
-      })
-      .catch((e) => {
-        // Existing authenticated users can hit this when their session expires.
-        const status = (e as { response?: { status?: number } })?.response
-          ?.status;
-        const isUnauthorized =
-          status === Status.UNAUTHORIZED || status === Status.FORBIDDEN;
-
-        if (isUnauthorized) {
-          showSessionExpiredToast();
-          return;
-        }
-
-        console.error("Failed to get user profile", e);
-      })
-      .finally(() => {
-        setIsLoadingUser(false);
-      });
-  }, []);
-
-  // Identify user in PostHog when userId and email are available
-  // Only runs if PostHog is enabled (POSTHOG_HOST and POSTHOG_KEY are set)
-  useEffect(() => {
-    if (userId && email && posthog && typeof posthog.identify === "function") {
-      posthog.identify(email, { email, userId });
-    }
-  }, [userId, email, posthog]);
-
-  // Allow unauthenticated users to proceed without blocking
-  // Only show loader briefly while checking auth status
-  // Unauthenticated users will have profile.current === null, which is fine
-  if (isLoadingUser && userId === null) {
-    // Brief loading state - but don't block indefinitely
-    // The route loader handles auth redirects
-    return <AbsoluteOverflowLoader />;
-  }
-
-  return (
-    <UserContext.Provider
-      value={{
-        ...(profile.current ?? {}),
-        userId: userId ?? undefined,
-        isLoadingUser,
-      }}
-    >
-      {children}
-    </UserContext.Provider>
-  );
-};
diff --git a/packages/web/src/auth/hooks/google/googe.auth.types.ts b/packages/web/src/auth/google/hooks/googe.auth.types.ts
similarity index 100%
rename from packages/web/src/auth/hooks/google/googe.auth.types.ts
rename to packages/web/src/auth/google/hooks/googe.auth.types.ts
diff --git a/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.test.ts b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.test.ts
new file mode 100644
index 000000000..f05202303
--- /dev/null
+++ b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.test.ts
@@ -0,0 +1,332 @@
+import { act, renderHook, waitFor } from "@testing-library/react";
+import { hasUserEverAuthenticated } from "@web/auth/compass/state/auth.state.util";
+import { refreshUserMetadata } from "@web/auth/compass/user/util/user-metadata.util";
+import { useConnectGoogle } from "@web/auth/google/hooks/useConnectGoogle/useConnectGoogle";
+import { useGoogleAuth } from "@web/auth/google/hooks/useGoogleAuth/useGoogleAuth";
+import {
+  resetGoogleSyncUIStateForTests,
+  setRepairingSyncIndicatorOverride,
+} from "@web/auth/google/state/google.sync.state";
+import type * as GoogleAuthUtil from "@web/auth/google/util/google.auth.util";
+import { syncPendingLocalEvents } from "@web/auth/google/util/google.auth.util";
+import { AuthApi } from "@web/common/apis/auth.api";
+import { SyncApi } from "@web/common/apis/sync.api";
+import { showErrorToast } from "@web/common/utils/toast/error-toast.util";
+import {
+  selectGoogleConnectionState,
+  selectUserMetadataStatus,
+} from "@web/ducks/auth/selectors/user-metadata.selectors";
+import { triggerFetch } from "@web/ducks/events/slices/sync.slice";
+import { settingsSlice } from "@web/ducks/settings/slices/settings.slice";
+import { useAppDispatch, useAppSelector } from "@web/store/store.hooks";
+
+jest.mock("@web/auth/google/hooks/useGoogleAuth/useGoogleAuth");
+jest.mock("@web/auth/google/util/google.auth.util", () => ({
+  ...jest.requireActual<typeof GoogleAuthUtil>(
+    "@web/auth/google/util/google.auth.util",
+  ),
+  syncPendingLocalEvents: jest.fn(),
+}));
+jest.mock("@web/auth/compass/user/util/user-metadata.util");
+jest.mock("@web/auth/compass/state/auth.state.util");
+jest.mock("@web/common/apis/auth.api");
+jest.mock("@web/common/apis/sync.api");
+jest.mock("@web/common/utils/toast/error-toast.util");
+jest.mock("@web/store/store.hooks");
+
+const mockUseGoogleAuth = useGoogleAuth as jest.MockedFunction<
+  typeof useGoogleAuth
+>;
+const mockSyncPendingLocalEvents =
+  syncPendingLocalEvents as jest.MockedFunction<typeof syncPendingLocalEvents>;
+const mockShowErrorToast = showErrorToast as jest.MockedFunction<
+  typeof showErrorToast
+>;
+const mockUseAppDispatch = useAppDispatch as jest.MockedFunction<
+  typeof useAppDispatch
+>;
+const mockUseAppSelector = useAppSelector as jest.MockedFunction<
+  typeof useAppSelector
+>;
+const mockHasUserEverAuthenticated =
+  hasUserEverAuthenticated as jest.MockedFunction<
+    typeof hasUserEverAuthenticated
+  >;
+const mockAuthApi = AuthApi as jest.Mocked<typeof AuthApi>;
+const mockSyncApi = SyncApi as jest.Mocked<typeof SyncApi>;
+const mockRefreshUserMetadata = refreshUserMetadata as jest.MockedFunction<
+  typeof refreshUserMetadata
+>;
+
+const getUseGoogleAuthArg = (): NonNullable<
+  Parameters<typeof useGoogleAuth>[0]
+> => {
+  const firstCall = mockUseGoogleAuth.mock.calls.at(0);
+
+  if (!firstCall) {
+    throw new Error("Expected useGoogleAuth to be called");
+  }
+
+  return firstCall[0] ?? {};
+};
+
+describe("useConnectGoogle", () => {
+  const mockDispatch = jest.fn();
+  const mockLogin = jest.fn();
+
+  const setSelectorState = ({
+    connectionState = "NOT_CONNECTED",
+    userMetadataStatus = "loading",
+  }: {
+    connectionState?:
+      | "ATTENTION"
+      | "HEALTHY"
+      | "IMPORTING"
+      | "NOT_CONNECTED"
+      | "RECONNECT_REQUIRED";
+    userMetadataStatus?: "idle" | "loaded" | "loading";
+  } = {}) => {
+    mockUseAppSelector.mockImplementation((selector) => {
+      if (selector === selectGoogleConnectionState) {
+        return connectionState;
+      }
+
+      if (selector === selectUserMetadataStatus) {
+        return userMetadataStatus;
+      }
+
+      return undefined;
+    });
+  };
+
+  beforeEach(() => {
+    jest.clearAllMocks();
+    resetGoogleSyncUIStateForTests();
+    mockUseAppDispatch.mockReturnValue(mockDispatch);
+    mockUseGoogleAuth.mockReturnValue({
+      login: mockLogin,
+      data: null,
+      loading: false,
+    });
+    mockAuthApi.connectGoogle.mockResolvedValue({ status: "OK" });
+    mockSyncApi.importGCal.mockResolvedValue(undefined);
+    mockHasUserEverAuthenticated.mockReturnValue(true);
+    mockRefreshUserMetadata.mockResolvedValue();
+    mockSyncPendingLocalEvents.mockResolvedValue(true);
+    setSelectorState();
+  });
+
+  it("returns checking state when metadata is still loading", () => {
+    const { result } = renderHook(() => useConnectGoogle());
+
+    expect(result.current.commandAction.label).toBe(
+      "Checking Google Calendar…",
+    );
+    expect(result.current.commandAction.isDisabled).toBe(true);
+    expect(result.current.sidebarStatus.tooltip).toBe(
+      "Checking Google Calendar status…",
+    );
+  });
+
+  it("returns connect state when metadata is loaded and Google is not connected", () => {
+    setSelectorState({
+      connectionState: "NOT_CONNECTED",
+      userMetadataStatus: "loaded",
+    });
+
+    const { result } = renderHook(() => useConnectGoogle());
+
+    expect(result.current.commandAction.label).toBe("Connect Google Calendar");
+    expect(result.current.commandAction.isDisabled).toBe(false);
+    expect(result.current.sidebarStatus.tooltip).toBe(
+      "Google Calendar not connected. Click to connect.",
+    );
+  });
+
+  it("returns connected state when metadata is healthy", () => {
+    setSelectorState({
+      connectionState: "HEALTHY",
+      userMetadataStatus: "loaded",
+    });
+
+    const { result } = renderHook(() => useConnectGoogle());
+
+    expect(result.current.commandAction.label).toBe(
+      "Google Calendar Connected",
+    );
+    expect(result.current.commandAction.isDisabled).toBe(true);
+  });
+
+  it("shows repairing state from the local repair store", () => {
+    setRepairingSyncIndicatorOverride();
+    setSelectorState({
+      connectionState: "ATTENTION",
+      userMetadataStatus: "loaded",
+    });
+
+    const { result } = renderHook(() => useConnectGoogle());
+
+    expect(result.current.state).toBe("repairing");
+    expect(result.current.commandAction.label).toBe(
+      "Repairing Google Calendar…",
+    );
+    expect(result.current.isRepairing).toBe(true);
+  });
+
+  it("starts a forced repair directly and moves the UI into repairing", async () => {
+    setSelectorState({
+      connectionState: "ATTENTION",
+      userMetadataStatus: "loaded",
+    });
+
+    const { result } = renderHook(() => useConnectGoogle());
+
+    act(() => {
+      result.current.commandAction.onSelect?.();
+    });
+
+    expect(mockDispatch).toHaveBeenCalledWith(
+      settingsSlice.actions.closeCmdPalette(),
+    );
+    await waitFor(() => {
+      expect(mockSyncApi.importGCal).toHaveBeenCalledWith({ force: true });
+      expect(result.current.state).toBe("repairing");
+    });
+  });
+
+  it("clears the repair flag and shows a toast if repair start fails", async () => {
+    mockSyncApi.importGCal.mockRejectedValueOnce(new Error("boom"));
+    setSelectorState({
+      connectionState: "ATTENTION",
+      userMetadataStatus: "loaded",
+    });
+
+    const { result } = renderHook(() => useConnectGoogle());
+
+    act(() => {
+      result.current.commandAction.onSelect?.();
+    });
+
+    await waitFor(() => {
+      expect(mockShowErrorToast).toHaveBeenCalledWith(
+        "Google Calendar repair failed. Please try again.",
+        expect.anything(),
+      );
+      expect(result.current.state).toBe("ATTENTION");
+    });
+  });
+
+  it("connects Google through the backend endpoint and refreshes metadata", async () => {
+    setSelectorState({
+      connectionState: "ATTENTION",
+      userMetadataStatus: "loaded",
+    });
+
+    renderHook(() => useConnectGoogle());
+
+    const useGoogleAuthArg = getUseGoogleAuthArg();
+    if (!useGoogleAuthArg?.onSuccess) {
+      throw new Error("Expected useGoogleAuth to receive an onSuccess handler");
+    }
+
+    const payload = {
+      clientType: "web" as const,
+      thirdPartyId: "google" as const,
+      redirectURIInfo: {
+        redirectURIOnProviderDashboard: window.location.origin,
+        redirectURIQueryParams: {
+          code: "auth-code",
+          scope: "scope",
+          state: "state",
+        },
+      },
+    };
+
+    await act(async () => {
+      await useGoogleAuthArg.onSuccess(payload);
+    });
+
+    expect(mockSyncPendingLocalEvents).toHaveBeenCalledTimes(1);
+    expect(mockAuthApi.connectGoogle).toHaveBeenCalledWith(payload);
+    expect(mockRefreshUserMetadata).toHaveBeenCalledTimes(1);
+    expect(mockDispatch).toHaveBeenCalledWith(triggerFetch());
+    expect(mockSyncApi.importGCal).not.toHaveBeenCalled();
+  });
+
+  it("shows syncing UI immediately after Google auth succeeds", async () => {
+    setSelectorState({
+      connectionState: "ATTENTION",
+      userMetadataStatus: "loaded",
+    });
+
+    const { result } = renderHook(() => useConnectGoogle());
+    const useGoogleAuthArg = getUseGoogleAuthArg();
+    if (!useGoogleAuthArg?.onSuccess) {
+      throw new Error("Expected useGoogleAuth to receive an onSuccess handler");
+    }
+
+    const payload = {
+      clientType: "web" as const,
+      thirdPartyId: "google" as const,
+      redirectURIInfo: {
+        redirectURIOnProviderDashboard: window.location.origin,
+        redirectURIQueryParams: {
+          code: "auth-code",
+          scope: "scope",
+          state: "state",
+        },
+      },
+    };
+
+    await act(async () => {
+      await useGoogleAuthArg.onSuccess(payload);
+    });
+
+    expect(result.current.state).toBe("IMPORTING");
+    expect(result.current.commandAction.label).toBe("Syncing Google Calendar…");
+  });
+
+  it("shows the server message when Google connect fails", async () => {
+    setSelectorState({
+      connectionState: "NOT_CONNECTED",
+      userMetadataStatus: "loaded",
+    });
+    mockAuthApi.connectGoogle.mockRejectedValueOnce({
+      isAxiosError: true,
+      response: {
+        data: {
+          code: "GOOGLE_ACCOUNT_ALREADY_CONNECTED",
+          message:
+            "Google account is already connected to another Compass user",
+        },
+      },
+    } as never);
+
+    renderHook(() => useConnectGoogle());
+    const useGoogleAuthArg = getUseGoogleAuthArg();
+    if (!useGoogleAuthArg?.onSuccess) {
+      throw new Error("Expected useGoogleAuth to receive an onSuccess handler");
+    }
+
+    const payload = {
+      clientType: "web" as const,
+      thirdPartyId: "google" as const,
+      redirectURIInfo: {
+        redirectURIOnProviderDashboard: window.location.origin,
+        redirectURIQueryParams: {
+          code: "auth-code",
+          scope: "scope",
+          state: "state",
+        },
+      },
+    };
+
+    await expect(useGoogleAuthArg.onSuccess(payload)).resolves.toBe(false);
+
+    expect(mockShowErrorToast).toHaveBeenCalledWith(
+      "Google account is already connected to another Compass user",
+    );
+    expect(mockRefreshUserMetadata).not.toHaveBeenCalled();
+    expect(mockDispatch).not.toHaveBeenCalledWith(triggerFetch());
+  });
+});
diff --git a/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.ts b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.ts
similarity index 61%
rename from packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.ts
rename to packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.ts
index 3b4c8a439..164b412c0 100644
--- a/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.ts
+++ b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.ts
@@ -1,11 +1,18 @@
 import { type AxiosError, isAxiosError } from "axios";
-import { useCallback } from "react";
+import { useCallback, useSyncExternalStore } from "react";
 import { GOOGLE_REVOKED } from "@core/constants/sse.constants";
 import { type GoogleConnectionState } from "@core/types/user.types";
-import { syncPendingLocalEvents } from "@web/auth/google/google.auth.util";
-import { useGoogleAuth } from "@web/auth/hooks/google/useGoogleAuth/useGoogleAuth";
-import { refreshUserMetadata } from "@web/auth/session/user-metadata.util";
-import { hasUserEverAuthenticated } from "@web/auth/state/auth.state.util";
+import { hasUserEverAuthenticated } from "@web/auth/compass/state/auth.state.util";
+import { refreshUserMetadata } from "@web/auth/compass/user/util/user-metadata.util";
+import { useGoogleAuth } from "@web/auth/google/hooks/useGoogleAuth/useGoogleAuth";
+import {
+  clearGoogleSyncIndicatorOverride,
+  getGoogleSyncIndicatorOverride,
+  setRepairingSyncIndicatorOverride,
+  setSyncingSyncIndicatorOverride,
+  subscribeToGoogleSyncUIState,
+} from "@web/auth/google/state/google.sync.state";
+import { syncPendingLocalEvents } from "@web/auth/google/util/google.auth.util";
 import { AuthApi } from "@web/common/apis/auth.api";
 import {
   getApiErrorCode,
@@ -19,21 +26,24 @@ import {
   selectUserMetadataStatus,
 } from "@web/ducks/auth/selectors/user-metadata.selectors";
 import type { UserMetadataStatus } from "@web/ducks/auth/slices/user-metadata.slice";
-import { selectImportGCalState } from "@web/ducks/events/selectors/sync.selector";
-import {
-  importGCalSlice,
-  triggerFetch,
-} from "@web/ducks/events/slices/sync.slice";
+import { triggerFetch } from "@web/ducks/events/slices/sync.slice";
 import { settingsSlice } from "@web/ducks/settings/slices/settings.slice";
 import type { RootState } from "@web/store";
 import { useAppDispatch, useAppSelector } from "@web/store/store.hooks";
-import { type GoogleUiState } from "./useConnectGoogle.types";
+import {
+  type GoogleUiState,
+  type UseConnectGoogleResult,
+} from "./useConnectGoogle.types";
 import {
   buildGoogleConnectRequest,
   getGoogleConnectionConfig,
 } from "./useConnectGoogle.util";
 
-export const useConnectGoogle = () => {
+// Merges Redux-derived Google connection state with transient UI overrides from
+// google.sync.ui.state.ts; the override is read via useSyncExternalStore so React
+// stays aligned with that external store (see comments there).
+
+export const useConnectGoogle = (): UseConnectGoogleResult => {
   const dispatch = useAppDispatch();
   const connectionState = useAppSelector(
     selectGoogleConnectionState as (state: RootState) => GoogleConnectionState,
@@ -41,14 +51,14 @@ export const useConnectGoogle = () => {
   const userMetadataStatus = useAppSelector(
     selectUserMetadataStatus as (state: RootState) => UserMetadataStatus,
   );
-  const { isRepairing } = useAppSelector(
-    selectImportGCalState as (state: RootState) => {
-      isRepairing: boolean;
-    },
+  const syncIndicator = useSyncExternalStore(
+    subscribeToGoogleSyncUIState,
+    getGoogleSyncIndicatorOverride,
+    getGoogleSyncIndicatorOverride,
   );
   const { login } = useGoogleAuth({
     onSuccess: async (data) => {
-      const didSyncLocalEvents = await syncPendingLocalEvents(dispatch);
+      const didSyncLocalEvents = await syncPendingLocalEvents();
       if (!didSyncLocalEvents) {
         return false;
       }
@@ -70,6 +80,8 @@ export const useConnectGoogle = () => {
 
         throw error;
       }
+
+      setSyncingSyncIndicatorOverride();
       await refreshUserMetadata();
       dispatch(triggerFetch());
     },
@@ -82,32 +94,28 @@ export const useConnectGoogle = () => {
   }, [dispatch, login]);
 
   const onRepairGoogle = useCallback(() => {
-    dispatch(settingsSlice.actions.closeCmdPalette());
-    const run = async () => {
-      dispatch(importGCalSlice.actions.clearImportResults(undefined));
-      dispatch(importGCalSlice.actions.startRepair());
+    const startRepair = async () => {
+      dispatch(settingsSlice.actions.closeCmdPalette());
+      setRepairingSyncIndicatorOverride();
+
       try {
         await SyncApi.importGCal({ force: true });
       } catch (error) {
-        dispatch(importGCalSlice.actions.stopRepair());
-
+        clearGoogleSyncIndicatorOverride();
         const isGoogleRevoked =
           getApiErrorCode(error as AxiosError) === GOOGLE_REVOKED;
+
         if (isGoogleRevoked) {
           return;
         }
 
-        dispatch(
-          importGCalSlice.actions.setImportError(
-            "Google Calendar repair failed. Please try again.",
-          ),
-        );
         showErrorToast("Google Calendar repair failed. Please try again.", {
           toastId: GOOGLE_REPAIR_FAILED_TOAST_ID,
         });
       }
     };
-    void run();
+
+    void startRepair();
   }, [dispatch]);
 
   // "checking" is a UI-only state until we have loaded metadata from the server.
@@ -116,11 +124,18 @@ export const useConnectGoogle = () => {
   const isCheckingStatus =
     hasUserEverAuthenticated() && userMetadataStatus !== "loaded";
 
-  const state: GoogleUiState = isRepairing
-    ? "repairing"
-    : isCheckingStatus
-      ? "checking"
-      : connectionState;
+  const state: GoogleUiState =
+    syncIndicator === "repairing"
+      ? "repairing"
+      : syncIndicator === "syncing"
+        ? "IMPORTING"
+        : isCheckingStatus
+          ? "checking"
+          : connectionState;
 
-  return getGoogleConnectionConfig(state, onOpenGoogleAuth, onRepairGoogle);
+  return {
+    ...getGoogleConnectionConfig(state, onOpenGoogleAuth, onRepairGoogle),
+    isRepairing: state === "repairing",
+    state,
+  };
 };
diff --git a/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.types.ts b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.types.ts
similarity index 60%
rename from packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.types.ts
rename to packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.types.ts
index 05de13601..7e22854eb 100644
--- a/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.types.ts
+++ b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.types.ts
@@ -1,10 +1,11 @@
 import { type GoogleConnectionState } from "@core/types/user.types";
-import { type ConnectionStatusIcon } from "@web/common/types/icon.types";
 
 export type GoogleUiState = "checking" | "repairing" | GoogleConnectionState;
 
 export type CommandActionIcon = "CloudArrowUpIcon";
 
+export type IconColor = "muted" | "warning" | "error";
+
 export type GoogleUiConfig = {
   commandAction: {
     label: string;
@@ -13,10 +14,21 @@ export type GoogleUiConfig = {
     onSelect?: () => void;
   };
   sidebarStatus: {
-    icon: ConnectionStatusIcon;
     tooltip: string;
     tone?: "default" | "warning";
     isDisabled: boolean;
+    iconColor?: IconColor;
+    dialog?: {
+      title: string;
+      description: string;
+      repairLabel: string;
+      onRepair: () => void;
+    };
     onSelect?: () => void;
   };
 };
+
+export type UseConnectGoogleResult = GoogleUiConfig & {
+  isRepairing: boolean;
+  state: GoogleUiState;
+};
diff --git a/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.util.ts b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.util.ts
similarity index 79%
rename from packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.util.ts
rename to packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.util.ts
index 507591152..1d8288707 100644
--- a/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.util.ts
+++ b/packages/web/src/auth/google/hooks/useConnectGoogle/useConnectGoogle.util.ts
@@ -29,7 +29,6 @@ export const getGoogleConnectionConfig = (
           isDisabled: true,
         },
         sidebarStatus: {
-          icon: "SpinnerIcon",
           tooltip: "Checking Google Calendar status…",
           tone: "default",
           isDisabled: true,
@@ -43,10 +42,17 @@ export const getGoogleConnectionConfig = (
           isDisabled: true,
         },
         sidebarStatus: {
-          icon: "SpinnerIcon",
+          iconColor: "warning",
           tooltip: "Repairing Google Calendar in the background.",
           tone: "warning",
           isDisabled: true,
+          dialog: {
+            title: "Calendar sync needs repair",
+            description:
+              "Your Google Calendar has run into a sync issue. Repairing will re-import your recent events to make sure everything is up to date.",
+            repairLabel: "Repair",
+            onRepair: onRepairGoogle,
+          },
         },
       };
     case "NOT_CONNECTED":
@@ -58,7 +64,7 @@ export const getGoogleConnectionConfig = (
           onSelect: onConnectGoogle,
         },
         sidebarStatus: {
-          icon: "CloudArrowUpIcon",
+          iconColor: "muted",
           tooltip: "Google Calendar not connected. Click to connect.",
           tone: "default",
           isDisabled: false,
@@ -74,7 +80,7 @@ export const getGoogleConnectionConfig = (
           onSelect: onConnectGoogle,
         },
         sidebarStatus: {
-          icon: "LinkBreakIcon",
+          iconColor: "error",
           tooltip: "Google Calendar needs reconnecting. Click to reconnect.",
           tone: "default",
           isDisabled: false,
@@ -89,7 +95,6 @@ export const getGoogleConnectionConfig = (
           isDisabled: true,
         },
         sidebarStatus: {
-          icon: "SpinnerIcon",
           tooltip: "Google Calendar is syncing in the background.",
           tone: "default",
           isDisabled: true,
@@ -104,11 +109,17 @@ export const getGoogleConnectionConfig = (
           onSelect: onRepairGoogle,
         },
         sidebarStatus: {
-          icon: "CloudWarningIcon",
+          iconColor: "warning",
           tooltip: "Google Calendar needs repair. Click to repair.",
           tone: "warning",
           isDisabled: false,
-          onSelect: onRepairGoogle,
+          dialog: {
+            title: "Calendar sync needs repair",
+            description:
+              "Your Google Calendar has run into a sync issue. Repairing will re-import your recent events to make sure everything is up to date.",
+            repairLabel: "Repair",
+            onRepair: onRepairGoogle,
+          },
         },
       };
     case "HEALTHY":
@@ -119,7 +130,7 @@ export const getGoogleConnectionConfig = (
           isDisabled: true,
         },
         sidebarStatus: {
-          icon: "LinkIcon",
+          iconColor: "muted",
           tooltip: "Google Calendar connected.",
           tone: "default",
           isDisabled: true,
diff --git a/packages/web/src/auth/hooks/google/useGoogleAuth/useGoogleAuth.test.ts b/packages/web/src/auth/google/hooks/useGoogleAuth/useGoogleAuth.test.ts
similarity index 93%
rename from packages/web/src/auth/hooks/google/useGoogleAuth/useGoogleAuth.test.ts
rename to packages/web/src/auth/google/hooks/useGoogleAuth/useGoogleAuth.test.ts
index adf2f389c..da11ae2de 100644
--- a/packages/web/src/auth/hooks/google/useGoogleAuth/useGoogleAuth.test.ts
+++ b/packages/web/src/auth/google/hooks/useGoogleAuth/useGoogleAuth.test.ts
@@ -1,23 +1,23 @@
 import { toast } from "react-toastify";
 import { renderHook, waitFor } from "@testing-library/react";
+import { useSession } from "@web/auth/compass/session/useSession";
+import { markUserAsAuthenticated } from "@web/auth/compass/state/auth.state.util";
+import { refreshUserMetadata } from "@web/auth/compass/user/util/user-metadata.util";
+import { useGoogleAuth } from "@web/auth/google/hooks/useGoogleAuth/useGoogleAuth";
+import { useGoogleLogin } from "@web/auth/google/hooks/useGoogleLogin/useGoogleLogin";
 import {
   authenticate,
   syncLocalEvents,
-} from "@web/auth/google/google.auth.util";
-import { useGoogleAuth } from "@web/auth/hooks/google/useGoogleAuth/useGoogleAuth";
-import { useGoogleLogin } from "@web/auth/hooks/google/useGoogleLogin/useGoogleLogin";
-import { useSession } from "@web/auth/hooks/session/useSession";
-import { refreshUserMetadata } from "@web/auth/session/user-metadata.util";
-import { markUserAsAuthenticated } from "@web/auth/state/auth.state.util";
+} from "@web/auth/google/util/google.auth.util";
 import { useAppDispatch } from "@web/store/store.hooks";
 import { type GoogleAuthConfig } from "../googe.auth.types";
 
 // Mock dependencies
-jest.mock("@web/auth/google/google.auth.util");
-jest.mock("@web/auth/hooks/session/useSession");
-jest.mock("@web/auth/session/user-metadata.util");
-jest.mock("@web/auth/hooks/google/useGoogleLogin/useGoogleLogin");
-jest.mock("@web/auth/state/auth.state.util");
+jest.mock("@web/auth/google/util/google.auth.util");
+jest.mock("@web/auth/compass/session/useSession");
+jest.mock("@web/auth/compass/user/util/user-metadata.util");
+jest.mock("@web/auth/google/hooks/useGoogleLogin/useGoogleLogin");
+jest.mock("@web/auth/compass/state/auth.state.util");
 jest.mock("@web/store/store.hooks", () => ({
   useAppDispatch: jest.fn(),
 }));
@@ -160,7 +160,7 @@ describe("useGoogleAuth", () => {
   });
 
   describe("onStart callback", () => {
-    it("shows overlay immediately when login starts and clears prior import results", () => {
+    it("shows overlay immediately when login starts", () => {
       mockUseGoogleLogin.mockReturnValue({
         login: mockLogin,
         loading: false,
@@ -175,11 +175,6 @@ describe("useGoogleAuth", () => {
       expect(mockDispatchFn).toHaveBeenCalledWith(
         expect.objectContaining({ type: "auth/startAuthenticating" }),
       );
-      expect(mockDispatchFn).toHaveBeenCalledWith(
-        expect.objectContaining({
-          type: "async/importGCal/clearImportResults",
-        }),
-      );
       expect(mockToast.dismiss).toHaveBeenCalledWith("session-expired-api");
     });
   });
diff --git a/packages/web/src/auth/hooks/google/useGoogleAuth/useGoogleAuth.ts b/packages/web/src/auth/google/hooks/useGoogleAuth/useGoogleAuth.ts
similarity index 86%
rename from packages/web/src/auth/hooks/google/useGoogleAuth/useGoogleAuth.ts
rename to packages/web/src/auth/google/hooks/useGoogleAuth/useGoogleAuth.ts
index 11f620465..e653a0158 100644
--- a/packages/web/src/auth/hooks/google/useGoogleAuth/useGoogleAuth.ts
+++ b/packages/web/src/auth/google/hooks/useGoogleAuth/useGoogleAuth.ts
@@ -1,8 +1,8 @@
 import { toast } from "react-toastify";
-import { isGooglePopupClosedError } from "@web/auth/google/google-oauth-error.util";
-import { authenticate } from "@web/auth/google/google.auth.util";
-import { useCompleteAuthentication } from "@web/auth/hooks/compass/useCompleteAuthentication";
-import { useGoogleAuthWithOverlay } from "@web/auth/hooks/google/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay";
+import { useCompleteAuthentication } from "@web/auth/compass/hooks/useCompleteAuthentication";
+import { useGoogleAuthWithOverlay } from "@web/auth/google/hooks/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay";
+import { authenticate } from "@web/auth/google/util/google.auth.util";
+import { isGooglePopupClosedError } from "@web/auth/google/util/google.oauth.error.util";
 import { toastDefaultOptions } from "@web/common/constants/toast.constants";
 import {
   SESSION_EXPIRED_TOAST_ID,
@@ -14,7 +14,6 @@ import {
   resetAuth,
   startAuthenticating,
 } from "@web/ducks/auth/slices/auth.slice";
-import { importGCalSlice } from "@web/ducks/events/slices/sync.slice";
 import { type AppDispatch } from "@web/store";
 import { useAppDispatch } from "@web/store/store.hooks";
 import { type GoogleAuthConfig } from "../googe.auth.types";
@@ -52,7 +51,6 @@ export function useGoogleAuth(
     onStart: () => {
       dismissErrorToast(SESSION_EXPIRED_TOAST_ID);
       dispatch(startAuthenticating());
-      dispatch(importGCalSlice.actions.clearImportResults(undefined));
     },
     onSuccess: async (data) => {
       if (onSuccess) {
diff --git a/packages/web/src/auth/hooks/google/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.test.ts b/packages/web/src/auth/google/hooks/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.test.ts
similarity index 94%
rename from packages/web/src/auth/hooks/google/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.test.ts
rename to packages/web/src/auth/google/hooks/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.test.ts
index b6a7864f4..a0db5d1a4 100644
--- a/packages/web/src/auth/hooks/google/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.test.ts
+++ b/packages/web/src/auth/google/hooks/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.test.ts
@@ -1,9 +1,9 @@
 import { renderHook, waitFor } from "@testing-library/react";
-import { useGoogleAuthWithOverlay } from "@web/auth/hooks/google/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay";
-import { useGoogleLogin } from "@web/auth/hooks/google/useGoogleLogin/useGoogleLogin";
+import { useGoogleAuthWithOverlay } from "@web/auth/google/hooks/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay";
+import { useGoogleLogin } from "@web/auth/google/hooks/useGoogleLogin/useGoogleLogin";
 import { type GoogleAuthConfig } from "../googe.auth.types";
 
-jest.mock("@web/auth/hooks/google/useGoogleLogin/useGoogleLogin");
+jest.mock("@web/auth/google/hooks/useGoogleLogin/useGoogleLogin");
 
 const mockUseGoogleLogin = useGoogleLogin as jest.MockedFunction<
   typeof useGoogleLogin
diff --git a/packages/web/src/auth/hooks/google/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.ts b/packages/web/src/auth/google/hooks/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.ts
similarity index 94%
rename from packages/web/src/auth/hooks/google/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.ts
rename to packages/web/src/auth/google/hooks/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.ts
index 0018394ee..185eeffcb 100644
--- a/packages/web/src/auth/hooks/google/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.ts
+++ b/packages/web/src/auth/google/hooks/useGoogleAuthWithOverlay/useGoogleAuthWithOverlay.ts
@@ -1,5 +1,5 @@
 import { useCallback } from "react";
-import { useGoogleLogin } from "@web/auth/hooks/google/useGoogleLogin/useGoogleLogin";
+import { useGoogleLogin } from "@web/auth/google/hooks/useGoogleLogin/useGoogleLogin";
 import { type GoogleAuthConfig } from "../googe.auth.types";
 
 interface UseGoogleAuthWithOverlayOptions {
diff --git a/packages/web/src/auth/hooks/google/useGoogleLogin/useGoogleLogin.ts b/packages/web/src/auth/google/hooks/useGoogleLogin/useGoogleLogin.ts
similarity index 96%
rename from packages/web/src/auth/hooks/google/useGoogleLogin/useGoogleLogin.ts
rename to packages/web/src/auth/google/hooks/useGoogleLogin/useGoogleLogin.ts
index e45696833..15f75cb10 100644
--- a/packages/web/src/auth/hooks/google/useGoogleLogin/useGoogleLogin.ts
+++ b/packages/web/src/auth/google/hooks/useGoogleLogin/useGoogleLogin.ts
@@ -1,7 +1,7 @@
 import { useCallback, useRef, useState } from "react";
 import { v4 as uuidv4 } from "uuid";
 import { useGoogleLogin as useGoogleLoginBase } from "@react-oauth/google";
-import { isGooglePopupClosedError } from "@web/auth/google/google-oauth-error.util";
+import { isGooglePopupClosedError } from "@web/auth/google/util/google.oauth.error.util";
 import { type GoogleAuthConfig } from "../googe.auth.types";
 
 const SCOPES_REQUIRED = [
diff --git a/packages/web/src/auth/google/google.auth.state.test.ts b/packages/web/src/auth/google/state/google.auth.state.test.ts
similarity index 100%
rename from packages/web/src/auth/google/google.auth.state.test.ts
rename to packages/web/src/auth/google/state/google.auth.state.test.ts
diff --git a/packages/web/src/auth/google/google.auth.state.ts b/packages/web/src/auth/google/state/google.auth.state.ts
similarity index 100%
rename from packages/web/src/auth/google/google.auth.state.ts
rename to packages/web/src/auth/google/state/google.auth.state.ts
diff --git a/packages/web/src/auth/google/state/google.sync.state.ts b/packages/web/src/auth/google/state/google.sync.state.ts
new file mode 100644
index 000000000..f90260b8a
--- /dev/null
+++ b/packages/web/src/auth/google/state/google.sync.state.ts
@@ -0,0 +1,50 @@
+// Transient Google sync UI overrides (e.g. repairing, post-connect syncing) live outside
+// Redux so auth/sync helpers can update them from async callbacks without dispatch.
+// This module is a minimal external store (mutable snapshot + listener set). Consumers
+// subscribe with useSyncExternalStore(subscribeToGoogleSyncUIState, getGoogleSyncIndicatorOverride, …).
+
+const googleSyncUIListeners = new Set<() => void>();
+
+type SyncIndicator = null | "repairing" | "syncing";
+
+let gSyncIndicator: SyncIndicator = null;
+
+const emitGoogleSyncUIChange = () => {
+  googleSyncUIListeners.forEach((listener) => listener());
+};
+
+const setGoogleSyncIndicatorOverride = (nextOverride: SyncIndicator) => {
+  if (gSyncIndicator === nextOverride) {
+    return;
+  }
+
+  gSyncIndicator = nextOverride;
+  emitGoogleSyncUIChange();
+};
+
+export const clearGoogleSyncIndicatorOverride = () => {
+  setGoogleSyncIndicatorOverride(null);
+};
+
+export const getGoogleSyncIndicatorOverride = () => gSyncIndicator;
+
+export const setRepairingSyncIndicatorOverride = () => {
+  setGoogleSyncIndicatorOverride("repairing");
+};
+
+export const setSyncingSyncIndicatorOverride = () => {
+  setGoogleSyncIndicatorOverride("syncing");
+};
+
+export const resetGoogleSyncUIStateForTests = () => {
+  gSyncIndicator = null;
+  emitGoogleSyncUIChange();
+};
+
+export const subscribeToGoogleSyncUIState = (listener: () => void) => {
+  googleSyncUIListeners.add(listener);
+
+  return () => {
+    googleSyncUIListeners.delete(listener);
+  };
+};
diff --git a/packages/web/src/auth/google/google.auth.util.test.ts b/packages/web/src/auth/google/util/google.auth.util.test.ts
similarity index 89%
rename from packages/web/src/auth/google/google.auth.util.test.ts
rename to packages/web/src/auth/google/util/google.auth.util.test.ts
index 28177ae9b..6eebac566 100644
--- a/packages/web/src/auth/google/google.auth.util.test.ts
+++ b/packages/web/src/auth/google/util/google.auth.util.test.ts
@@ -3,7 +3,7 @@ import { Origin } from "@core/constants/core.constants";
 import {
   clearGoogleRevokedState,
   isGoogleRevoked,
-} from "@web/auth/google/google.auth.state";
+} from "@web/auth/google/state/google.auth.state";
 import { AuthApi } from "@web/common/apis/auth.api";
 import { GOOGLE_REVOKED_TOAST_ID } from "@web/common/constants/toast.constants";
 import { syncLocalEventsToCloud } from "@web/common/utils/sync/local-event-sync.util";
@@ -11,13 +11,10 @@ import { authSlice } from "@web/ducks/auth/slices/auth.slice";
 import { userMetadataSlice } from "@web/ducks/auth/slices/user-metadata.slice";
 import { Sync_AsyncStateContextReason } from "@web/ducks/events/context/sync.context";
 import { eventsEntitiesSlice } from "@web/ducks/events/slices/event.slice";
-import {
-  importGCalSlice,
-  triggerFetch,
-} from "@web/ducks/events/slices/sync.slice";
+import { triggerFetch } from "@web/ducks/events/slices/sync.slice";
 import { closeStream, openStream } from "@web/sse/client/sse.client";
 import { store } from "@web/store";
-import { type GoogleAuthConfig } from "../hooks/google/googe.auth.types";
+import { type GoogleAuthConfig } from "../hooks/googe.auth.types";
 import {
   LOCAL_EVENTS_SYNC_ERROR_MESSAGE,
   authenticate,
@@ -152,41 +149,33 @@ describe("google-auth.util", () => {
       jest.restoreAllMocks();
     });
 
-    it("dispatches setLocalEventsSynced when sync succeeds with events", async () => {
+    it("returns true when sync succeeds with events", async () => {
       mockSyncLocalEventsToCloud.mockResolvedValue(3);
-      const dispatch = jest.fn();
 
-      const ok = await syncPendingLocalEvents(dispatch);
+      const ok = await syncPendingLocalEvents();
 
       expect(ok).toBe(true);
-      expect(dispatch).toHaveBeenCalledWith(
-        importGCalSlice.actions.setLocalEventsSynced(3),
-      );
     });
 
-    it("does not dispatch when syncedCount is zero", async () => {
+    it("returns true when syncedCount is zero", async () => {
       mockSyncLocalEventsToCloud.mockResolvedValue(0);
-      const dispatch = jest.fn();
 
-      const ok = await syncPendingLocalEvents(dispatch);
+      const ok = await syncPendingLocalEvents();
 
       expect(ok).toBe(true);
-      expect(dispatch).not.toHaveBeenCalled();
     });
 
     it("shows toast and returns false on sync failure", async () => {
       const error = new Error("fail");
       mockSyncLocalEventsToCloud.mockRejectedValue(error);
-      const dispatch = jest.fn();
 
-      const ok = await syncPendingLocalEvents(dispatch);
+      const ok = await syncPendingLocalEvents();
 
       expect(ok).toBe(false);
       expect(toast.error).toHaveBeenCalledWith(
         LOCAL_EVENTS_SYNC_ERROR_MESSAGE,
         expect.anything(),
       );
-      expect(dispatch).not.toHaveBeenCalled();
     });
   });
 
diff --git a/packages/web/src/auth/google/google.auth.util.ts b/packages/web/src/auth/google/util/google.auth.util.ts
similarity index 83%
rename from packages/web/src/auth/google/google.auth.util.ts
rename to packages/web/src/auth/google/util/google.auth.util.ts
index 760653d22..d1b161ba5 100644
--- a/packages/web/src/auth/google/google.auth.util.ts
+++ b/packages/web/src/auth/google/util/google.auth.util.ts
@@ -1,7 +1,7 @@
 import { toast } from "react-toastify";
 import { Origin } from "@core/constants/core.constants";
 import { type Result_Auth_Compass } from "@core/types/auth.types";
-import { markGoogleAsRevoked } from "@web/auth/google/google.auth.state";
+import { markGoogleAsRevoked } from "@web/auth/google/state/google.auth.state";
 import { AuthApi } from "@web/common/apis/auth.api";
 import {
   GOOGLE_REVOKED_TOAST_ID,
@@ -12,13 +12,10 @@ import { authSlice } from "@web/ducks/auth/slices/auth.slice";
 import { userMetadataSlice } from "@web/ducks/auth/slices/user-metadata.slice";
 import { Sync_AsyncStateContextReason } from "@web/ducks/events/context/sync.context";
 import { eventsEntitiesSlice } from "@web/ducks/events/slices/event.slice";
-import {
-  importGCalSlice,
-  triggerFetch,
-} from "@web/ducks/events/slices/sync.slice";
+import { triggerFetch } from "@web/ducks/events/slices/sync.slice";
 import { closeStream, openStream } from "@web/sse/client/sse.client";
-import { type AppDispatch, store } from "@web/store";
-import { type GoogleAuthConfig } from "../hooks/google/googe.auth.types";
+import { store } from "@web/store";
+import { type GoogleAuthConfig } from "../hooks/googe.auth.types";
 
 export interface AuthenticateResult {
   success: boolean;
@@ -98,12 +95,10 @@ export async function syncLocalEvents(): Promise<SyncLocalEventsResult> {
 }
 
 /**
- * Runs {@link syncLocalEvents}, surfaces failures with a toast, and records
- * synced counts in Redux when migration succeeds. Returns whether sync succeeded.
+ * Runs {@link syncLocalEvents}, surfaces failures with a toast, and returns
+ * whether sync succeeded.
  */
-export async function syncPendingLocalEvents(
-  dispatch: AppDispatch,
-): Promise<boolean> {
+export async function syncPendingLocalEvents(): Promise<boolean> {
   const syncResult = await syncLocalEvents();
 
   if (!syncResult.success) {
@@ -111,11 +106,5 @@ export async function syncPendingLocalEvents(
     return false;
   }
 
-  if (syncResult.syncedCount > 0) {
-    dispatch(
-      importGCalSlice.actions.setLocalEventsSynced(syncResult.syncedCount),
-    );
-  }
-
   return true;
 }
diff --git a/packages/web/src/auth/google/google-oauth-error.util.test.ts b/packages/web/src/auth/google/util/google.oauth.error.util.test.ts
similarity index 86%
rename from packages/web/src/auth/google/google-oauth-error.util.test.ts
rename to packages/web/src/auth/google/util/google.oauth.error.util.test.ts
index 46ea8958c..4ac48a4c4 100644
--- a/packages/web/src/auth/google/google-oauth-error.util.test.ts
+++ b/packages/web/src/auth/google/util/google.oauth.error.util.test.ts
@@ -1,4 +1,4 @@
-import { isGooglePopupClosedError } from "@web/auth/google/google-oauth-error.util";
+import { isGooglePopupClosedError } from "@web/auth/google/util/google.oauth.error.util";
 
 describe("isGooglePopupClosedError", () => {
   it("returns true for non-oauth popup_closed type", () => {
diff --git a/packages/web/src/auth/google/google-oauth-error.util.ts b/packages/web/src/auth/google/util/google.oauth.error.util.ts
similarity index 100%
rename from packages/web/src/auth/google/google-oauth-error.util.ts
rename to packages/web/src/auth/google/util/google.oauth.error.util.ts
diff --git a/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.test.ts b/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.test.ts
deleted file mode 100644
index b41ce3a93..000000000
--- a/packages/web/src/auth/hooks/google/useConnectGoogle/useConnectGoogle.test.ts
+++ /dev/null
@@ -1,629 +0,0 @@
-import { toast } from "react-toastify";
-import { renderHook, waitFor } from "@testing-library/react";
-import type * as GoogleAuthUtil from "@web/auth/google/google.auth.util";
-import { syncPendingLocalEvents } from "@web/auth/google/google.auth.util";
-import { useConnectGoogle } from "@web/auth/hooks/google/useConnectGoogle/useConnectGoogle";
-import { useGoogleAuth } from "@web/auth/hooks/google/useGoogleAuth/useGoogleAuth";
-import { refreshUserMetadata } from "@web/auth/session/user-metadata.util";
-import { hasUserEverAuthenticated } from "@web/auth/state/auth.state.util";
-import { AuthApi } from "@web/common/apis/auth.api";
-import { SyncApi } from "@web/common/apis/sync.api";
-import { showErrorToast } from "@web/common/utils/toast/error-toast.util";
-import {
-  selectGoogleConnectionState,
-  selectUserMetadataStatus,
-} from "@web/ducks/auth/selectors/user-metadata.selectors";
-import { selectImportGCalState } from "@web/ducks/events/selectors/sync.selector";
-import {
-  importGCalSlice,
-  triggerFetch,
-} from "@web/ducks/events/slices/sync.slice";
-import { settingsSlice } from "@web/ducks/settings/slices/settings.slice";
-import { useAppDispatch, useAppSelector } from "@web/store/store.hooks";
-
-jest.mock("@web/auth/hooks/google/useGoogleAuth/useGoogleAuth");
-jest.mock("@web/auth/google/google.auth.util", () => ({
-  ...jest.requireActual<typeof GoogleAuthUtil>(
-    "@web/auth/google/google.auth.util",
-  ),
-  syncPendingLocalEvents: jest.fn(),
-}));
-jest.mock("@web/auth/session/user-metadata.util");
-jest.mock("@web/auth/state/auth.state.util");
-jest.mock("@web/common/apis/auth.api");
-jest.mock("@web/common/apis/sync.api");
-jest.mock("@web/common/utils/toast/error-toast.util");
-jest.mock("@web/store/store.hooks");
-jest.mock("react-toastify", () => ({
-  toast: {
-    error: jest.fn(),
-  },
-}));
-
-const mockUseGoogleAuth = useGoogleAuth as jest.MockedFunction<
-  typeof useGoogleAuth
->;
-const mockSyncPendingLocalEvents =
-  syncPendingLocalEvents as jest.MockedFunction<typeof syncPendingLocalEvents>;
-const mockShowErrorToast = showErrorToast as jest.MockedFunction<
-  typeof showErrorToast
->;
-const mockUseAppDispatch = useAppDispatch as jest.MockedFunction<
-  typeof useAppDispatch
->;
-const mockUseAppSelector = useAppSelector as jest.MockedFunction<
-  typeof useAppSelector
->;
-const mockHasUserEverAuthenticated =
-  hasUserEverAuthenticated as jest.MockedFunction<
-    typeof hasUserEverAuthenticated
-  >;
-const mockAuthApi = AuthApi as jest.Mocked<typeof AuthApi>;
-const mockRefreshUserMetadata = refreshUserMetadata as jest.MockedFunction<
-  typeof refreshUserMetadata
->;
-const mockSyncApi = SyncApi as jest.Mocked<typeof SyncApi>;
-const mockToastError = toast.error as jest.MockedFunction<typeof toast.error>;
-
-const getUseGoogleAuthArg = (): NonNullable<
-  Parameters<typeof useGoogleAuth>[0]
-> => {
-  const firstCall = mockUseGoogleAuth.mock.calls.at(0);
-
-  if (!firstCall) {
-    throw new Error("Expected useGoogleAuth to be called");
-  }
-
-  return firstCall[0] ?? {};
-};
-
-describe("useConnectGoogle", () => {
-  const mockDispatch = jest.fn();
-  const mockLogin = jest.fn();
-
-  const expectGoogleAuthConfig = () => {
-    const arg = getUseGoogleAuthArg();
-
-    expect(arg.prompt).toBe("consent");
-    expect(typeof arg.onSuccess).toBe("function");
-  };
-
-  beforeEach(() => {
-    jest.clearAllMocks();
-    jest.spyOn(console, "error").mockImplementation(() => {});
-    mockUseAppDispatch.mockReturnValue(mockDispatch);
-    mockUseGoogleAuth.mockReturnValue({
-      login: mockLogin,
-      data: null,
-      loading: false,
-    });
-    mockAuthApi.connectGoogle.mockResolvedValue({ status: "OK" });
-    mockHasUserEverAuthenticated.mockReturnValue(true);
-    mockRefreshUserMetadata.mockResolvedValue();
-    mockSyncApi.importGCal.mockResolvedValue(undefined as never);
-    mockSyncPendingLocalEvents.mockResolvedValue(true);
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "NOT_CONNECTED";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loading";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-  });
-
-  it("returns checking state when metadata is still loading", () => {
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe(
-      "Checking Google Calendar…",
-    );
-    expect(result.current.commandAction.isDisabled).toBe(true);
-    expect(result.current.sidebarStatus.icon).toBe("SpinnerIcon");
-    expect(result.current.sidebarStatus.tooltip).toBe(
-      "Checking Google Calendar status…",
-    );
-  });
-
-  it("returns checking state when metadata is idle before refresh", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "NOT_CONNECTED";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "idle";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expect(result.current.commandAction.label).toBe(
-      "Checking Google Calendar…",
-    );
-    expect(result.current.sidebarStatus.icon).toBe("SpinnerIcon");
-  });
-
-  it("returns connect state when metadata is loaded and Google is not connected", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "NOT_CONNECTED";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe("Connect Google Calendar");
-    expect(result.current.commandAction.isDisabled).toBe(false);
-    expect(result.current.sidebarStatus.icon).toBe("CloudArrowUpIcon");
-    expect(result.current.sidebarStatus.tooltip).toBe(
-      "Google Calendar not connected. Click to connect.",
-    );
-  });
-
-  it("returns connected state when metadata is healthy", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "HEALTHY";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe(
-      "Google Calendar Connected",
-    );
-    expect(result.current.commandAction.isDisabled).toBe(true);
-    expect(result.current.commandAction.onSelect).toBeUndefined();
-    expect(result.current.sidebarStatus.icon).toBe("LinkIcon");
-    expect(result.current.sidebarStatus.isDisabled).toBe(true);
-  });
-
-  it("returns reconnect state when refresh token is missing", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "RECONNECT_REQUIRED";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe(
-      "Reconnect Google Calendar",
-    );
-    expect(result.current.sidebarStatus.icon).toBe("LinkBreakIcon");
-
-    result.current.commandAction.onSelect?.();
-
-    expect(mockLogin).toHaveBeenCalled();
-    expect(mockDispatch).toHaveBeenCalledWith(
-      settingsSlice.actions.closeCmdPalette(),
-    );
-  });
-
-  it("returns syncing state while import is running", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "IMPORTING";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe("Syncing Google Calendar…");
-    expect(result.current.commandAction.isDisabled).toBe(true);
-    expect(result.current.commandAction.onSelect).toBeUndefined();
-    expect(result.current.sidebarStatus.icon).toBe("SpinnerIcon");
-    expect(result.current.sidebarStatus.isDisabled).toBe(true);
-  });
-
-  it("returns repair state when sync needs attention", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "ATTENTION";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe("Repair Google Calendar");
-    expect(result.current.commandAction.isDisabled).toBe(false);
-    expect(result.current.sidebarStatus.icon).toBe("CloudWarningIcon");
-    expect(result.current.sidebarStatus.tooltip).toBe(
-      "Google Calendar needs repair. Click to repair.",
-    );
-
-    result.current.sidebarStatus.onSelect?.();
-
-    expect(mockSyncApi.importGCal).toHaveBeenCalledWith({ force: true });
-    expect(mockDispatch).toHaveBeenCalledWith(
-      importGCalSlice.actions.clearImportResults(undefined),
-    );
-    expect(mockDispatch).toHaveBeenCalledWith(
-      importGCalSlice.actions.startRepair(),
-    );
-    expect(mockDispatch).toHaveBeenCalledWith(
-      settingsSlice.actions.closeCmdPalette(),
-    );
-
-    jest.clearAllMocks();
-
-    result.current.commandAction.onSelect?.();
-
-    expect(mockSyncApi.importGCal).toHaveBeenCalledWith({ force: true });
-    expect(mockDispatch).toHaveBeenCalledWith(
-      settingsSlice.actions.closeCmdPalette(),
-    );
-  });
-
-  it("returns repairing state while a repair is active", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "ATTENTION";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: true };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expect(result.current.commandAction.label).toBe(
-      "Repairing Google Calendar…",
-    );
-    expect(result.current.commandAction.isDisabled).toBe(true);
-    expect(result.current.sidebarStatus.icon).toBe("SpinnerIcon");
-    expect(result.current.sidebarStatus.tone).toBe("warning");
-    expect(result.current.sidebarStatus.tooltip).toBe(
-      "Repairing Google Calendar in the background.",
-    );
-  });
-
-  it("shows a toast and clears repair state when the repair request fails to start", async () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "ATTENTION";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-    mockSyncApi.importGCal.mockRejectedValueOnce(new Error("boom"));
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    result.current.commandAction.onSelect?.();
-
-    await waitFor(() =>
-      expect(mockDispatch).toHaveBeenCalledWith(
-        importGCalSlice.actions.setImportError(
-          "Google Calendar repair failed. Please try again.",
-        ),
-      ),
-    );
-    expect(mockDispatch).toHaveBeenCalledWith(
-      importGCalSlice.actions.stopRepair(),
-    );
-    expect(mockShowErrorToast).toHaveBeenCalledWith(
-      "Google Calendar repair failed. Please try again.",
-      { toastId: "google-repair-failed" },
-    );
-  });
-
-  it("shows connect state when server says not connected", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "NOT_CONNECTED";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe("Connect Google Calendar");
-    expect(result.current.commandAction.isDisabled).toBe(false);
-    expect(result.current.sidebarStatus.icon).toBe("CloudArrowUpIcon");
-    expect(result.current.sidebarStatus.isDisabled).toBe(false);
-  });
-
-  it("shows reconnect_required state from the server", () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "RECONNECT_REQUIRED";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe(
-      "Reconnect Google Calendar",
-    );
-    expect(result.current.sidebarStatus.icon).toBe("LinkBreakIcon");
-    expect(result.current.commandAction.isDisabled).toBe(false);
-  });
-
-  it("returns connect state when metadata is missing for a never-authenticated user", () => {
-    mockHasUserEverAuthenticated.mockReturnValue(false);
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "NOT_CONNECTED";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "idle";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-
-    const { result } = renderHook(() => useConnectGoogle());
-
-    expectGoogleAuthConfig();
-    expect(result.current.commandAction.label).toBe("Connect Google Calendar");
-    expect(result.current.sidebarStatus.icon).toBe("CloudArrowUpIcon");
-  });
-
-  it("connects Google through the backend endpoint and refreshes metadata", async () => {
-    renderHook(() => useConnectGoogle());
-
-    const useGoogleAuthArg = getUseGoogleAuthArg();
-    if (!useGoogleAuthArg?.onSuccess) {
-      throw new Error("Expected useGoogleAuth to receive an onSuccess handler");
-    }
-
-    const payload = {
-      clientType: "web" as const,
-      thirdPartyId: "google" as const,
-      redirectURIInfo: {
-        redirectURIOnProviderDashboard: window.location.origin,
-        redirectURIQueryParams: {
-          code: "auth-code",
-          scope: "scope",
-          state: "state",
-        },
-      },
-    };
-
-    await useGoogleAuthArg.onSuccess(payload);
-
-    expect(mockSyncPendingLocalEvents).toHaveBeenCalledTimes(1);
-    expect(mockAuthApi.connectGoogle).toHaveBeenCalledWith(payload);
-    expect(mockRefreshUserMetadata).toHaveBeenCalledTimes(1);
-    expect(mockDispatch).toHaveBeenCalledWith(triggerFetch());
-  });
-
-  it("shows the server message when Google connect fails and keeps the connect action visible", async () => {
-    mockUseAppSelector.mockImplementation((selector) => {
-      if (selector === selectGoogleConnectionState) {
-        return "NOT_CONNECTED";
-      }
-
-      if (selector === selectUserMetadataStatus) {
-        return "loaded";
-      }
-
-      if (selector === selectImportGCalState) {
-        return { isRepairing: false };
-      }
-
-      return undefined;
-    });
-    mockAuthApi.connectGoogle.mockRejectedValueOnce({
-      isAxiosError: true,
-      response: {
-        data: {
-          code: "GOOGLE_ACCOUNT_ALREADY_CONNECTED",
-          message:
-            "Google account is already connected to another Compass user",
-        },
-      },
-    } as never);
-
-    const { result } = renderHook(() => useConnectGoogle());
-    const useGoogleAuthArg = getUseGoogleAuthArg();
-    if (!useGoogleAuthArg?.onSuccess) {
-      throw new Error("Expected useGoogleAuth to receive an onSuccess handler");
-    }
-
-    const payload = {
-      clientType: "web" as const,
-      thirdPartyId: "google" as const,
-      redirectURIInfo: {
-        redirectURIOnProviderDashboard: window.location.origin,
-        redirectURIQueryParams: {
-          code: "auth-code",
-          scope: "scope",
-          state: "state",
-        },
-      },
-    };
-
-    await expect(useGoogleAuthArg.onSuccess(payload)).resolves.toBe(false);
-
-    expect(mockShowErrorToast).toHaveBeenCalledWith(
-      "Google account is already connected to another Compass user",
-    );
-    expect(mockRefreshUserMetadata).not.toHaveBeenCalled();
-    expect(mockDispatch).not.toHaveBeenCalledWith(triggerFetch());
-    expect(result.current.commandAction.label).toBe("Connect Google Calendar");
-  });
-
-  it("records synced local events before refreshing Google data", async () => {
-    mockSyncPendingLocalEvents.mockImplementation((dispatch) => {
-      dispatch(importGCalSlice.actions.setLocalEventsSynced(2));
-      return Promise.resolve(true);
-    });
-
-    renderHook(() => useConnectGoogle());
-
-    const useGoogleAuthArg = getUseGoogleAuthArg();
-    if (!useGoogleAuthArg?.onSuccess) {
-      throw new Error("Expected useGoogleAuth to receive an onSuccess handler");
-    }
-
-    const payload = {
-      clientType: "web" as const,
-      thirdPartyId: "google" as const,
-      redirectURIInfo: {
-        redirectURIOnProviderDashboard: window.location.origin,
-        redirectURIQueryParams: {
-          code: "auth-code",
-          scope: "scope",
-          state: "state",
-        },
-      },
-    };
-
-    await useGoogleAuthArg.onSuccess(payload);
-
-    expect(mockDispatch).toHaveBeenCalledWith(
-      importGCalSlice.actions.setLocalEventsSynced(2),
-    );
-    expect(mockAuthApi.connectGoogle).toHaveBeenCalledWith(payload);
-  });
-
-  it("does not connect Google when local event sync fails", async () => {
-    const { showLocalEventsSyncFailure } = jest.requireActual<
-      typeof GoogleAuthUtil
-    >("@web/auth/google/google.auth.util");
-    mockSyncPendingLocalEvents.mockImplementation(() => {
-      showLocalEventsSyncFailure(new Error("sync failed"));
-      return Promise.resolve(false);
-    });
-
-    renderHook(() => useConnectGoogle());
-
-    const useGoogleAuthArg = getUseGoogleAuthArg();
-    if (!useGoogleAuthArg?.onSuccess) {
-      throw new Error("Expected useGoogleAuth to receive an onSuccess handler");
-    }
-
-    const payload = {
-      clientType: "web" as const,
-      thirdPartyId: "google" as const,
-      redirectURIInfo: {
-        redirectURIOnProviderDashboard: window.location.origin,
-        redirectURIQueryParams: {
-          code: "auth-code",
-          scope: "scope",
-          state: "state",
-        },
-      },
-    };
-
-    await useGoogleAuthArg.onSuccess(payload);
-
-    expect(mockToastError).toHaveBeenCalled();
-    expect(mockAuthApi.connectGoogle).not.toHaveBeenCalled();
-    expect(mockRefreshUserMetadata).not.toHaveBeenCalled();
-    expect(mockDispatch).not.toHaveBeenCalledWith(triggerFetch());
-  });
-});
diff --git a/packages/web/src/auth/posthog/posthog.util.ts b/packages/web/src/auth/posthog/posthog.util.ts
new file mode 100644
index 000000000..9bb9c41ef
--- /dev/null
+++ b/packages/web/src/auth/posthog/posthog.util.ts
@@ -0,0 +1,5 @@
+import { ENV_WEB } from "@web/common/constants/env.constants";
+
+export function isPosthogEnabled() {
+  return !!ENV_WEB.POSTHOG_HOST && !!ENV_WEB.POSTHOG_KEY;
+}
diff --git a/packages/web/src/auth/posthog/useIdentifyUser.test.ts b/packages/web/src/auth/posthog/useIdentifyUser.test.ts
new file mode 100644
index 000000000..37314039f
--- /dev/null
+++ b/packages/web/src/auth/posthog/useIdentifyUser.test.ts
@@ -0,0 +1,89 @@
+import { type PostHog } from "posthog-js";
+import { usePostHog } from "posthog-js/react";
+import "@testing-library/jest-dom";
+import { renderHook, waitFor } from "@testing-library/react";
+import { useIdentifyUser } from "./useIdentifyUser";
+
+jest.mock("posthog-js/react");
+const mockUsePostHog = jest.mocked(usePostHog);
+
+const mockIdentify = jest.fn();
+
+function mockPostHogEnabled(overrides?: Partial<PostHog>): void {
+  mockUsePostHog.mockReturnValue({
+    identify: mockIdentify,
+    ...overrides,
+  } as unknown as PostHog);
+}
+
+function mockPostHogDisabled(): void {
+  mockUsePostHog.mockReturnValue(undefined as unknown as PostHog);
+}
+
+describe("useIdentifyUser", () => {
+  beforeEach(() => {
+    jest.clearAllMocks();
+    mockPostHogEnabled();
+  });
+
+  it("calls posthog.identify when PostHog is enabled and user data is available", async () => {
+    const testUserId = "test-user-123";
+    const testEmail = "test@example.com";
+
+    renderHook(() => useIdentifyUser(testEmail, testUserId));
+
+    await waitFor(() => {
+      expect(mockIdentify).toHaveBeenCalledWith(testEmail, {
+        email: testEmail,
+        userId: testUserId,
+      });
+    });
+    expect(mockIdentify).toHaveBeenCalledTimes(1);
+  });
+
+  it("does not call posthog.identify when PostHog is disabled", async () => {
+    mockPostHogDisabled();
+
+    renderHook(() => useIdentifyUser("test@example.com", "user-1"));
+
+    await waitFor(() => {
+      expect(mockUsePostHog).toHaveBeenCalled();
+    });
+
+    expect(mockIdentify).not.toHaveBeenCalled();
+  });
+
+  it("does not call posthog.identify when email is null", async () => {
+    renderHook(() => useIdentifyUser(null, "test-user-123"));
+
+    await waitFor(() => {
+      expect(mockUsePostHog).toHaveBeenCalled();
+    });
+
+    expect(mockIdentify).not.toHaveBeenCalled();
+  });
+
+  it("does not call posthog.identify when userId is null", async () => {
+    renderHook(() => useIdentifyUser("test@example.com", null));
+
+    await waitFor(() => {
+      expect(mockUsePostHog).toHaveBeenCalled();
+    });
+
+    expect(mockIdentify).not.toHaveBeenCalled();
+  });
+
+  it("handles posthog.identify not being a function gracefully", async () => {
+    mockPostHogEnabled({
+      identify: null as unknown as PostHog["identify"],
+    });
+
+    expect(() => {
+      renderHook(() => useIdentifyUser("test@example.com", "user-1"));
+    }).not.toThrow();
+
+    await waitFor(() => {
+      expect(mockIdentify).not.toHaveBeenCalled();
+    });
+  });
+});
diff --git a/packages/web/src/auth/posthog/useIdentifyUser.ts b/packages/web/src/auth/posthog/useIdentifyUser.ts
new file mode 100644
index 000000000..48b097069
--- /dev/null
+++ b/packages/web/src/auth/posthog/useIdentifyUser.ts
@@ -0,0 +1,22 @@
+import { usePostHog } from "posthog-js/react";
+import { useEffect } from "react";
+
+/**
+ * Identifies the user in PostHog when `userId` and profile email are available.
+ */
+export function useIdentifyUser(
+  profileEmail: string | null,
+  userId: string | null,
+): void {
+  const posthog = usePostHog();
+  useEffect(() => {
+    if (
+      userId &&
+      profileEmail &&
+      posthog &&
+      typeof posthog.identify === "function"
+    ) {
+      posthog.identify(profileEmail, { email: profileEmail, userId });
+    }
+  }, [profileEmail, posthog, userId]);
+}
diff --git a/packages/web/src/common/apis/auth.api.ts b/packages/web/src/common/apis/auth.api.ts
index f44948ceb..83bc27926 100644
--- a/packages/web/src/common/apis/auth.api.ts
+++ b/packages/web/src/common/apis/auth.api.ts
@@ -3,7 +3,7 @@ import {
   type GoogleConnectResponse,
   type Result_Auth_Compass,
 } from "@core/types/auth.types";
-import { type GoogleAuthConfig } from "@web/auth/hooks/google/googe.auth.types";
+import { type GoogleAuthConfig } from "@web/auth/google/hooks/googe.auth.types";
 import { CompassApi } from "@web/common/apis/compass.api";
 
 const AuthApi = {
diff --git a/packages/web/src/common/apis/compass.api.ts b/packages/web/src/common/apis/compass.api.ts
index 2e0a37921..7654a2fc8 100644
--- a/packages/web/src/common/apis/compass.api.ts
+++ b/packages/web/src/common/apis/compass.api.ts
@@ -6,7 +6,7 @@ import { session } from "@web/common/classes/Session";
 import { ENV_WEB } from "@web/common/constants/env.constants";
 import { ROOT_ROUTES } from "@web/common/constants/routes";
 import { showSessionExpiredToast } from "@web/common/utils/toast/error-toast.util";
-import { handleGoogleRevoked } from "../../auth/google/google.auth.util";
+import { handleGoogleRevoked } from "../../auth/google/util/google.auth.util";
 
 export const CompassApi = axios.create({
   baseURL: ENV_WEB.API_BASEURL,
diff --git a/packages/web/src/common/constants/auth.constants.ts b/packages/web/src/common/constants/auth.constants.ts
index d7888a89c..5c845962a 100644
--- a/packages/web/src/common/constants/auth.constants.ts
+++ b/packages/web/src/common/constants/auth.constants.ts
@@ -3,12 +3,14 @@ import { z } from "zod";
 export const AuthStateSchema = z.object({
   hasAuthenticated: z.boolean().default(false),
   lastKnownEmail: z.string().email().optional(),
+  shouldPromptSignUpAfterAnonymousCalendarChange: z.boolean().default(false),
 });
 
 export type AuthState = z.infer<typeof AuthStateSchema>;
 
 export const DEFAULT_AUTH_STATE: AuthState = {
   hasAuthenticated: false,
+  shouldPromptSignUpAfterAnonymousCalendarChange: false,
 };
 
 export const UNAUTHENTICATED_USER = "UNAUTHENTICATED_USER";
diff --git a/packages/web/src/common/hooks/useAuthCmdItems.test.ts b/packages/web/src/common/hooks/useAuthCmdItems.test.ts
index 5d755c8a9..d10f9b9ec 100644
--- a/packages/web/src/common/hooks/useAuthCmdItems.test.ts
+++ b/packages/web/src/common/hooks/useAuthCmdItems.test.ts
@@ -1,11 +1,11 @@
 import type { MouseEvent } from "react";
 import { act } from "react";
 import { renderHook } from "@testing-library/react";
-import { useSession } from "@web/auth/hooks/session/useSession";
+import { useSession } from "@web/auth/compass/session/useSession";
 import { useAuthModal } from "@web/components/AuthModal/hooks/useAuthModal";
 import { useAuthCmdItems } from "./useAuthCmdItems";
 
-jest.mock("@web/auth/hooks/session/useSession", () => ({
+jest.mock("@web/auth/compass/session/useSession", () => ({
   useSession: jest.fn(),
 }));
 
diff --git a/packages/web/src/common/hooks/useAuthCmdItems.ts b/packages/web/src/common/hooks/useAuthCmdItems.ts
index 28c982d6c..98a1b4c52 100644
--- a/packages/web/src/common/hooks/useAuthCmdItems.ts
+++ b/packages/web/src/common/hooks/useAuthCmdItems.ts
@@ -1,5 +1,5 @@
 import { type JsonStructureItem } from "react-cmdk";
-import { useSession } from "@web/auth/hooks/session/useSession";
+import { useSession } from "@web/auth/compass/session/useSession";
 import { useAuthFeatureFlag } from "@web/components/AuthModal/hooks/useAuthFeatureFlag";
 import { useAuthModal } from "@web/components/AuthModal/hooks/useAuthModal";
 
diff --git a/packages/web/src/common/hooks/useMainGridSelectionActions.ts b/packages/web/src/common/hooks/useMainGridSelectionActions.ts
index 1ceed47e5..01ce5bc55 100644
--- a/packages/web/src/common/hooks/useMainGridSelectionActions.ts
+++ b/packages/web/src/common/hooks/useMainGridSelectionActions.ts
@@ -1,6 +1,6 @@
 import { useCallback } from "react";
 import { Priorities } from "@core/constants/core.constants";
-import { getUserId } from "@web/auth/session/session.util";
+import { getUserId } from "@web/auth/compass/session/session.util";
 import {
   CursorItem,
   openFloatingAtCursor,
diff --git a/packages/web/src/common/repositories/event/event.repository.util.test.ts b/packages/web/src/common/repositories/event/event.repository.util.test.ts
index a1059d3a2..7b74c0794 100644
--- a/packages/web/src/common/repositories/event/event.repository.util.test.ts
+++ b/packages/web/src/common/repositories/event/event.repository.util.test.ts
@@ -1,12 +1,12 @@
-import * as googleAuthState from "@web/auth/google/google.auth.state";
-import * as authStateUtil from "@web/auth/state/auth.state.util";
+import * as authStateUtil from "@web/auth/compass/state/auth.state.util";
+import * as googleAuthState from "@web/auth/google/state/google.auth.state";
 import { getEventRepository } from "./event.repository.util";
 import { LocalEventRepository } from "./local.event.repository";
 import { RemoteEventRepository } from "./remote.event.repository";
 
 jest.mock("@web/common/classes/Session");
-jest.mock("@web/auth/google/google.auth.state");
-jest.mock("@web/auth/state/auth.state.util");
+jest.mock("@web/auth/google/state/google.auth.state");
+jest.mock("@web/auth/compass/state/auth.state.util");
 
 describe("getEventRepository", () => {
   beforeEach(() => {
diff --git a/packages/web/src/common/repositories/event/event.repository.util.ts b/packages/web/src/common/repositories/event/event.repository.util.ts
index f4b650db0..25ac9a5c2 100644
--- a/packages/web/src/common/repositories/event/event.repository.util.ts
+++ b/packages/web/src/common/repositories/event/event.repository.util.ts
@@ -1,5 +1,5 @@
-import { isGoogleRevoked } from "@web/auth/google/google.auth.state";
-import { hasUserEverAuthenticated } from "@web/auth/state/auth.state.util";
+import { hasUserEverAuthenticated } from "@web/auth/compass/state/auth.state.util";
+import { isGoogleRevoked } from "@web/auth/google/state/google.auth.state";
 import { type EventRepository } from "./event.repository.interface";
 import { LocalEventRepository } from "./local.event.repository";
 import { RemoteEventRepository } from "./remote.event.repository";
diff --git a/packages/web/src/common/types/icon.types.ts b/packages/web/src/common/types/icon.types.ts
deleted file mode 100644
index 1b47c8f8e..000000000
--- a/packages/web/src/common/types/icon.types.ts
+++ /dev/null
@@ -1,6 +0,0 @@
-export type ConnectionStatusIcon =
-  | "CloudArrowUpIcon"
-  | "LinkBreakIcon"
-  | "LinkIcon"
-  | "SpinnerIcon"
-  | "CloudWarningIcon";
diff --git a/packages/web/src/common/utils/draft/draft.util.test.ts b/packages/web/src/common/utils/draft/draft.util.test.ts
index 41c3fe23e..414e68b9f 100644
--- a/packages/web/src/common/utils/draft/draft.util.test.ts
+++ b/packages/web/src/common/utils/draft/draft.util.test.ts
@@ -1,7 +1,7 @@
 import { Categories_Event } from "@core/types/event.types";
 import { assembleDefaultEvent } from "../event/event.util";
 
-jest.mock("@web/auth/session/session.util", () => ({
+jest.mock("@web/auth/compass/session/session.util", () => ({
   getUserId: jest.fn().mockResolvedValue("mock-user-id"),
 }));
 describe("assembleDefaultEvent", () => {
diff --git a/packages/web/src/common/utils/event/event.util.ts b/packages/web/src/common/utils/event/event.util.ts
index 4c33e8d5b..eec52070f 100644
--- a/packages/web/src/common/utils/event/event.util.ts
+++ b/packages/web/src/common/utils/event/event.util.ts
@@ -8,7 +8,7 @@ import {
   type Schema_Event_Recur_Base,
 } from "@core/types/event.types";
 import dayjs, { type Dayjs } from "@core/util/date/dayjs";
-import { getUserId } from "@web/auth/session/session.util";
+import { getUserId } from "@web/auth/compass/session/session.util";
 import {
   CLASS_TIMED_CALENDAR_EVENT,
   DATA_EVENT_ELEMENT_ID,
diff --git a/packages/web/src/common/utils/overlap/overlap.test.ts b/packages/web/src/common/utils/overlap/overlap.test.ts
index 873f49304..a9e76dd6d 100644
--- a/packages/web/src/common/utils/overlap/overlap.test.ts
+++ b/packages/web/src/common/utils/overlap/overlap.test.ts
@@ -1,5 +1,5 @@
 import { Categories_Event } from "@core/types/event.types";
-import { getUserId } from "@web/auth/session/session.util";
+import { getUserId } from "@web/auth/compass/session/session.util";
 import { type Schema_GridEvent } from "@web/common/types/web.event.types";
 import {
   assembleDefaultEvent,
@@ -7,7 +7,7 @@ import {
 } from "../event/event.util";
 import { adjustOverlappingEvents, getOverlappingStyles } from "./overlap";
 
-jest.mock("@web/auth/session/session.util", () => ({
+jest.mock("@web/auth/compass/session/session.util", () => ({
   getUserId: jest.fn(),
 }));
 
diff --git a/packages/web/src/components/AuthModal/AccountIcon.tsx b/packages/web/src/components/AuthModal/AccountIcon.tsx
deleted file mode 100644
index f7ac7cccf..000000000
--- a/packages/web/src/components/AuthModal/AccountIcon.tsx
+++ /dev/null
@@ -1,45 +0,0 @@
-import { type FC } from "react";
-import { UserCircleDashedIcon, UserCircleIcon } from "@phosphor-icons/react";
-import { useSession } from "@web/auth/hooks/session/useSession";
-import { TooltipWrapper } from "@web/components/Tooltip/TooltipWrapper";
-import { useAuthFeatureFlag } from "./hooks/useAuthFeatureFlag";
-import { useAuthModal } from "./hooks/useAuthModal";
-
-/**
- * Account icon button for triggering the auth modal
- *
- */
-export const AccountIcon: FC = () => {
-  const { authenticated } = useSession();
-  const isEnabled = useAuthFeatureFlag();
-  const { openModal } = useAuthModal();
-
-  // Don't show if user is already authenticated or feature is disabled
-  if (authenticated || !isEnabled) {
-    return null;
-  }
-
-  const handleClick = () => {
-    openModal("login");
-  };
-
-  const tipDescription = authenticated ? "You're logged in" : "Log in";
-
-  return (
-    <TooltipWrapper description={tipDescription} onClick={handleClick}>
-      {authenticated ? (
-        <UserCircleIcon
-          size={24}
-          className="cursor-pointer text-white/70 transition-colors hover:text-white"
-          aria-label="Your account"
-        />
-      ) : (
-        <UserCircleDashedIcon
-          size={24}
-          className="cursor-pointer text-white/70 transition-colors hover:text-white"
-          aria-label="Log in"
-        />
-      )}
-    </TooltipWrapper>
-  );
-};
diff --git a/packages/web/src/components/AuthModal/AuthModal.test.tsx b/packages/web/src/components/AuthModal/AuthModal.test.tsx
index e7fdc254a..23223c781 100644
--- a/packages/web/src/components/AuthModal/AuthModal.test.tsx
+++ b/packages/web/src/components/AuthModal/AuthModal.test.tsx
@@ -22,20 +22,20 @@ const mockUseSession = jest.fn(() => ({
   setAuthenticated: jest.fn(),
 }));
 
-jest.mock("@web/auth/hooks/session/useSession", () => ({
+jest.mock("@web/auth/compass/session/useSession", () => ({
   useSession: () => mockUseSession(),
 }));
 
 // Mock useGoogleAuth
 const mockGoogleLogin = jest.fn();
-jest.mock("@web/auth/hooks/google/useGoogleAuth/useGoogleAuth", () => ({
+jest.mock("@web/auth/google/hooks/useGoogleAuth/useGoogleAuth", () => ({
   useGoogleAuth: () => ({
     login: mockGoogleLogin,
   }),
 }));
 
 const mockCompleteAuthentication = jest.fn();
-jest.mock("@web/auth/hooks/compass/useCompleteAuthentication", () => ({
+jest.mock("@web/auth/compass/hooks/useCompleteAuthentication", () => ({
   useCompleteAuthentication: () => mockCompleteAuthentication,
 }));
 
@@ -934,18 +934,6 @@ describe("URL Parameter Support", () => {
     ).not.toBeInTheDocument();
   });
 
-  it("implicitly enables auth feature when ?auth param is present", async () => {
-    mockWindowLocation("/?auth=signup");
-    renderWithProviders(<AccountIcon />, "/?auth=signup");
-
-    await waitFor(() => {
-      // The auth modal should open
-      expect(
-        screen.getByRole("heading", { name: /nice to meet you/i }),
-      ).toBeInTheDocument();
-    });
-  });
-
   it("works on different routes", async () => {
     mockWindowLocation("/week?auth=signup");
     renderWithProviders(<div />, "/week?auth=signup");
@@ -1047,66 +1035,3 @@ describe("URL Parameter Support", () => {
     });
   });
 });
-
-describe("AccountIcon", () => {
-  beforeEach(() => {
-    jest.clearAllMocks();
-  });
-
-  it("renders when user is not authenticated and feature flag is enabled", async () => {
-    mockUseSession.mockReturnValue({
-      authenticated: false,
-      setAuthenticated: jest.fn(),
-    });
-
-    renderWithProviders(<AccountIcon />, "/day?auth=signup");
-
-    await waitFor(() => {
-      expect(screen.getByLabelText(/log in/i)).toBeInTheDocument();
-    });
-  });
-
-  it("shows 'Log in' when user is not authenticated", () => {
-    mockUseSession.mockReturnValue({
-      authenticated: false,
-      setAuthenticated: jest.fn(),
-    });
-
-    renderWithProviders(<AccountIcon />, "/day?auth=signup");
-
-    expect(screen.getAllByText("Log in").length).toBeGreaterThan(0);
-  });
-
-  it("does not render when feature flag is disabled", () => {
-    mockUseSession.mockReturnValue({
-      authenticated: false,
-      setAuthenticated: jest.fn(),
-    });
-
-    renderWithProviders(<AccountIcon />, "/day");
-
-    expect(screen.queryByLabelText(/log in/i)).not.toBeInTheDocument();
-  });
-
-  it("opens modal when clicked", async () => {
-    const user = userEvent.setup();
-    mockUseSession.mockReturnValue({
-      authenticated: false,
-      setAuthenticated: jest.fn(),
-    });
-
-    renderWithProviders(<AccountIcon />, "/day?auth=signup");
-
-    await waitFor(() => {
-      expect(screen.getByLabelText(/log in/i)).toBeInTheDocument();
-    });
-
-    await user.click(screen.getByLabelText(/log in/i));
-
-    await waitFor(() => {
-      expect(
-        screen.getByRole("heading", { name: /hey, welcome back/i }),
-      ).toBeInTheDocument();
-    });
-  });
-});
diff --git a/packages/web/src/components/AuthModal/AuthModal.tsx b/packages/web/src/components/AuthModal/AuthModal.tsx
index d2e286d7e..9e00ffc86 100644
--- a/packages/web/src/components/AuthModal/AuthModal.tsx
+++ b/packages/web/src/components/AuthModal/AuthModal.tsx
@@ -1,6 +1,6 @@
 import { type FC, useCallback, useEffect, useRef, useState } from "react";
 import { DotIcon } from "@phosphor-icons/react";
-import { useGoogleAuth } from "@web/auth/hooks/google/useGoogleAuth/useGoogleAuth";
+import { useGoogleAuth } from "@web/auth/google/hooks/useGoogleAuth/useGoogleAuth";
 import { GoogleButton } from "@web/components/AuthModal/components/GoogleButton";
 import { OverlayPanel } from "@web/components/OverlayPanel/OverlayPanel";
 import { AuthButton } from "./components/AuthButton";
diff --git a/packages/web/src/components/AuthModal/forms/ForgotPasswordForm.tsx b/packages/web/src/components/AuthModal/forms/ForgotPasswordForm.tsx
index 36996028f..d0dbb2ec4 100644
--- a/packages/web/src/components/AuthModal/forms/ForgotPasswordForm.tsx
+++ b/packages/web/src/components/AuthModal/forms/ForgotPasswordForm.tsx
@@ -2,7 +2,7 @@ import { type ChangeEvent, type FC, useState } from "react";
 import {
   type ForgotPasswordFormData,
   ForgotPasswordSchema,
-} from "@web/auth/schemas/auth.schemas";
+} from "@web/auth/compass/schemas/auth.schemas";
 import { AuthButton } from "../components/AuthButton";
 import { AuthInput } from "../components/AuthInput";
 import { useZodForm } from "../hooks/useZodForm";
diff --git a/packages/web/src/components/AuthModal/forms/LogInForm.tsx b/packages/web/src/components/AuthModal/forms/LogInForm.tsx
index 9da4323bf..58e9fa415 100644
--- a/packages/web/src/components/AuthModal/forms/LogInForm.tsx
+++ b/packages/web/src/components/AuthModal/forms/LogInForm.tsx
@@ -2,7 +2,7 @@ import { type FC } from "react";
 import {
   type LogInFormData,
   LogInSchema,
-} from "@web/auth/schemas/auth.schemas";
+} from "@web/auth/compass/schemas/auth.schemas";
 import { AuthButton } from "../components/AuthButton";
 import { AuthInput } from "../components/AuthInput";
 import { useZodForm } from "../hooks/useZodForm";
diff --git a/packages/web/src/components/AuthModal/forms/ResetPasswordForm.tsx b/packages/web/src/components/AuthModal/forms/ResetPasswordForm.tsx
index 10d857f00..074535246 100644
--- a/packages/web/src/components/AuthModal/forms/ResetPasswordForm.tsx
+++ b/packages/web/src/components/AuthModal/forms/ResetPasswordForm.tsx
@@ -2,7 +2,7 @@ import { type FC } from "react";
 import {
   type ResetPasswordFormData,
   ResetPasswordSchema,
-} from "@web/auth/schemas/auth.schemas";
+} from "@web/auth/compass/schemas/auth.schemas";
 import { AuthButton } from "../components/AuthButton";
 import { AuthInput } from "../components/AuthInput";
 import { useZodForm } from "../hooks/useZodForm";
diff --git a/packages/web/src/components/AuthModal/forms/SignUpForm.tsx b/packages/web/src/components/AuthModal/forms/SignUpForm.tsx
index c0843ac4f..bf69ba336 100644
--- a/packages/web/src/components/AuthModal/forms/SignUpForm.tsx
+++ b/packages/web/src/components/AuthModal/forms/SignUpForm.tsx
@@ -2,7 +2,7 @@ import { type ChangeEvent, type FC, useCallback } from "react";
 import {
   type SignUpFormData,
   SignUpSchema,
-} from "@web/auth/schemas/auth.schemas";
+} from "@web/auth/compass/schemas/auth.schemas";
 import { AuthButton } from "../components/AuthButton";
 import { AuthInput } from "../components/AuthInput";
 import { useZodForm } from "../hooks/useZodForm";
diff --git a/packages/web/src/components/AuthModal/hooks/useAuthFeatureFlag.test.tsx b/packages/web/src/components/AuthModal/hooks/useAuthFeatureFlag.test.tsx
index e6f6391f6..57ec1e900 100644
--- a/packages/web/src/components/AuthModal/hooks/useAuthFeatureFlag.test.tsx
+++ b/packages/web/src/components/AuthModal/hooks/useAuthFeatureFlag.test.tsx
@@ -1,5 +1,5 @@
 import { renderHook } from "@testing-library/react";
-import { markUserAsAuthenticated } from "@web/auth/state/auth.state.util";
+import { markUserAsAuthenticated } from "@web/auth/compass/state/auth.state.util";
 import { useAuthFeatureFlag } from "./useAuthFeatureFlag";
 
 const setWindowLocation = (url: string) => {
diff --git a/packages/web/src/components/AuthModal/hooks/useAuthFeatureFlag.ts b/packages/web/src/components/AuthModal/hooks/useAuthFeatureFlag.ts
index ea704a278..db268ada2 100644
--- a/packages/web/src/components/AuthModal/hooks/useAuthFeatureFlag.ts
+++ b/packages/web/src/components/AuthModal/hooks/useAuthFeatureFlag.ts
@@ -1,4 +1,4 @@
-import { getLastKnownEmail } from "@web/auth/state/auth.state.util";
+import { getLastKnownEmail } from "@web/auth/compass/state/auth.state.util";
 
 /**
  * Feature flag hook for email/password authentication UI
diff --git a/packages/web/src/components/AuthModal/hooks/useAuthFormHandlers.ts b/packages/web/src/components/AuthModal/hooks/useAuthFormHandlers.ts
index ec039258c..5c0fbc6ba 100644
--- a/packages/web/src/components/AuthModal/hooks/useAuthFormHandlers.ts
+++ b/packages/web/src/components/AuthModal/hooks/useAuthFormHandlers.ts
@@ -1,13 +1,13 @@
 import { useCallback, useEffect, useMemo, useState } from "react";
 import EmailPassword from "supertokens-web-js/recipe/emailpassword";
 import { z } from "zod";
-import { useCompleteAuthentication } from "@web/auth/hooks/compass/useCompleteAuthentication";
+import { useCompleteAuthentication } from "@web/auth/compass/hooks/useCompleteAuthentication";
 import {
   type ForgotPasswordFormData,
   type LogInFormData,
   type ResetPasswordFormData,
   type SignUpFormData,
-} from "@web/auth/schemas/auth.schemas";
+} from "@web/auth/compass/schemas/auth.schemas";
 import { type AuthView } from "./useAuthModal";
 
 const AUTH_TOKEN_QUERY_SCHEMA = z.object({
diff --git a/packages/web/src/components/CompassProvider/CompassProvider.tsx b/packages/web/src/components/CompassProvider/CompassProvider.tsx
index a0c541405..ef2a9feae 100644
--- a/packages/web/src/components/CompassProvider/CompassProvider.tsx
+++ b/packages/web/src/components/CompassProvider/CompassProvider.tsx
@@ -5,7 +5,8 @@ import { ToastContainer } from "react-toastify";
 import { ThemeProvider } from "styled-components";
 import { GoogleOAuthProvider } from "@react-oauth/google";
 import { HotkeysProvider } from "@tanstack/react-hotkeys";
-import { SessionProvider } from "@web/auth/session/SessionProvider";
+import { SessionProvider } from "@web/auth/compass/session/SessionProvider";
+import { isPosthogEnabled } from "@web/auth/posthog/posthog.util";
 import { ENV_WEB } from "@web/common/constants/env.constants";
 import { CompassRefsProvider } from "@web/common/context/compass-refs";
 import { PointerPositionProvider } from "@web/common/context/pointer-position";
@@ -18,10 +19,6 @@ import { IconProvider } from "@web/components/IconProvider/IconProvider";
 import { store } from "@web/store";
 import { useGlobalShortcuts } from "@web/views/Calendar/hooks/shortcuts/useGlobalShortcuts";
 
-function isPosthogEnabled() {
-  return !!ENV_WEB.POSTHOG_HOST && !!ENV_WEB.POSTHOG_KEY;
-}
-
 /**
  * Mount once under {@link HotkeysProvider} and inside React Router so
  * {@link useGlobalShortcuts} can register app hotkeys (via useAppHotkey).
diff --git a/packages/web/src/components/HeaderInfoIcon/HeaderInfoIcon.test.tsx b/packages/web/src/components/HeaderInfoIcon/HeaderInfoIcon.test.tsx
new file mode 100644
index 000000000..bb885991d
--- /dev/null
+++ b/packages/web/src/components/HeaderInfoIcon/HeaderInfoIcon.test.tsx
@@ -0,0 +1,223 @@
+import type React from "react";
+import "@testing-library/jest-dom";
+import { render, screen } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
+import { type CompassSession } from "@web/auth/compass/session/session.types";
+import {
+  type GoogleUiConfig,
+  type GoogleUiState,
+} from "@web/auth/google/hooks/useConnectGoogle/useConnectGoogle.types";
+import { type AuthView } from "@web/components/AuthModal/hooks/useAuthModal";
+import { HeaderInfoIcon } from "./HeaderInfoIcon";
+
+interface MockConnectGoogleResult {
+  commandAction: GoogleUiConfig["commandAction"];
+  isRepairing: boolean;
+  sidebarStatus: GoogleUiConfig["sidebarStatus"];
+  state: GoogleUiState;
+}
+
+const mockOpenModal = jest.fn<void, [AuthView?]>();
+const mockGoogleOnSelect = jest.fn<void, []>();
+const mockUseSession = jest.fn<CompassSession, []>();
+const mockUseConnectGoogle = jest.fn<MockConnectGoogleResult, []>();
+const mockShouldShowAnonymousCalendarChangeSignUpPrompt = jest.fn<
+  boolean,
+  []
+>();
+const mockSubscribeToAuthState = jest.fn<() => void, [() => void]>(
+  () => () => {},
+);
+
+jest.mock("@web/auth/compass/session/useSession", () => ({
+  useSession: (): CompassSession => mockUseSession(),
+}));
+
+jest.mock("@web/auth/google/hooks/useConnectGoogle/useConnectGoogle", () => ({
+  useConnectGoogle: (): MockConnectGoogleResult => mockUseConnectGoogle(),
+}));
+
+jest.mock("@web/auth/compass/state/auth.state.util", () => ({
+  shouldShowAnonymousCalendarChangeSignUpPrompt: (): boolean =>
+    mockShouldShowAnonymousCalendarChangeSignUpPrompt(),
+  subscribeToAuthState: (listener: () => void): (() => void) =>
+    mockSubscribeToAuthState(listener),
+}));
+
+jest.mock("@web/components/AuthModal/hooks/useAuthModal", () => ({
+  useAuthModal: () => ({
+    openModal: mockOpenModal,
+  }),
+}));
+
+jest.mock("@phosphor-icons/react", () => ({
+  InfoIcon: ({ className }: { className?: string }) => (
+    <span aria-label="header-info-icon">{className ?? ""}</span>
+  ),
+  SpinnerGapIcon: () => <span aria-label="spinner-gap" />,
+}));
+
+jest.mock("@web/components/Tooltip/TooltipWrapper", () => ({
+  TooltipWrapper: ({
+    children,
+    description,
+    disabled,
+    onClick,
+  }: {
+    children: React.ReactNode;
+    description?: string;
+    disabled?: boolean;
+    onClick?: () => void;
+  }) => (
+    <button
+      aria-label={description}
+      disabled={disabled}
+      onClick={onClick}
+      type="button"
+    >
+      {children}
+    </button>
+  ),
+}));
+
+describe("HeaderInfoIcon", () => {
+  beforeEach(() => {
+    jest.clearAllMocks();
+    mockUseSession.mockReturnValue({
+      authenticated: false,
+      setAuthenticated: jest.fn(),
+    });
+    mockUseConnectGoogle.mockReturnValue({
+      commandAction: {
+        icon: "CloudArrowUpIcon",
+        isDisabled: false,
+        label: "Reconnect Google Calendar",
+        onSelect: mockGoogleOnSelect,
+      },
+      isRepairing: false,
+      sidebarStatus: {
+        iconColor: "error",
+        isDisabled: false,
+        onSelect: mockGoogleOnSelect,
+        tooltip: "Google Calendar needs reconnecting. Click to reconnect.",
+      },
+      state: "RECONNECT_REQUIRED",
+    });
+    mockShouldShowAnonymousCalendarChangeSignUpPrompt.mockReturnValue(false);
+  });
+
+  it("renders the anonymous sign-up warning dot and opens sign up when clicked", async () => {
+    const user = userEvent.setup();
+    mockShouldShowAnonymousCalendarChangeSignUpPrompt.mockReturnValue(true);
+
+    render(<HeaderInfoIcon />);
+
+    expect(
+      screen.getByRole("status", {
+        name: /sign up to save your changes/i,
+      }),
+    ).toBeInTheDocument();
+
+    await user.click(
+      screen.getByRole("button", {
+        name: /sign up to save your changes/i,
+      }),
+    );
+
+    expect(screen.getByLabelText("header-info-icon")).toHaveTextContent(
+      "motion-safe:animate-sync-dot-pulse",
+    );
+    expect(screen.getByLabelText("header-info-icon")).toHaveTextContent(
+      "motion-safe:group-hover:animate-none",
+    );
+    expect(mockOpenModal).toHaveBeenCalledWith("signUp");
+    expect(mockGoogleOnSelect).not.toHaveBeenCalled();
+  });
+
+  it("falls back to the existing Google status when the prompt is inactive", async () => {
+    const user = userEvent.setup();
+
+    render(<HeaderInfoIcon />);
+
+    expect(
+      screen.getByRole("status", {
+        name: /google calendar needs reconnecting/i,
+      }),
+    ).toBeInTheDocument();
+
+    await user.click(
+      screen.getByRole("button", {
+        name: /google calendar needs reconnecting/i,
+      }),
+    );
+
+    expect(screen.getByLabelText("header-info-icon")).not.toHaveTextContent(
+      "motion-safe:animate-sync-dot-pulse",
+    );
+    expect(mockGoogleOnSelect).toHaveBeenCalled();
+    expect(mockOpenModal).not.toHaveBeenCalled();
+  });
+
+  it("renders the background import spinner instead of the info icon while importing", () => {
+    mockUseConnectGoogle.mockReturnValue({
+      commandAction: {
+        icon: "CloudArrowUpIcon",
+        isDisabled: true,
+        label: "Syncing Google Calendar…",
+      },
+      isRepairing: false,
+      sidebarStatus: {
+        isDisabled: true,
+        tooltip: "Google Calendar is syncing in the background.",
+      },
+      state: "IMPORTING",
+    });
+
+    render(<HeaderInfoIcon />);
+
+    expect(
+      screen.getByRole("status", {
+        name: /syncing google calendar in the background/i,
+      }),
+    ).toBeInTheDocument();
+    expect(
+      screen.getByRole("button", {
+        name: /syncing google calendar in the background/i,
+      }),
+    ).toBeInTheDocument();
+    expect(screen.getByLabelText("spinner-gap")).toBeInTheDocument();
+    expect(screen.queryByLabelText("header-info-icon")).not.toBeInTheDocument();
+  });
+
+  it("renders the repairing spinner instead of the warning icon while repairing", () => {
+    mockUseConnectGoogle.mockReturnValue({
+      commandAction: {
+        icon: "CloudArrowUpIcon",
+        isDisabled: true,
+        label: "Repairing Google Calendar…",
+      },
+      isRepairing: true,
+      sidebarStatus: {
+        iconColor: "warning",
+        isDisabled: true,
+        tooltip: "Repairing Google Calendar in the background.",
+      },
+      state: "repairing",
+    });
+
+    render(<HeaderInfoIcon />);
+
+    expect(
+      screen.getByRole("status", {
+        name: /repairing google calendar in the background/i,
+      }),
+    ).toBeInTheDocument();
+    expect(
+      screen.getByRole("button", {
+        name: /repairing google calendar in the background/i,
+      }),
+    ).toBeInTheDocument();
+    expect(screen.getByLabelText("spinner-gap")).toBeInTheDocument();
+    expect(screen.queryByLabelText("header-info-icon")).not.toBeInTheDocument();
+  });
+});
diff --git a/packages/web/src/components/HeaderInfoIcon/HeaderInfoIcon.tsx b/packages/web/src/components/HeaderInfoIcon/HeaderInfoIcon.tsx
new file mode 100644
index 000000000..ad1fc0300
--- /dev/null
+++ b/packages/web/src/components/HeaderInfoIcon/HeaderInfoIcon.tsx
@@ -0,0 +1,86 @@
+import { InfoIcon } from "@phosphor-icons/react";
+import { type IconColor } from "@web/auth/google/hooks/useConnectGoogle/useConnectGoogle.types";
+import { theme } from "@web/common/styles/theme";
+import { SpinnerIcon } from "@web/components/Icons/Spinner";
+import { TooltipWrapper } from "@web/components/Tooltip/TooltipWrapper";
+import { StatusDotPopover } from "./HeaderInfoIconPopover";
+import { useHeaderInfo } from "./useHeaderInfo";
+
+const ICON_COLOR_MAP: Record<IconColor, string> = {
+  muted: theme.color.text.darkPlaceholder,
+  warning: theme.color.status.warning,
+  error: theme.color.status.error,
+};
+
+const ANONYMOUS_PROMPT_ICON_CLASSNAME =
+  "origin-center transition-all duration-200 ease-out motion-safe:animate-sync-dot-pulse motion-safe:group-hover:animate-none";
+const DOT_BUTTON_CLASSNAME = "inline-flex h-6 w-6 items-center justify-center";
+const ANONYMOUS_PROMPT_WRAPPER_CLASSNAME = `${DOT_BUTTON_CLASSNAME} group rounded-full transition-colors duration-200 ease-out hover:bg-white/20 hover:ring-1 hover:ring-white/20`;
+
+export const HeaderInfoIcon = () => {
+  const { isAnonymousSignUpPrompt, sidebarStatus, isRepairing, syncTooltip } =
+    useHeaderInfo();
+
+  if (syncTooltip) {
+    return (
+      <div role="status" aria-live="polite" aria-label={syncTooltip}>
+        <TooltipWrapper description={syncTooltip}>
+          <span className={DOT_BUTTON_CLASSNAME}>
+            <SpinnerIcon aria-hidden="true" />
+          </span>
+        </TooltipWrapper>
+      </div>
+    );
+  }
+
+  // Only render when user attention is needed (warning or error states)
+  if (
+    sidebarStatus.iconColor !== "warning" &&
+    sidebarStatus.iconColor !== "error"
+  ) {
+    return null;
+  }
+
+  const iconColor = ICON_COLOR_MAP[sidebarStatus.iconColor];
+  const iconClassName = isAnonymousSignUpPrompt
+    ? ANONYMOUS_PROMPT_ICON_CLASSNAME
+    : undefined;
+  const icon = (
+    <InfoIcon
+      aria-hidden="true"
+      className={iconClassName}
+      style={{ color: iconColor }}
+      size={15}
+    />
+  );
+  const wrappedIcon = isAnonymousSignUpPrompt ? (
+    <span className={ANONYMOUS_PROMPT_WRAPPER_CLASSNAME}>{icon}</span>
+  ) : (
+    <span className={DOT_BUTTON_CLASSNAME}>{icon}</span>
+  );
+
+  return (
+    <div role="status" aria-live="polite" aria-label={sidebarStatus.tooltip}>
+      {sidebarStatus.dialog ? (
+        <StatusDotPopover
+          tooltip={sidebarStatus.tooltip}
+          title={sidebarStatus.dialog.title}
+          description={sidebarStatus.dialog.description}
+          repairLabel={sidebarStatus.dialog.repairLabel}
+          onRepair={sidebarStatus.dialog.onRepair}
+          isRepairing={isRepairing}
+        >
+          {wrappedIcon}
+        </StatusDotPopover>
+      ) : (
+        <TooltipWrapper
+          description={sidebarStatus.tooltip}
+          disabled={sidebarStatus.isDisabled}
+          onClick={sidebarStatus.onSelect}
+        >
+          {wrappedIcon}
+        </TooltipWrapper>
+      )}
+    </div>
+  );
+};
diff --git a/packages/web/src/components/HeaderInfoIcon/HeaderInfoIconPopover.tsx b/packages/web/src/components/HeaderInfoIcon/HeaderInfoIconPopover.tsx
new file mode 100644
index 000000000..ba41613fe
--- /dev/null
+++ b/packages/web/src/components/HeaderInfoIcon/HeaderInfoIconPopover.tsx
@@ -0,0 +1,109 @@
+import { useState } from "react";
+import {
+  FloatingFocusManager,
+  FloatingPortal,
+  autoUpdate,
+  flip,
+  offset,
+  shift,
+  useClick,
+  useDismiss,
+  useFloating,
+  useInteractions,
+  useRole,
+} from "@floating-ui/react";
+import { SpinnerIcon } from "@phosphor-icons/react";
+import { ZIndex } from "@web/common/constants/web.constants";
+import { useGridMaxZIndex } from "@web/common/hooks/useGridMaxZIndex";
+import { TooltipWrapper } from "../Tooltip/TooltipWrapper";
+
+interface StatusDotPopoverProps {
+  children: React.ReactNode;
+  tooltip: string;
+  title: string;
+  description: string;
+  repairLabel: string;
+  onRepair: () => void;
+  isRepairing: boolean;
+}
+export const StatusDotPopover = ({
+  children,
+  tooltip,
+  title,
+  description,
+  repairLabel,
+  onRepair,
+  isRepairing,
+}: StatusDotPopoverProps) => {
+  const [open, setOpen] = useState(false);
+  const maxZIndex = useGridMaxZIndex();
+
+  const { refs, floatingStyles, context } = useFloating({
+    open,
+    onOpenChange: setOpen,
+    placement: "bottom",
+    whileElementsMounted: autoUpdate,
+    middleware: [offset(8), flip(), shift({ padding: 8 })],
+  });
+
+  const click = useClick(context);
+  const dismiss = useDismiss(context);
+  const role = useRole(context, { role: "dialog" });
+
+  const { getReferenceProps, getFloatingProps } = useInteractions([
+    click,
+    dismiss,
+    role,
+  ]);
+
+  const displayTitle = isRepairing ? "Repairing your calendar…" : title;
+
+  return (
+    <>
+      <div ref={refs.setReference} {...getReferenceProps()}>
+        <TooltipWrapper description={tooltip}>{children}</TooltipWrapper>
+      </div>
+
+      {open && (
+        <FloatingPortal>
+          <FloatingFocusManager context={context} modal={false}>
+            <div
+              ref={refs.setFloating}
+              style={{
+                ...floatingStyles,
+                zIndex: maxZIndex + ZIndex.LAYER_3,
+              }}
+              className="border-border-primary bg-bg-secondary/90 flex max-w-xs flex-col gap-3 rounded-lg border p-4 shadow-lg"
+              aria-label={displayTitle}
+              {...getFloatingProps()}
+            >
+              <h3 className="text-text-lighter m-0 text-sm font-semibold">
+                {displayTitle}
+              </h3>
+              {!isRepairing && (
+                <p className="text-text-lighter m-0 text-sm">{description}</p>
+              )}
+              {isRepairing ? (
+                <button
+                  disabled
+                  className="flex cursor-not-allowed items-center justify-center self-start rounded px-3 py-1.5 opacity-50"
+                  type="button"
+                >
+                  <SpinnerIcon aria-hidden="true" size={16} />
+                </button>
+              ) : (
+                <button
+                  className="bg-bg-accent text-text-light hover:bg-bg-accent/80 self-start rounded px-3 py-1.5 text-sm font-medium"
+                  onClick={onRepair}
+                  type="button"
+                >
+                  {repairLabel}
+                </button>
+              )}
+            </div>
+          </FloatingFocusManager>
+        </FloatingPortal>
+      )}
+    </>
+  );
+};
diff --git a/packages/web/src/components/HeaderInfoIcon/useHeaderInfo.ts b/packages/web/src/components/HeaderInfoIcon/useHeaderInfo.ts
new file mode 100644
index 000000000..d67269f97
--- /dev/null
+++ b/packages/web/src/components/HeaderInfoIcon/useHeaderInfo.ts
@@ -0,0 +1,63 @@
+import { useCallback, useSyncExternalStore } from "react";
+import { useSession } from "@web/auth/compass/session/useSession";
+import {
+  shouldShowAnonymousCalendarChangeSignUpPrompt,
+  subscribeToAuthState,
+} from "@web/auth/compass/state/auth.state.util";
+import { useConnectGoogle } from "@web/auth/google/hooks/useConnectGoogle/useConnectGoogle";
+import {
+  type GoogleUiConfig,
+  type UseConnectGoogleResult,
+} from "@web/auth/google/hooks/useConnectGoogle/useConnectGoogle.types";
+import { useAuthModal } from "@web/components/AuthModal/hooks/useAuthModal";
+
+const ANONYMOUS_SIGN_UP_TOOLTIP = "Sign up to save your changes.";
+
+interface HeaderInfo {
+  isAnonymousSignUpPrompt: boolean;
+  isRepairing: UseConnectGoogleResult["isRepairing"];
+  sidebarStatus: GoogleUiConfig["sidebarStatus"];
+  syncTooltip: null | string;
+}
+
+export const useHeaderInfo = (): HeaderInfo => {
+  const { authenticated } = useSession();
+  const { openModal } = useAuthModal();
+  const googleStatus = useConnectGoogle();
+  const shouldPromptSignUp = useSyncExternalStore(
+    subscribeToAuthState,
+    shouldShowAnonymousCalendarChangeSignUpPrompt,
+    shouldShowAnonymousCalendarChangeSignUpPrompt,
+  );
+
+  const handleOpenSignUp = useCallback(() => {
+    openModal("signUp");
+  }, [openModal]);
+
+  if (!authenticated && shouldPromptSignUp) {
+    return {
+      isAnonymousSignUpPrompt: true,
+      isRepairing: false,
+      sidebarStatus: {
+        iconColor: "warning" as const,
+        isDisabled: false,
+        onSelect: handleOpenSignUp,
+        tooltip: ANONYMOUS_SIGN_UP_TOOLTIP,
+      },
+      syncTooltip: null,
+    };
+  }
+
+  const syncTooltip =
+    googleStatus.state === "repairing"
+      ? "Repairing Google Calendar in the background."
+      : googleStatus.state === "IMPORTING"
+        ? "Syncing Google Calendar in the background."
+        : null;
+
+  return {
+    isAnonymousSignUpPrompt: false,
+    ...googleStatus,
+    syncTooltip,
+  };
+};
diff --git a/packages/web/src/components/Icons/CircleIcon.tsx b/packages/web/src/components/Icons/CircleIcon.tsx
index 8399e0839..89c3a57c4 100644
--- a/packages/web/src/components/Icons/CircleIcon.tsx
+++ b/packages/web/src/components/Icons/CircleIcon.tsx
@@ -1,4 +1,6 @@
-export const CircleIcon = () => {
+import { type ComponentProps } from "react";
+
+export const CircleIcon = (props: ComponentProps<"svg">) => {
   return (
     <svg
       width="12"
@@ -7,6 +9,7 @@ export const CircleIcon = () => {
       fill="none"
       xmlns="http://www.w3.org/2000/svg"
       aria-hidden="true"
+      {...props}
     >
       <circle cx="6" cy="6" r="3" fill="currentColor" />
     </svg>
diff --git a/packages/web/src/components/Icons/Info.tsx b/packages/web/src/components/Icons/Info.tsx
deleted file mode 100644
index 0ead2b030..000000000
--- a/packages/web/src/components/Icons/Info.tsx
+++ /dev/null
@@ -1,7 +0,0 @@
-import styled from "styled-components";
-import { Info } from "@phosphor-icons/react";
-import { iconStyles } from "./styled";
-
-export const InfoIcon = styled(Info)`
-  ${iconStyles}
-`;
diff --git a/packages/web/src/components/Icons/Spinner.tsx b/packages/web/src/components/Icons/Spinner.tsx
index 9b23c8714..a60c04eed 100644
--- a/packages/web/src/components/Icons/Spinner.tsx
+++ b/packages/web/src/components/Icons/Spinner.tsx
@@ -1,9 +1,9 @@
 import styled from "styled-components";
-import { SpinnerGap } from "@phosphor-icons/react";
+import { SpinnerGapIcon } from "@phosphor-icons/react";
 import { rotateAnimation } from "@web/common/styles/animations/rotate";
 import { iconStyles } from "./styled";
 
-export const SpinnerIcon = styled(SpinnerGap)`
+export const SpinnerIcon = styled(SpinnerGapIcon)`
   ${iconStyles}
   animation: ${rotateAnimation};
 `;
diff --git a/packages/web/src/ducks/events/sagas/event.sagas.prompt.test.ts b/packages/web/src/ducks/events/sagas/event.sagas.prompt.test.ts
new file mode 100644
index 000000000..dc1c978c6
--- /dev/null
+++ b/packages/web/src/ducks/events/sagas/event.sagas.prompt.test.ts
@@ -0,0 +1,134 @@
+import { runSaga } from "redux-saga";
+import { type Schema_Event } from "@core/types/event.types";
+import { createMockStandaloneEvent } from "@core/util/test/ccal.event.factory";
+import { session } from "@web/common/classes/Session";
+import { getEventRepository } from "@web/common/repositories/event/event.repository.util";
+import type * as SagaUtil from "@web/ducks/events/sagas/saga.util";
+import { createEvent, editEvent } from "./event.sagas";
+
+const mockHandleError = jest.fn<void, [unknown]>();
+const mockMarkAnonymousCalendarChangeForSignUpPrompt = jest.fn<void, []>();
+const mockCreateOptimisticGridEvent = jest.fn<
+  Generator<unknown, Schema_Event, unknown>,
+  unknown[]
+>();
+
+jest.mock("@web/common/classes/Session", () => ({
+  session: {
+    doesSessionExist: jest.fn(),
+  },
+}));
+
+jest.mock("@web/common/repositories/event/event.repository.util", () => ({
+  getEventRepository: jest.fn(),
+}));
+
+jest.mock("@web/auth/google/state/google.auth.state", () => ({
+  isGoogleRevoked: jest.fn<boolean, []>(() => false),
+}));
+
+jest.mock("@web/auth/compass/state/auth.state.util", () => ({
+  hasUserEverAuthenticated: jest.fn<boolean, []>(() => false),
+  markAnonymousCalendarChangeForSignUpPrompt: (): void => {
+    mockMarkAnonymousCalendarChangeForSignUpPrompt();
+  },
+}));
+
+jest.mock("@web/common/utils/event/event.util", () => ({
+  handleError: (...args: [unknown]) => mockHandleError(...args),
+}));
+
+jest.mock("@web/ducks/events/sagas/saga.util", () => {
+  const actual: typeof SagaUtil = jest.requireActual(
+    "@web/ducks/events/sagas/saga.util",
+  );
+
+  return {
+    ...actual,
+    _createOptimisticGridEvent: (...args: unknown[]) =>
+      mockCreateOptimisticGridEvent(...args),
+  };
+});
+
+describe("event sign-up prompt failure paths", () => {
+  const mockEvent = {
+    ...createMockStandaloneEvent(),
+    _id: "event-1",
+    isSomeday: false,
+  } as Schema_Event;
+
+  beforeEach(() => {
+    jest.clearAllMocks();
+    (session.doesSessionExist as jest.Mock).mockResolvedValue(false);
+    // eslint-disable-next-line require-yield
+    mockCreateOptimisticGridEvent.mockImplementation(function* () {
+      return mockEvent;
+    });
+  });
+
+  it("does not mark the sign-up prompt when anonymous create fails", async () => {
+    const repository = {
+      create: jest.fn().mockRejectedValue(new Error("create failed")),
+      delete: jest.fn().mockResolvedValue(undefined),
+      edit: jest.fn(),
+    };
+    (getEventRepository as jest.Mock).mockReturnValue(repository);
+
+    await runSaga(
+      {
+        dispatch: jest.fn(),
+        getState: () => ({
+          events: {
+            entities: { value: {} },
+            pendingEvents: { eventIds: [] },
+          },
+        }),
+      },
+      createEvent,
+      { payload: mockEvent } as never,
+    ).toPromise();
+
+    expect(
+      mockMarkAnonymousCalendarChangeForSignUpPrompt,
+    ).not.toHaveBeenCalled();
+  });
+
+  it("does not mark the sign-up prompt when anonymous edit fails", async () => {
+    const repository = {
+      create: jest.fn(),
+      delete: jest.fn(),
+      edit: jest.fn().mockRejectedValue(new Error("edit failed")),
+    };
+    (getEventRepository as jest.Mock).mockReturnValue(repository);
+
+    await runSaga(
+      {
+        dispatch: jest.fn(),
+        getState: () => ({
+          events: {
+            entities: {
+              value: {
+                [mockEvent._id]: mockEvent,
+              },
+            },
+            pendingEvents: { eventIds: [] },
+          },
+        }),
+      },
+      editEvent,
+      {
+        payload: {
+          _id: mockEvent._id,
+          event: {
+            ...mockEvent,
+            title: "Updated Title",
+          },
+        },
+      } as never,
+    ).toPromise();
+
+    expect(
+      mockMarkAnonymousCalendarChangeForSignUpPrompt,
+    ).not.toHaveBeenCalled();
+  });
+});
diff --git a/packages/web/src/ducks/events/sagas/event.sagas.test.ts b/packages/web/src/ducks/events/sagas/event.sagas.test.ts
index c42c5a0fa..4a13659b6 100644
--- a/packages/web/src/ducks/events/sagas/event.sagas.test.ts
+++ b/packages/web/src/ducks/events/sagas/event.sagas.test.ts
@@ -2,6 +2,12 @@ import { type AxiosResponse } from "axios";
 import { type Schema_Event } from "@core/types/event.types";
 import { createMockStandaloneEvent } from "@core/util/test/ccal.event.factory";
 import { createStoreWithEvents } from "@web/__tests__/utils/state/store.test.util";
+import {
+  clearAnonymousCalendarChangeSignUpPrompt,
+  clearAuthenticationState,
+  shouldShowAnonymousCalendarChangeSignUpPrompt,
+  updateAuthState,
+} from "@web/auth/compass/state/auth.state.util";
 import { session } from "@web/common/classes/Session";
 import {
   ensureStorageReady,
@@ -35,6 +41,7 @@ beforeEach(() => {
 
 afterEach(() => {
   jest.restoreAllMocks();
+  clearAuthenticationState();
 });
 
 describe("createEvent saga - optimistic rendering", () => {
@@ -469,6 +476,7 @@ describe("createEvent saga - unauthenticated users", () => {
 
   beforeEach(async () => {
     jest.clearAllMocks();
+    clearAuthenticationState();
     try {
       await ensureStorageReady();
       await getStorageAdapter().clearAllEvents();
@@ -560,4 +568,61 @@ describe("createEvent saga - unauthenticated users", () => {
     const isPending = selectIsEventPending(state, eventId);
     expect(isPending).toBe(false);
   });
+
+  it("should mark the sign-up prompt after anonymous event creation", async () => {
+    const gridEvent = createMockStandaloneEvent() as Schema_GridEvent;
+    const event = new OnSubmitParser(gridEvent).parse() as Schema_Event;
+
+    store.dispatch(createEventSlice.actions.request(event));
+
+    await new Promise((resolve) => setTimeout(resolve, 100));
+
+    expect(shouldShowAnonymousCalendarChangeSignUpPrompt()).toBe(true);
+  });
+
+  it("should mark the sign-up prompt after anonymous event edit", async () => {
+    const gridEvent = createMockStandaloneEvent() as Schema_GridEvent;
+    const event = new OnSubmitParser(gridEvent).parse() as Schema_Event;
+
+    store.dispatch(createEventSlice.actions.request(event));
+    await new Promise((resolve) => setTimeout(resolve, 100));
+
+    clearAnonymousCalendarChangeSignUpPrompt();
+
+    const stateAfterCreate = store.getState();
+    const eventId = Object.keys(
+      stateAfterCreate.events.entities.value || {},
+    )[0];
+    const existingEvent = selectEventById(
+      stateAfterCreate,
+      eventId,
+    ) as Schema_GridEvent;
+
+    store.dispatch(
+      editEventSlice.actions.request({
+        _id: eventId,
+        event: {
+          ...existingEvent,
+          title: "Updated Title",
+        } as Schema_WebEvent,
+      }),
+    );
+
+    await new Promise((resolve) => setTimeout(resolve, 100));
+
+    expect(shouldShowAnonymousCalendarChangeSignUpPrompt()).toBe(true);
+  });
+
+  it("should not mark the sign-up prompt for previously authenticated users", async () => {
+    updateAuthState({ hasAuthenticated: true });
+
+    const gridEvent = createMockStandaloneEvent() as Schema_GridEvent;
+    const event = new OnSubmitParser(gridEvent).parse() as Schema_Event;
+
+    store.dispatch(createEventSlice.actions.request(event));
+
+    await new Promise((resolve) => setTimeout(resolve, 100));
+
+    expect(shouldShowAnonymousCalendarChangeSignUpPrompt()).toBe(false);
+  });
 });
diff --git a/packages/web/src/ducks/events/sagas/event.sagas.ts b/packages/web/src/ducks/events/sagas/event.sagas.ts
index 790d72f34..69199db96 100644
--- a/packages/web/src/ducks/events/sagas/event.sagas.ts
+++ b/packages/web/src/ducks/events/sagas/event.sagas.ts
@@ -7,6 +7,11 @@ import {
   type Schema_Event,
 } from "@core/types/event.types";
 import dayjs from "@core/util/date/dayjs";
+import {
+  hasUserEverAuthenticated,
+  markAnonymousCalendarChangeForSignUpPrompt,
+} from "@web/auth/compass/state/auth.state.util";
+import { isGoogleRevoked } from "@web/auth/google/state/google.auth.state";
 import { session } from "@web/common/classes/Session";
 import { getEventRepository } from "@web/common/repositories/event/event.repository.util";
 import { type Response_HttpPaginatedSuccess } from "@web/common/types/api.types";
@@ -47,6 +52,10 @@ import { pendingEventsSlice } from "@web/ducks/events/slices/pending.slice";
 import { getWeekEventsSlice } from "@web/ducks/events/slices/week.slice";
 import { type RootState } from "@web/store";
 
+function shouldPromptAnonymousSignUp(sessionExists: boolean): boolean {
+  return !sessionExists && !hasUserEverAuthenticated() && !isGoogleRevoked();
+}
+
 export function* convertCalendarToSomedayEvent({
   payload,
 }: Action_ConvertEvent) {
@@ -99,10 +108,16 @@ export function* createEvent({ payload }: Action_CreateEvent): Generator {
   yield put(pendingEventsSlice.actions.add(event._id));
 
   try {
-    const sessionExists = yield call(session.doesSessionExist);
+    const sessionExists = (yield call([
+      session,
+      "doesSessionExist",
+    ])) as boolean;
     const repository = getEventRepository(sessionExists);
 
-    yield call([repository, repository.create], event as Schema_Event);
+    yield call([repository, "create"], event as Schema_Event);
+    if (shouldPromptAnonymousSignUp(sessionExists)) {
+      markAnonymousCalendarChangeForSignUpPrompt();
+    }
 
     yield put(
       eventsEntitiesSlice.actions.edit({
@@ -135,9 +150,12 @@ export function* deleteEvent({ payload }: Action_DeleteEvent) {
     const isPending = pendingEventIds.includes(payload._id);
     // Only call delete if event is not pending (i.e., exists in DB)
     if (!isPending) {
-      const sessionExists = yield call(session.doesSessionExist);
+      const sessionExists = (yield call([
+        session,
+        "doesSessionExist",
+      ])) as boolean;
       const repository = getEventRepository(sessionExists);
-      yield call([repository, repository.delete], payload._id, payload.applyTo);
+      yield call([repository, "delete"], payload._id, payload.applyTo);
     }
 
     yield put(deleteEventSlice.actions.success());
@@ -161,11 +179,17 @@ export function* editEvent({ payload }: Action_EditEvent) {
     if (shouldRemove) yield put(eventsEntitiesSlice.actions.delete({ _id }));
     else yield put(eventsEntitiesSlice.actions.edit(payload));
 
-    const sessionExists = yield call(session.doesSessionExist);
+    const sessionExists = (yield call([
+      session,
+      "doesSessionExist",
+    ])) as boolean;
     const repository = getEventRepository(sessionExists);
-    yield call([repository, repository.edit], _id, event as Schema_Event, {
+    yield call([repository, "edit"], _id, event as Schema_Event, {
       applyTo,
     });
+    if (shouldPromptAnonymousSignUp(sessionExists)) {
+      markAnonymousCalendarChangeForSignUpPrompt();
+    }
 
     // Remove from pending on success
     yield put(pendingEventsSlice.actions.remove(_id));
@@ -205,15 +229,18 @@ function* getEvents(
       return { data: payload.data };
     }
 
-    const sessionExists = yield call(session.doesSessionExist);
+    const sessionExists = (yield call([
+      session,
+      "doesSessionExist",
+    ])) as boolean;
     const repository = getEventRepository(sessionExists);
 
     const _payload = EventDateUtils.adjustStartEndDate(payload);
 
-    const res: Response_GetEventsSuccess = yield call(
-      [repository, repository.get],
+    const res = (yield call(
+      [repository, "get"],
       _payload,
-    );
+    )) as Response_GetEventsSuccess;
 
     const events = EventDateUtils.filterEventsByStartEndDate(
       res.data,
diff --git a/packages/web/src/ducks/events/sagas/sync.sagas.ts b/packages/web/src/ducks/events/sagas/sync.sagas.ts
deleted file mode 100644
index e6384b475..000000000
--- a/packages/web/src/ducks/events/sagas/sync.sagas.ts
+++ /dev/null
@@ -1,26 +0,0 @@
-import { call, put } from "@redux-saga/core/effects";
-import { handleError } from "@web/common/utils/event/event.util";
-import { SyncApi } from "../../../common/apis/sync.api";
-import { importGCalSlice } from "../slices/sync.slice";
-
-type NoArgActionCreator<T> = T extends (...args: never[]) => infer R
-  ? () => R
-  : never;
-
-const successAction = importGCalSlice.actions
-  .success as unknown as NoArgActionCreator<
-  typeof importGCalSlice.actions.success
->;
-
-const errorAction = importGCalSlice.actions
-  .error as unknown as NoArgActionCreator<typeof importGCalSlice.actions.error>;
-
-export function* importGCal() {
-  try {
-    yield call(SyncApi.importGCal);
-    yield put(successAction());
-  } catch (error) {
-    yield put(errorAction());
-    handleError(error as Error);
-  }
-}
diff --git a/packages/web/src/ducks/events/selectors/sync.selector.ts b/packages/web/src/ducks/events/selectors/sync.selector.ts
index dca25bdc1..f4d9a4cb6 100644
--- a/packages/web/src/ducks/events/selectors/sync.selector.ts
+++ b/packages/web/src/ducks/events/selectors/sync.selector.ts
@@ -2,11 +2,3 @@ import { type RootState } from "@web/store";
 
 export const selectImportLatestState = ({ sync }: RootState) =>
   sync.importLatest;
-
-export const selectImportGCalState = ({ sync }: RootState) => sync.importGCal;
-
-export const selectImportResults = ({ sync }: RootState) =>
-  sync.importGCal.importResults;
-
-export const selectImportError = ({ sync }: RootState) =>
-  sync.importGCal.importError;
diff --git a/packages/web/src/ducks/events/slices/sync.slice.ts b/packages/web/src/ducks/events/slices/sync.slice.ts
index 796810428..8dce0976c 100644
--- a/packages/web/src/ducks/events/slices/sync.slice.ts
+++ b/packages/web/src/ducks/events/slices/sync.slice.ts
@@ -1,5 +1,4 @@
 import { type PayloadAction, createSlice } from "@reduxjs/toolkit";
-import { type AsyncState, createAsyncSlice } from "@web/common/store/helpers";
 import { type Sync_AsyncStateContextReason } from "@web/ducks/events/context/sync.context";
 
 type Payload_TriggerFetch = {
@@ -22,77 +21,6 @@ export interface ImportResults {
   localEventsSynced?: number;
 }
 
-type ImportGCalExtraState = {
-  isRepairing: boolean;
-  importResults: ImportResults | null;
-  pendingLocalEventsSynced: number | null;
-  importError: string | null;
-};
-
-const importGCalReducers = {
-  startRepair: (
-    state: AsyncState<undefined, undefined> & ImportGCalExtraState,
-  ) => {
-    state.isRepairing = true;
-  },
-  stopRepair: (
-    state: AsyncState<undefined, undefined> & ImportGCalExtraState,
-  ) => {
-    state.isRepairing = false;
-  },
-  setLocalEventsSynced: (
-    state: AsyncState<undefined, undefined> & ImportGCalExtraState,
-    action: PayloadAction<number>,
-  ) => {
-    state.pendingLocalEventsSynced = action.payload;
-  },
-  setImportResults: (
-    state: AsyncState<undefined, undefined> & ImportGCalExtraState,
-    action: PayloadAction<{
-      eventsCount?: number;
-      calendarsCount?: number;
-    }>,
-  ) => {
-    state.importError = null;
-    state.importResults = {
-      ...action.payload,
-      localEventsSynced: state.pendingLocalEventsSynced ?? undefined,
-    };
-    state.pendingLocalEventsSynced = null;
-  },
-  setImportError: (
-    state: AsyncState<undefined, undefined> & ImportGCalExtraState,
-    action: PayloadAction<string>,
-  ) => {
-    state.importError = action.payload;
-    state.importResults = null;
-    state.pendingLocalEventsSynced = null;
-  },
-  clearImportResults: (
-    state: AsyncState<undefined, undefined> & ImportGCalExtraState,
-  ) => {
-    state.importResults = null;
-    state.importError = null;
-  },
-};
-
-export const importGCalSlice = createAsyncSlice<
-  never,
-  undefined,
-  undefined,
-  ImportGCalExtraState,
-  typeof importGCalReducers
->({
-  name: "importGCal",
-  initialState: {
-    isRepairing: false,
-    importResults: null,
-    pendingLocalEventsSynced: null,
-    importError: null,
-  },
-  reducers: importGCalReducers,
-});
-
 export const importLatestSlice = createSlice({
   name: "importLatest",
   initialState,
diff --git a/packages/web/src/index.css b/packages/web/src/index.css
index 42531d00a..ab731e08f 100644
--- a/packages/web/src/index.css
+++ b/packages/web/src/index.css
@@ -78,6 +78,7 @@
 
   /* Animations */
   --animate-progress-slide: progressSlide 2s ease-out infinite;
+  --animate-sync-dot-pulse: syncDotPulse 2.4s ease-in-out infinite;
 
   @keyframes progressSlide {
     0% {
@@ -87,6 +88,19 @@
       width: 600%;
     }
   }
+
+  @keyframes syncDotPulse {
+    0%,
+    100% {
+      opacity: 0.88;
+      transform: scale(0.96);
+    }
+
+    50% {
+      opacity: 1;
+      transform: scale(1);
+    }
+  }
 }
 
 @layer base {
diff --git a/packages/web/src/index.tsx b/packages/web/src/index.tsx
index 9ddb368ea..0ef6527b5 100644
--- a/packages/web/src/index.tsx
+++ b/packages/web/src/index.tsx
@@ -1,7 +1,7 @@
 import "react-datepicker/dist/react-datepicker.css";
 import { createRoot } from "react-dom/client";
 import "react-toastify/dist/ReactToastify.css";
-import { sessionInit } from "@web/auth/session/SessionProvider";
+import { sessionInit } from "@web/auth/compass/session/SessionProvider";
 import { sagaMiddleware } from "@web/common/store/middlewares";
 import {
   initializeDatabaseWithErrorHandling,
diff --git a/packages/web/src/sse/hooks/useGcalSSE.ts b/packages/web/src/sse/hooks/useGcalSSE.ts
index 5cab2c8c3..da370dd0c 100644
--- a/packages/web/src/sse/hooks/useGcalSSE.ts
+++ b/packages/web/src/sse/hooks/useGcalSSE.ts
@@ -1,36 +1,36 @@
 import { useCallback, useEffect } from "react";
-import { useDispatch } from "react-redux";
 import {
   GOOGLE_REVOKED,
   IMPORT_GCAL_END,
+  IMPORT_GCAL_START,
   USER_METADATA,
 } from "@core/constants/sse.constants";
 import { type ImportGCalEndPayload } from "@core/types/sse.types";
 import { type UserMetadata } from "@core/types/user.types";
-import { handleGoogleRevoked } from "@web/auth/google/google.auth.util";
-import { refreshUserMetadata } from "@web/auth/session/user-metadata.util";
+import { refreshUserMetadata } from "@web/auth/compass/user/util/user-metadata.util";
+import {
+  clearGoogleSyncIndicatorOverride,
+  getGoogleSyncIndicatorOverride,
+  setSyncingSyncIndicatorOverride,
+} from "@web/auth/google/state/google.sync.state";
+import { handleGoogleRevoked } from "@web/auth/google/util/google.auth.util";
 import { GOOGLE_REPAIR_FAILED_TOAST_ID } from "@web/common/constants/toast.constants";
 import { showErrorToast } from "@web/common/utils/toast/error-toast.util";
 import { userMetadataSlice } from "@web/ducks/auth/slices/user-metadata.slice";
 import { Sync_AsyncStateContextReason } from "@web/ducks/events/context/sync.context";
-import {
-  importGCalSlice,
-  triggerFetch,
-} from "@web/ducks/events/slices/sync.slice";
+import { triggerFetch } from "@web/ducks/events/slices/sync.slice";
+import { useAppDispatch } from "@web/store/store.hooks";
 import { sseEmitter } from "../client/sse.client";
 
 export const useGcalSSE = () => {
-  const dispatch = useDispatch();
+  const dispatch = useAppDispatch();
 
   const onImportEnd = useCallback(
     (payload?: ImportGCalEndPayload) => {
-      if (payload?.operation === "REPAIR") {
-        dispatch(importGCalSlice.actions.stopRepair());
-      }
-      void refreshUserMetadata();
+      clearGoogleSyncIndicatorOverride();
 
       if (payload?.status === "ERRORED") {
-        dispatch(importGCalSlice.actions.setImportError(payload.message));
+        void refreshUserMetadata();
         if (payload.operation === "REPAIR") {
           showErrorToast(payload.message, {
             toastId: GOOGLE_REPAIR_FAILED_TOAST_ID,
@@ -40,18 +40,11 @@ export const useGcalSSE = () => {
       }
 
       if (payload?.status === "IGNORED") {
+        void refreshUserMetadata();
         return;
       }
 
-      if (payload?.status === "COMPLETED") {
-        dispatch(
-          importGCalSlice.actions.setImportResults({
-            eventsCount: payload.eventsCount,
-            calendarsCount: payload.calendarsCount,
-          }),
-        );
-      }
-
+      void refreshUserMetadata();
       dispatch(
         triggerFetch({
           reason: Sync_AsyncStateContextReason.IMPORT_COMPLETE,
@@ -61,25 +54,22 @@ export const useGcalSSE = () => {
     [dispatch],
   );
 
+  const onImportStart = useCallback(() => {
+    if (getGoogleSyncIndicatorOverride() !== null) {
+      return;
+    }
+
+    setSyncingSyncIndicatorOverride();
+  }, []);
+
   const onGoogleRevoked = useCallback(() => {
-    dispatch(importGCalSlice.actions.stopRepair());
+    clearGoogleSyncIndicatorOverride();
     handleGoogleRevoked();
-  }, [dispatch]);
+  }, []);
 
   const onMetadataFetch = useCallback(
     (metadata: UserMetadata) => {
-      const importStatus = metadata.sync?.importGCal;
-      const connectionState = metadata.google?.connectionState;
-      const shouldAutoImport =
-        importStatus === "RESTART" &&
-        connectionState !== "RECONNECT_REQUIRED" &&
-        connectionState !== "NOT_CONNECTED";
-
       dispatch(userMetadataSlice.actions.set(metadata));
-
-      if (shouldAutoImport) {
-        dispatch(importGCalSlice.actions.request());
-      }
     },
     [dispatch],
   );
@@ -92,6 +82,10 @@ export const useGcalSSE = () => {
       onImportEnd(payload);
     };
 
+    const importStartHandler = () => {
+      onImportStart();
+    };
+
     const googleRevokedHandler = () => {
       onGoogleRevoked();
     };
@@ -103,14 +97,16 @@ export const useGcalSSE = () => {
       onMetadataFetch(metadata);
     };
 
+    sseEmitter.on(IMPORT_GCAL_START, importStartHandler);
     sseEmitter.on(IMPORT_GCAL_END, importEndHandler);
     sseEmitter.on(GOOGLE_REVOKED, googleRevokedHandler);
     sseEmitter.on(USER_METADATA, userMetadataHandler);
 
     return () => {
+      sseEmitter.off(IMPORT_GCAL_START, importStartHandler);
       sseEmitter.off(IMPORT_GCAL_END, importEndHandler);
       sseEmitter.off(GOOGLE_REVOKED, googleRevokedHandler);
       sseEmitter.off(USER_METADATA, userMetadataHandler);
     };
-  }, [onImportEnd, onGoogleRevoked, onMetadataFetch]);
+  }, [onImportEnd, onImportStart, onGoogleRevoked, onMetadataFetch]);
 };
diff --git a/packages/web/src/sse/hooks/useSSEConnection.ts b/packages/web/src/sse/hooks/useSSEConnection.ts
index a14246bc1..3238a4c6e 100644
--- a/packages/web/src/sse/hooks/useSSEConnection.ts
+++ b/packages/web/src/sse/hooks/useSSEConnection.ts
@@ -1,15 +1,17 @@
 import { useEffect } from "react";
-import { useUser } from "@web/auth/hooks/user/useUser";
+import { useSession } from "@web/auth/compass/session/useSession";
+import { useUser } from "@web/auth/compass/user/hooks/useUser";
 import { closeStream, openStream } from "../client/sse.client";
 
 export const useSSEConnection = () => {
+  const { authenticated } = useSession();
   const { userId } = useUser();
 
   useEffect(() => {
-    if (userId) {
+    if (authenticated || userId) {
       openStream();
     } else {
       closeStream();
     }
-  }, [userId]);
+  }, [authenticated, userId]);
 };
diff --git a/packages/web/src/sse/provider/SSEProvider.interaction.test.tsx b/packages/web/src/sse/provider/SSEProvider.interaction.test.tsx
index e9f3f9b25..ea1e8209b 100644
--- a/packages/web/src/sse/provider/SSEProvider.interaction.test.tsx
+++ b/packages/web/src/sse/provider/SSEProvider.interaction.test.tsx
@@ -1,39 +1,36 @@
 import { type EventEmitter2 } from "eventemitter2";
 import { act } from "react";
 import { Provider } from "react-redux";
+import { combineReducers, configureStore } from "@reduxjs/toolkit";
+import { render, waitFor } from "@testing-library/react";
 import {
-  type EnhancedStore,
-  combineReducers,
-  configureStore,
-} from "@reduxjs/toolkit";
-import "@testing-library/jest-dom";
-import { render, screen, waitFor } from "@testing-library/react";
-import { IMPORT_GCAL_END } from "@core/constants/sse.constants";
+  GOOGLE_REVOKED,
+  IMPORT_GCAL_END,
+  IMPORT_GCAL_START,
+  USER_METADATA,
+} from "@core/constants/sse.constants";
 import { type ImportGCalEndPayload } from "@core/types/sse.types";
-import { SyncEventsOverlay } from "@web/components/SyncEventsOverlay/SyncEventsOverlay";
-import { authSlice } from "@web/ducks/auth/slices/auth.slice";
+import { type UserMetadata } from "@core/types/user.types";
 import {
-  importGCalSlice,
-  importLatestSlice,
-} from "@web/ducks/events/slices/sync.slice";
-import SSEProvider from "./SSEProvider";
-
-type TestStore = EnhancedStore<{
-  sync: {
-    importGCal: ReturnType<typeof importGCalSlice.reducer>;
-    importLatest: ReturnType<typeof importLatestSlice.reducer>;
-  };
-  auth: ReturnType<typeof authSlice.reducer>;
-}>;
-
-// Mock dependencies
-jest.mock("@web/auth/hooks/user/useUser", () => ({
-  useUser: () => ({ userId: "test-user-id" }),
+  getGoogleSyncIndicatorOverride,
+  resetGoogleSyncUIStateForTests,
+  setRepairingSyncIndicatorOverride,
+} from "@web/auth/google/state/google.sync.state";
+import { handleGoogleRevoked } from "@web/auth/google/util/google.auth.util";
+import { showErrorToast } from "@web/common/utils/toast/error-toast.util";
+import { userMetadataSlice } from "@web/ducks/auth/slices/user-metadata.slice";
+import { importLatestSlice } from "@web/ducks/events/slices/sync.slice";
+import { useGcalSSE } from "../hooks/useGcalSSE";
+
+jest.mock("@web/auth/google/util/google.auth.util", () => ({
+  handleGoogleRevoked: jest.fn(),
 }));
-jest.mock("@web/auth/session/user-metadata.util", () => ({
+jest.mock("@web/auth/compass/user/util/user-metadata.util", () => ({
   refreshUserMetadata: jest.fn().mockResolvedValue(undefined),
 }));
-
+jest.mock("@web/common/utils/toast/error-toast.util", () => ({
+  showErrorToast: jest.fn(),
+}));
 jest.mock("../client/sse.client", () => {
   // eslint-disable-next-line @typescript-eslint/no-require-imports, @typescript-eslint/no-unsafe-assignment
   const { EventEmitter2 } = require("eventemitter2");
@@ -47,244 +44,189 @@ jest.mock("../client/sse.client", () => {
   };
 });
 
-function fireImportEnd(payload: ImportGCalEndPayload) {
+const mockHandleGoogleRevoked = handleGoogleRevoked as jest.MockedFunction<
+  typeof handleGoogleRevoked
+>;
+const mockShowErrorToast = showErrorToast as jest.MockedFunction<
+  typeof showErrorToast
+>;
+
+const HookHost = () => {
+  useGcalSSE();
+  return null;
+};
+
+const getSseEmitter = () => {
   // eslint-disable-next-line @typescript-eslint/no-require-imports
-  const { sseEmitter } = require("../client/sse.client") as {
-    sseEmitter: EventEmitter2;
-  };
-  sseEmitter.emit(
+  return (require("../client/sse.client") as { sseEmitter: EventEmitter2 })
+    .sseEmitter;
+};
+
+const fireImportStart = () => {
+  getSseEmitter().emit(IMPORT_GCAL_START, new MessageEvent(IMPORT_GCAL_START));
+};
+
+const fireImportEnd = (payload: ImportGCalEndPayload) => {
+  getSseEmitter().emit(
     IMPORT_GCAL_END,
     new MessageEvent(IMPORT_GCAL_END, { data: JSON.stringify(payload) }),
   );
-}
-
-/**
- * Integration tests for the Google Calendar authentication and import flow.
- *
- * These tests validate the complete user experience, ensuring:
- * - OAuth popup blocks the app with "Complete Google sign-in" overlay
- * - Import runs in background with sidebar spinner (non-blocking)
- * - Overlay disappears immediately after OAuth completes
- */
-describe("GCal Authentication Flow", () => {
-  const createTestStore = (preloadedState?: {
-    isAuthenticating?: boolean;
-  }): TestStore => {
-    return configureStore({
+};
+
+const fireUserMetadata = (metadata: UserMetadata) => {
+  getSseEmitter().emit(
+    USER_METADATA,
+    new MessageEvent(USER_METADATA, { data: JSON.stringify(metadata) }),
+  );
+};
+
+describe("useGcalSSE", () => {
+  const createStore = () =>
+    configureStore({
       reducer: {
         sync: combineReducers({
-          importGCal: importGCalSlice.reducer,
           importLatest: importLatestSlice.reducer,
         }),
-        auth: authSlice.reducer,
-      },
-      preloadedState: {
-        sync: {
-          importGCal: {
-            isRepairing: false,
-            importResults: null,
-            pendingLocalEventsSynced: null,
-            importError: null,
-            isLoading: false,
-            value: undefined,
-            error: undefined,
-          },
-          importLatest: {
-            isFetchNeeded: false,
-            reason: null,
-          },
-        },
-        auth: {
-          status: preloadedState?.isAuthenticating ? "authenticating" : "idle",
-          error: null,
-        },
+        userMetadata: userMetadataSlice.reducer,
       },
     });
-  };
 
   beforeEach(() => {
     jest.clearAllMocks();
-    jest.useFakeTimers();
-    document.body.removeAttribute("data-app-locked");
-  });
-
-  afterEach(() => {
-    jest.useRealTimers();
-    document.body.removeAttribute("data-app-locked");
+    resetGoogleSyncUIStateForTests();
   });
 
-  describe("OAuth phase (blocking)", () => {
-    it("shows blocking overlay during OAuth popup", () => {
-      const store = createTestStore({ isAuthenticating: true });
+  it("does not trigger a client-side import when USER_METADATA reports RESTART", () => {
+    const store = createStore();
 
-      render(
-        <Provider store={store}>
-          <SSEProvider>
-            <SyncEventsOverlay />
-          </SSEProvider>
-        </Provider>,
-      );
+    render(
+      <Provider store={store}>
+        <HookHost />
+      </Provider>,
+    );
 
-      expect(
-        screen.getByText("Complete Google sign-in..."),
-      ).toBeInTheDocument();
-      expect(
-        screen.getByText("Please complete authorization in the popup window"),
-      ).toBeInTheDocument();
-      expect(document.body).toHaveAttribute("data-app-locked", "true");
+    act(() => {
+      fireUserMetadata({
+        google: { connectionState: "ATTENTION" },
+        sync: { importGCal: "RESTART" },
+      });
     });
 
-    it("dismisses overlay immediately when OAuth completes", () => {
-      const store = createTestStore({ isAuthenticating: true });
+    expect(store.getState().userMetadata.current).toEqual({
+      google: { connectionState: "ATTENTION" },
+      sync: { importGCal: "RESTART" },
+    });
+  });
 
-      const { rerender, container } = render(
-        <Provider store={store}>
-          <SSEProvider>
-            <SyncEventsOverlay />
-          </SSEProvider>
-        </Provider>,
-      );
+  it("stores IMPORTING metadata without starting another import", () => {
+    const store = createStore();
 
-      expect(
-        screen.getByText("Complete Google sign-in..."),
-      ).toBeInTheDocument();
+    render(
+      <Provider store={store}>
+        <HookHost />
+      </Provider>,
+    );
 
-      // OAuth completes (auth state resets)
-      act(() => {
-        store.dispatch(authSlice.actions.resetAuth());
-      });
-
-      rerender(
-        <Provider store={store}>
-          <SSEProvider>
-            <SyncEventsOverlay />
-          </SSEProvider>
-        </Provider>,
-      );
-
-      // Wait for buffered visibility to settle
-      act(() => {
-        jest.advanceTimersByTime(100);
+    act(() => {
+      fireUserMetadata({
+        google: { connectionState: "IMPORTING" },
+        sync: { importGCal: "IMPORTING" },
       });
+    });
 
-      // Overlay should be dismissed
-      expect(
-        screen.queryByText("Complete Google sign-in..."),
-      ).not.toBeInTheDocument();
-      expect(container).toBeEmptyDOMElement();
-      expect(document.body).not.toHaveAttribute("data-app-locked");
+    expect(store.getState().userMetadata.current).toEqual({
+      google: { connectionState: "IMPORTING" },
+      sync: { importGCal: "IMPORTING" },
     });
   });
 
-  describe("Import phase (non-blocking)", () => {
-    it("does not show blocking overlay when not authenticating", () => {
-      const store = createTestStore();
+  it("sets the syncing override when IMPORT_GCAL_START arrives", async () => {
+    const store = createStore();
 
-      const { container } = render(
-        <Provider store={store}>
-          <SSEProvider>
-            <SyncEventsOverlay />
-          </SSEProvider>
-        </Provider>,
-      );
+    render(
+      <Provider store={store}>
+        <HookHost />
+      </Provider>,
+    );
 
-      act(() => {
-        jest.advanceTimersByTime(100);
-      });
+    act(() => {
+      fireImportStart();
+    });
 
-      // No blocking overlay should be shown
-      expect(container).toBeEmptyDOMElement();
-      expect(document.body).not.toHaveAttribute("data-app-locked");
+    await waitFor(() => {
+      expect(getGoogleSyncIndicatorOverride()).toBe("syncing");
     });
   });
 
-  describe("Complete authentication flow", () => {
-    it("handles OAuth → import transition without stale state", async () => {
-      // Start with OAuth in progress
-      const store = createTestStore({ isAuthenticating: true });
-
-      const { rerender, container } = render(
-        <Provider store={store}>
-          <SSEProvider>
-            <SyncEventsOverlay />
-          </SSEProvider>
-        </Provider>,
-      );
-
-      // Phase 1: OAuth in progress
-      expect(
-        screen.getByText("Complete Google sign-in..."),
-      ).toBeInTheDocument();
-
-      // OAuth completes, auth state resets
-      act(() => {
-        store.dispatch(authSlice.actions.resetAuth());
+  it("clears the syncing override and triggers refetch after REPAIR completion", async () => {
+    const store = createStore();
+    setRepairingSyncIndicatorOverride();
+
+    render(
+      <Provider store={store}>
+        <HookHost />
+      </Provider>,
+    );
+
+    act(() => {
+      fireImportEnd({
+        operation: "REPAIR",
+        status: "COMPLETED",
+        eventsCount: 4,
+        calendarsCount: 1,
       });
+    });
 
-      rerender(
-        <Provider store={store}>
-          <SSEProvider>
-            <SyncEventsOverlay />
-          </SSEProvider>
-        </Provider>,
-      );
-
-      act(() => {
-        jest.advanceTimersByTime(100);
-      });
+    await waitFor(() => {
+      expect(getGoogleSyncIndicatorOverride()).toBe(null);
+      expect(store.getState().sync.importLatest.isFetchNeeded).toBe(true);
+    });
+  });
 
-      // Phase 2: Overlay should be dismissed (import runs in background)
-      expect(
-        screen.queryByText("Complete Google sign-in..."),
-      ).not.toBeInTheDocument();
-      expect(container).toBeEmptyDOMElement();
-
-      // Backend completes import
-      act(() => {
-        fireImportEnd({
-          operation: "REPAIR",
-          status: "COMPLETED",
-          eventsCount: 42,
-          calendarsCount: 2,
-        });
+  it("clears the syncing override and shows the repair toast after REPAIR failure", async () => {
+    const store = createStore();
+    setRepairingSyncIndicatorOverride();
+
+    render(
+      <Provider store={store}>
+        <HookHost />
+      </Provider>,
+    );
+
+    act(() => {
+      fireImportEnd({
+        operation: "REPAIR",
+        status: "ERRORED",
+        message: "Google Calendar repair failed",
       });
+    });
 
-      // Verify final state
-      const state = store.getState();
-      expect(state.sync.importGCal.importResults).toEqual({
-        eventsCount: 42,
-        calendarsCount: 2,
-      });
-      expect(state.sync.importLatest.isFetchNeeded).toBe(true);
+    await waitFor(() => {
+      expect(getGoogleSyncIndicatorOverride()).toBe(null);
+      expect(mockShowErrorToast).toHaveBeenCalledWith(
+        "Google Calendar repair failed",
+        expect.anything(),
+      );
     });
   });
 
-  describe("Error handling", () => {
-    it("handles import errors gracefully", async () => {
-      const store = createTestStore({});
+  it("clears the syncing override when Google is revoked", async () => {
+    const store = createStore();
+    setRepairingSyncIndicatorOverride();
 
-      render(
-        <Provider store={store}>
-          <SSEProvider>
-            <SyncEventsOverlay />
-          </SSEProvider>
-        </Provider>,
-      );
+    render(
+      <Provider store={store}>
+        <HookHost />
+      </Provider>,
+    );
 
-      act(() => {
-        fireImportEnd({
-          operation: "INCREMENTAL",
-          status: "ERRORED",
-          message:
-            "Incremental Google Calendar sync failed for user: test-user",
-        });
-      });
+    act(() => {
+      getSseEmitter().emit(GOOGLE_REVOKED, new MessageEvent(GOOGLE_REVOKED));
+    });
 
-      await waitFor(() => {
-        expect(store.getState().sync.importGCal.importError).toBe(
-          "Incremental Google Calendar sync failed for user: test-user",
-        );
-      });
+    await waitFor(() => {
+      expect(getGoogleSyncIndicatorOverride()).toBe(null);
+      expect(mockHandleGoogleRevoked).toHaveBeenCalledTimes(1);
     });
   });
 });
diff --git a/packages/web/src/sse/provider/SSEProvider.test.tsx b/packages/web/src/sse/provider/SSEProvider.test.tsx
index bbed672a9..9c2bef334 100644
--- a/packages/web/src/sse/provider/SSEProvider.test.tsx
+++ b/packages/web/src/sse/provider/SSEProvider.test.tsx
@@ -1,26 +1,22 @@
 import { type EventEmitter2 } from "eventemitter2";
-import { act } from "react";
 import { Provider } from "react-redux";
 import { combineReducers, configureStore } from "@reduxjs/toolkit";
 import { render, waitFor } from "@testing-library/react";
-import { IMPORT_GCAL_END } from "@core/constants/sse.constants";
-import { type ImportGCalEndPayload } from "@core/types/sse.types";
-import { useUser } from "@web/auth/hooks/user/useUser";
-import {
-  importGCalSlice,
-  importLatestSlice,
-} from "@web/ducks/events/slices/sync.slice";
+import { useSession } from "@web/auth/compass/session/useSession";
+import { useUser } from "@web/auth/compass/user/hooks/useUser";
+import { importLatestSlice } from "@web/ducks/events/slices/sync.slice";
 import SSEProvider from "./SSEProvider";
 
-// Mock dependencies
-jest.mock("@web/auth/hooks/user/useUser");
-jest.mock("@web/auth/session/user-metadata.util", () => ({
+jest.mock("@web/auth/compass/session/useSession");
+jest.mock("@web/auth/compass/user/hooks/useUser");
+jest.mock("@web/auth/compass/user/util/user-metadata.util", () => ({
   refreshUserMetadata: jest.fn().mockResolvedValue(undefined),
 }));
 jest.mock("../client/sse.client", () => {
-  // eslint-disable-next-line @typescript-eslint/no-require-imports
-  const { EventEmitter2 } = require("eventemitter2");
-  // eslint-disable-next-line @typescript-eslint/no-unsafe-call
+  const eventEmitterModule: {
+    EventEmitter2: new (options?: { maxListeners?: number }) => EventEmitter2;
+  } = jest.requireActual("eventemitter2");
+  const { EventEmitter2 } = eventEmitterModule;
   const sseEmitter = new EventEmitter2({ maxListeners: 20 });
   return {
     openStream: jest.fn(),
@@ -30,61 +26,47 @@ jest.mock("../client/sse.client", () => {
   };
 });
 
+const mockUseSession = useSession as jest.MockedFunction<typeof useSession>;
 const mockUseUser = useUser as jest.MockedFunction<typeof useUser>;
 
 describe("SSEProvider", () => {
-  const mockUserId = "test-user-id";
-
   beforeEach(() => {
     jest.clearAllMocks();
-    mockUseUser.mockReturnValue({ userId: mockUserId });
+    mockUseSession.mockReturnValue({
+      authenticated: true,
+      setAuthenticated: jest.fn(),
+    });
+    mockUseUser.mockReturnValue({ userId: "test-user-id" });
   });
 
-  it("sets import results and triggers refetch on import completion", async () => {
+  it("keeps the SSE stream open while authenticated even before the user id loads", async () => {
+    mockUseUser.mockReturnValue({ userId: undefined });
+
     // eslint-disable-next-line @typescript-eslint/no-require-imports
-    const { sseEmitter } = require("../client/sse.client") as {
-      sseEmitter: EventEmitter2;
+    const { closeStream, openStream } = require("../client/sse.client") as {
+      closeStream: jest.Mock;
+      openStream: jest.Mock;
     };
 
-    const store = configureStore({
-      reducer: {
-        sync: combineReducers({
-          importGCal: importGCalSlice.reducer,
-          importLatest: importLatestSlice.reducer,
-        }),
-      },
-    });
-
     render(
-      <Provider store={store}>
+      <Provider
+        store={configureStore({
+          reducer: {
+            sync: combineReducers({
+              importLatest: importLatestSlice.reducer,
+            }),
+          },
+        })}
+      >
         <SSEProvider>
           <div>Test</div>
         </SSEProvider>
       </Provider>,
     );
 
-    const payload: ImportGCalEndPayload = {
-      operation: "REPAIR",
-      status: "COMPLETED",
-      eventsCount: 10,
-      calendarsCount: 2,
-    };
-
-    act(() => {
-      sseEmitter.emit(
-        IMPORT_GCAL_END,
-        new MessageEvent(IMPORT_GCAL_END, { data: JSON.stringify(payload) }),
-      );
-    });
-
     await waitFor(() => {
-      const state = store.getState();
-      expect(state.sync.importGCal.importResults).toEqual({
-        eventsCount: 10,
-        calendarsCount: 2,
-      });
+      expect(openStream).toHaveBeenCalled();
     });
-
-    expect(store.getState().sync.importLatest.isFetchNeeded).toBe(true);
+    expect(closeStream).not.toHaveBeenCalled();
   });
 });
diff --git a/packages/web/src/store/reducers.ts b/packages/web/src/store/reducers.ts
index 2fad00451..1daef2ec2 100644
--- a/packages/web/src/store/reducers.ts
+++ b/packages/web/src/store/reducers.ts
@@ -12,10 +12,7 @@ import {
 } from "@web/ducks/events/slices/event.slice";
 import { pendingEventsSlice } from "@web/ducks/events/slices/pending.slice";
 import { getSomedayEventsSlice } from "@web/ducks/events/slices/someday.slice";
-import {
-  importGCalSlice,
-  importLatestSlice,
-} from "@web/ducks/events/slices/sync.slice";
+import { importLatestSlice } from "@web/ducks/events/slices/sync.slice";
 import { viewSlice } from "@web/ducks/events/slices/view.slice";
 import { getWeekEventsSlice } from "@web/ducks/events/slices/week.slice";
 import { settingsSlice } from "@web/ducks/settings/slices/settings.slice";
@@ -34,7 +31,6 @@ const eventsReducer = combineReducers({
 });
 
 const syncReducer = combineReducers({
-  importGCal: importGCalSlice.reducer,
   importLatest: importLatestSlice.reducer,
 });
 
diff --git a/packages/web/src/store/sagas.ts b/packages/web/src/store/sagas.ts
index 771911b60..0f792277a 100644
--- a/packages/web/src/store/sagas.ts
+++ b/packages/web/src/store/sagas.ts
@@ -14,7 +14,6 @@ import {
   getSomedayEvents,
   reorderSomedayEvents,
 } from "@web/ducks/events/sagas/someday.sagas";
-import { importGCal } from "@web/ducks/events/sagas/sync.sagas";
 import { getDayEventsSlice } from "@web/ducks/events/slices/day.slice";
 import {
   createEventSlice,
@@ -23,11 +22,10 @@ import {
   getCurrentMonthEventsSlice,
 } from "@web/ducks/events/slices/event.slice";
 import { getSomedayEventsSlice } from "@web/ducks/events/slices/someday.slice";
-import { importGCalSlice } from "@web/ducks/events/slices/sync.slice";
 import { getWeekEventsSlice } from "@web/ducks/events/slices/week.slice";
 
 export function* sagas() {
-  yield all([eventSagas(), somedayEventSagas(), syncSagas()]);
+  yield all([eventSagas(), somedayEventSagas()]);
 }
 
 function* eventSagas() {
@@ -55,7 +53,3 @@ function* somedayEventSagas() {
   yield takeLatest(getSomedayEventsSlice.actions.delete, deleteSomedayEvent);
   yield takeLatest(getSomedayEventsSlice.actions.reorder, reorderSomedayEvents);
 }
-
-function* syncSagas() {
-  yield takeLatest(importGCalSlice.actions.request, importGCal);
-}
diff --git a/packages/web/src/views/Calendar/Calendar.form.test.tsx b/packages/web/src/views/Calendar/Calendar.form.test.tsx
index 671103c44..ed2d6da86 100644
--- a/packages/web/src/views/Calendar/Calendar.form.test.tsx
+++ b/packages/web/src/views/Calendar/Calendar.form.test.tsx
@@ -48,7 +48,7 @@ jest.mock("@web/common/utils/dom/event-target-visibility.util", () => ({
     },
 }));
 
-jest.mock("@web/auth/session/session.util", () => ({
+jest.mock("@web/auth/compass/session/session.util", () => ({
   getUserId: async () => "test-user-id",
 }));
 
diff --git a/packages/web/src/views/Calendar/components/Draft/sidebar/hooks/useSidebarActions.ts b/packages/web/src/views/Calendar/components/Draft/sidebar/hooks/useSidebarActions.ts
index 1b541b8ea..d43c4128e 100644
--- a/packages/web/src/views/Calendar/components/Draft/sidebar/hooks/useSidebarActions.ts
+++ b/packages/web/src/views/Calendar/components/Draft/sidebar/hooks/useSidebarActions.ts
@@ -13,7 +13,7 @@ import {
   type Schema_Event,
 } from "@core/types/event.types";
 import dayjs from "@core/util/date/dayjs";
-import { getUserId } from "@web/auth/session/session.util";
+import { getUserId } from "@web/auth/compass/session/session.util";
 import {
   COLUMN_MONTH,
   type COLUMN_WEEK,
diff --git a/packages/web/src/views/Calendar/components/Header/DayLabels.tsx b/packages/web/src/views/Calendar/components/Header/DayLabels.tsx
index 95558b425..89d8e0fe0 100644
--- a/packages/web/src/views/Calendar/components/Header/DayLabels.tsx
+++ b/packages/web/src/views/Calendar/components/Header/DayLabels.tsx
@@ -1,11 +1,9 @@
-import React, { type FC } from "react";
+import { type FC } from "react";
 import { type Dayjs } from "@core/util/date/dayjs";
 import { theme } from "@web/common/styles/theme";
 import { getWeekDayLabel } from "@web/common/utils/event/event.util";
-import { AlignItems, JustifyContent } from "@web/components/Flex/styled";
 import { SpaceCharacter } from "@web/components/SpaceCharacter";
 import { Text } from "@web/components/Text";
-import { StyledWeekDayFlex, StyledWeekDaysFlex } from "./styled";
 
 interface Props {
   today: Dayjs;
@@ -44,27 +42,26 @@ export const DayLabels: FC<Props> = ({
   };
 
   return (
-    <StyledWeekDaysFlex>
+    <div className="mt-[10px] flex w-full">
       {weekDays.map((day) => {
         const dayNumber = getDayNumber(day);
         const { isToday, color } = getColor(day);
 
         return (
-          <StyledWeekDayFlex
-            justifyContent={JustifyContent.CENTER}
+          <div
+            className="flex min-w-[100px] basis-full items-end justify-center"
             key={getWeekDayLabel(day)}
-            alignItems={AlignItems.FLEX_END}
+            style={{ color }}
             title={getWeekDayLabel(day)}
-            color={color}
           >
             <Text size="xxl" withGradient={isToday}>
               {dayNumber}
             </Text>
             <SpaceCharacter />
             <Text size="l">{day.format("ddd")}</Text>
-          </StyledWeekDayFlex>
+          </div>
         );
       })}
-    </StyledWeekDaysFlex>
+    </div>
   );
 };
diff --git a/packages/web/src/views/Calendar/components/Header/Header.tsx b/packages/web/src/views/Calendar/components/Header/Header.tsx
index de2886b9d..66d45e034 100644
--- a/packages/web/src/views/Calendar/components/Header/Header.tsx
+++ b/packages/web/src/views/Calendar/components/Header/Header.tsx
@@ -2,8 +2,7 @@ import { type FC } from "react";
 import dayjs, { type Dayjs } from "@core/util/date/dayjs";
 import { theme } from "@web/common/styles/theme";
 import { getCalendarHeadingLabel } from "@web/common/utils/datetime/web.date.util";
-import { AccountIcon } from "@web/components/AuthModal/AccountIcon";
-import { AlignItems } from "@web/components/Flex/styled";
+import { HeaderInfoIcon } from "@web/components/HeaderInfoIcon/HeaderInfoIcon";
 import { SidebarIcon } from "@web/components/Icons/Sidebar";
 import { SelectView } from "@web/components/SelectView/SelectView";
 import { Text } from "@web/components/Text";
@@ -16,15 +15,6 @@ import { type Util_Scroll } from "../../hooks/grid/useScroll";
 import { type WeekProps } from "../../hooks/useWeek";
 import { TodayButton } from "../TodayButton/TodayButton";
 import { DayLabels } from "./DayLabels";
-import {
-  ArrowNavigationButton,
-  StyledHeaderLabel,
-  StyledHeaderRow,
-  StyledLeftGroup,
-  StyledNavigationArrows,
-  StyledNavigationGroup,
-  StyledRightGroup,
-} from "./styled";
 
 interface Props {
   rootProps: RootProps;
@@ -52,7 +42,7 @@ export const Header: FC<Props> = ({ scrollUtil, today, weekProps }) => {
 
   return (
     <>
-      <StyledHeaderRow alignItems={AlignItems.BASELINE}>
+      <div className="text-text-light relative flex h-20 w-full items-baseline justify-between">
         <TooltipWrapper
           description={isSidebarOpen ? "Close sidebar" : "Open sidebar"}
           onClick={() => dispatch(viewSlice.actions.toggleSidebar())}
@@ -66,53 +56,55 @@ export const Header: FC<Props> = ({ scrollUtil, today, weekProps }) => {
             }
           />
         </TooltipWrapper>
-        <StyledLeftGroup>
-          <StyledHeaderLabel aria-level={1} role="heading">
+        <div className="z-[2] flex items-center justify-between">
+          <div aria-level={1} className="text-text-light pl-5" role="heading">
             <Text size="xl">{headerLabel}</Text>
-          </StyledHeaderLabel>
-        </StyledLeftGroup>
-        <StyledRightGroup>
-          <AccountIcon />
+          </div>
+        </div>
+        <div className="z-[2] flex h-full items-center justify-between">
+          <HeaderInfoIcon />
           <SelectView />
           <div>
-            <StyledNavigationGroup>
+            <div className="mr-5 flex items-center justify-between">
               <TodayButton
                 navigateToToday={onTodayClick}
                 isToday={weekProps.component.isCurrentWeek}
               />
-              <StyledNavigationArrows>
+              <div className="flex items-center gap-3 pl-5">
                 <TooltipWrapper
                   onClick={() => weekProps.util.decrementWeek()}
                   shortcut="J"
                 >
-                  <ArrowNavigationButton
+                  <Text
+                    className="flex h-[30px] w-[30px] items-center justify-center transition-[filter] duration-[350ms] ease-out select-none hover:rounded-full hover:brightness-[1.6]"
                     cursor="pointer"
                     role="navigation"
                     size="xxl"
                     title="previous week"
                   >
                     {"<"}
-                  </ArrowNavigationButton>
+                  </Text>
                 </TooltipWrapper>
 
                 <TooltipWrapper
                   onClick={() => weekProps.util.incrementWeek()}
                   shortcut="K"
                 >
-                  <ArrowNavigationButton
+                  <Text
+                    className="flex h-[30px] w-[30px] items-center justify-center transition-[filter] duration-[350ms] ease-out select-none hover:rounded-full hover:brightness-[1.6]"
                     cursor="pointer"
                     role="navigation"
                     size="xxl"
                     title="next week"
                   >
                     {">"}
-                  </ArrowNavigationButton>
+                  </Text>
                 </TooltipWrapper>
-              </StyledNavigationArrows>
-            </StyledNavigationGroup>
+              </div>
+            </div>
           </div>
-        </StyledRightGroup>
-      </StyledHeaderRow>
+        </div>
+      </div>
 
       <DayLabels
         startOfView={weekProps.component.startOfView}
diff --git a/packages/web/src/views/Calendar/components/Header/styled.ts b/packages/web/src/views/Calendar/components/Header/styled.ts
deleted file mode 100644
index 3aa3d9878..000000000
--- a/packages/web/src/views/Calendar/components/Header/styled.ts
+++ /dev/null
@@ -1,104 +0,0 @@
-import styled from "styled-components";
-import { ZIndex } from "@web/common/constants/web.constants";
-import { c } from "@web/common/styles/colors";
-import { Flex } from "@web/components/Flex";
-import { JustifyContent } from "@web/components/Flex/styled";
-import { Text } from "@web/components/Text";
-
-// Constants
-export const HEADER_HEIGHT = 80;
-export const GRID_MARGIN_LEFT = 60;
-export const WEEK_DAYS_MARGIN_Y = 10;
-export const EVENT_WIDTH_MINIMUM = 100;
-
-// Header components
-export const StyledHeaderRow = styled(Flex)`
-  color: ${c.gray100};
-  font-size: 40px;
-  justify-content: ${JustifyContent.SPACE_BETWEEN};
-  height: ${HEADER_HEIGHT}px;
-  width: 100%;
-  position: relative;
-  align-items: center;
-`;
-
-export const StyledLeftGroup = styled(Flex)`
-  align-items: center;
-  justify-content: space-between;
-  z-index: ${ZIndex.LAYER_2};
-`;
-
-export const StyledRightGroup = styled(Flex)`
-  align-items: center;
-  flex-direction: row;
-  justify-content: space-between;
-  height: 100%;
-  z-index: ${ZIndex.LAYER_2};
-`;
-
-export const StyledHeaderLabel = styled(Flex)`
-  padding-left: 20px;
-  color: ${c.gray100};
-`;
-
-export const StyledNavigationGroup = styled(Flex)`
-  align-items: center;
-  justify-content: space-between;
-  margin-right: 20px;
-`;
-
-export const StyledNavigationArrows = styled(Flex)`
-  padding-left: 20px;
-  align-items: center;
-`;
-
-export const ArrowNavigationButton = styled(Text)`
-  display: flex;
-  justify-content: center;
-  height: 30px;
-  user-select: none;
-  width: 30px;
-
-  &:hover {
-    border-radius: 50%;
-    filter: brightness(160%);
-    transition: filter 0.35s ease-out;
-  }
-
-  &:first-child {
-    margin-right: 12px;
-  }
-`;
-
-// Week days components
-export const StyledWeekDaysFlex = styled(Flex)`
-  width: 100%;
-  margin: ${WEEK_DAYS_MARGIN_Y}px 0 0 0;
-  /* margin-left: ${GRID_MARGIN_LEFT}px; */
-`;
-
-export const StyledWeekDayFlex = styled(Flex)<{ color: string }>`
-  color: ${({ color }) => color};
-  flex-basis: 100%;
-  min-width: ${EVENT_WIDTH_MINIMUM}px;
-`;
-
-export const StyledMonthLabel = styled(Text)`
-  font-size: 24px;
-  color: ${c.gray100};
-  margin-left: 20px;
-`;
-
-// Today button
-export const StyledTodayButton = styled.button`
-  background: transparent;
-  color: ${c.gray100};
-  border-radius: 4px;
-  padding: 4px 8px;
-  cursor: pointer;
-  font-size: 14px;
-
-  &:hover {
-    background: rgba(255, 255, 255, 0.1);
-  }
-`;
diff --git a/packages/web/src/views/Calendar/components/Sidebar/MonthTab/SubCalendarList/SubCalendarList.test.tsx b/packages/web/src/views/Calendar/components/Sidebar/MonthTab/SubCalendarList/SubCalendarList.test.tsx
new file mode 100644
index 000000000..65f5acbfe
--- /dev/null
+++ b/packages/web/src/views/Calendar/components/Sidebar/MonthTab/SubCalendarList/SubCalendarList.test.tsx
@@ -0,0 +1,94 @@
+import "@testing-library/jest-dom";
+import { render, screen, waitFor } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
+import { useUser } from "@web/auth/compass/user/hooks/useUser";
+import { useAuthModal } from "@web/components/AuthModal/hooks/useAuthModal";
+import { SubCalendarList } from "./SubCalendarList";
+
+jest.mock("@web/auth/compass/user/hooks/useUser", () => ({
+  useUser: jest.fn(),
+}));
+
+jest.mock("@web/components/AuthModal/hooks/useAuthModal", () => ({
+  useAuthModal: jest.fn(),
+}));
+
+const mockUseUser = useUser as jest.MockedFunction<typeof useUser>;
+const mockUseAuthModal = useAuthModal as jest.MockedFunction<
+  typeof useAuthModal
+>;
+
+describe("SubCalendarList", () => {
+  const openModal = jest.fn();
+
+  beforeEach(() => {
+    openModal.mockReset();
+    mockUseAuthModal.mockReturnValue({
+      closeModal: jest.fn(),
+      currentView: "login",
+      isOpen: false,
+      openModal,
+      setView: jest.fn(),
+    });
+  });
+
+  it("renders the signed in email without the temporary account tooltip", () => {
+    mockUseUser.mockReturnValue({
+      email: "signed-in@example.com",
+    });
+
+    render(<SubCalendarList />);
+
+    expect(screen.getByText("signed-in@example.com")).toBeInTheDocument();
+    expect(
+      screen.queryByRole("button", { name: /temporary account info/i }),
+    ).not.toBeInTheDocument();
+    expect(
+      screen.queryByText("Sign up to save your changes"),
+    ).not.toBeInTheDocument();
+    expect(screen.getByText("primary")).toBeInTheDocument();
+  });
+
+  it("renders temporary account with a hover tooltip when there is no email", async () => {
+    const user = userEvent.setup();
+
+    mockUseUser.mockReturnValue({
+      email: undefined,
+    });
+
+    render(<SubCalendarList />);
+
+    const infoButton = screen.getByRole("button", {
+      name: /temporary account info/i,
+    });
+
+    expect(screen.getByText("Temporary account")).toBeInTheDocument();
+    expect(screen.queryByText("primary")).not.toBeInTheDocument();
+
+    await user.hover(infoButton);
+
+    await waitFor(() => {
+      expect(
+        screen.getByText("Sign up to save your changes"),
+      ).toBeInTheDocument();
+    });
+  });
+
+  it("opens the sign up auth modal when the temporary account icon is clicked", async () => {
+    const user = userEvent.setup();
+
+    mockUseUser.mockReturnValue({
+      email: undefined,
+    });
+
+    render(<SubCalendarList />);
+
+    await user.click(
+      screen.getByRole("button", {
+        name: /temporary account info/i,
+      }),
+    );
+
+    expect(openModal).toHaveBeenCalledWith("signUp");
+  });
+});
diff --git a/packages/web/src/views/Calendar/components/Sidebar/MonthTab/SubCalendarList/SubCalendarList.tsx b/packages/web/src/views/Calendar/components/Sidebar/MonthTab/SubCalendarList/SubCalendarList.tsx
index 9195a97b8..9ec61403d 100644
--- a/packages/web/src/views/Calendar/components/Sidebar/MonthTab/SubCalendarList/SubCalendarList.tsx
+++ b/packages/web/src/views/Calendar/components/Sidebar/MonthTab/SubCalendarList/SubCalendarList.tsx
@@ -1,39 +1,59 @@
-import React, { type FC } from "react";
-import { theme } from "@web/common/styles/theme";
-import { Divider } from "@web/components/Divider";
-import { Text } from "@web/components/Text";
-import {
-  CalendarLabel,
-  CalendarList,
-  CalendarListContainer,
-} from "../../styled";
+import { type FC, useCallback } from "react";
+import { InfoIcon } from "@phosphor-icons/react";
+import { useUser } from "@web/auth/compass/user/hooks/useUser";
+import { useAuthModal } from "@web/components/AuthModal/hooks/useAuthModal";
+import { TooltipWrapper } from "@web/components/Tooltip/TooltipWrapper";
+
+const TEMPORARY_ACCOUNT_MESSAGE = "Sign up to save your changes";
 
 export const SubCalendarList: FC = () => {
+  const { email } = useUser();
+  const { openModal } = useAuthModal();
+  const isTemporaryAccount = !email;
+  const headingText = email ?? "Temporary account";
+  const handleOpenSignUp = useCallback(() => {
+    openModal("signUp");
+  }, [openModal]);
+
   return (
     <>
-      <Divider
+      <div
+        className="from-fg-primary-dark to-fg-primary h-[2px] w-full bg-linear-to-r"
         role="separator"
         title="right sidebar divider"
-        withAnimation={false}
       />
-      <CalendarListContainer>
-        <Text color={theme.color.text.light} size="xl">
-          Calendars
-        </Text>
-        <CalendarList>
-          <CalendarLabel>
-            <input
-              checked={true}
-              disabled={true}
-              type="checkbox"
-              style={{ marginRight: "6px" }}
-            />
-            <Text color={theme.color.text.light} size="m">
-              primary
-            </Text>
-          </CalendarLabel>
-        </CalendarList>
-      </CalendarListContainer>
+      <div>
+        <div className="mb-1 flex items-center gap-1.5">
+          <span className="text-text-light text">{headingText}</span>
+          {isTemporaryAccount ? (
+            <TooltipWrapper
+              description={TEMPORARY_ACCOUNT_MESSAGE}
+              onClick={handleOpenSignUp}
+            >
+              <button
+                aria-label="Temporary account info"
+                className="text-text-darkPlaceholder inline-flex cursor-pointer items-center p-0"
+                type="button"
+              >
+                <InfoIcon aria-hidden="true" size={14} />
+              </button>
+            </TooltipWrapper>
+          ) : null}
+        </div>
+        {!isTemporaryAccount ? (
+          <ul className="pl-[10px]">
+            <label className="flex items-center">
+              <input
+                checked={true}
+                className="mr-1.5"
+                disabled={true}
+                type="checkbox"
+              />
+              <span className="text-text-light text-base">primary</span>
+            </label>
+          </ul>
+        ) : null}
+      </div>
     </>
   );
 };
diff --git a/packages/web/src/views/Calendar/components/Sidebar/Sidebar.interactions.test.tsx b/packages/web/src/views/Calendar/components/Sidebar/Sidebar.interactions.test.tsx
index af16e35a5..ef2ac69db 100644
--- a/packages/web/src/views/Calendar/components/Sidebar/Sidebar.interactions.test.tsx
+++ b/packages/web/src/views/Calendar/components/Sidebar/Sidebar.interactions.test.tsx
@@ -15,7 +15,7 @@ import { ENV_WEB } from "@web/common/constants/env.constants";
 import { CalendarView } from "@web/views/Calendar";
 import { freshenEventStartEndDate } from "@web/views/Calendar/calendar.render.test.utils";
 
-jest.mock("@web/auth/session/session.util", () => ({
+jest.mock("@web/auth/compass/session/session.util", () => ({
   getUserId: async () => "test-user-id",
 }));
 
diff --git a/packages/web/src/views/Calendar/components/Sidebar/SidebarIconRow/SidebarIconRow.test.tsx b/packages/web/src/views/Calendar/components/Sidebar/SidebarIconRow/SidebarIconRow.test.tsx
index a22eb5e4b..67f00fb98 100644
--- a/packages/web/src/views/Calendar/components/Sidebar/SidebarIconRow/SidebarIconRow.test.tsx
+++ b/packages/web/src/views/Calendar/components/Sidebar/SidebarIconRow/SidebarIconRow.test.tsx
@@ -1,23 +1,8 @@
 import type { ReactNode } from "react";
-import { fireEvent, screen } from "@testing-library/react";
+import { screen } from "@testing-library/react";
 import { render } from "@web/__tests__/utils/render.test.util";
-import { SyncApi } from "@web/common/apis/sync.api";
 import { SidebarIconRow } from "@web/views/Calendar/components/Sidebar/SidebarIconRow";
 
-const mockLogin = jest.fn();
-
-jest.mock("@web/auth/hooks/google/useGoogleAuth/useGoogleAuth", () => ({
-  useGoogleAuth: () => ({
-    login: mockLogin,
-  }),
-}));
-
-jest.mock("@web/common/apis/sync.api", () => ({
-  SyncApi: {
-    importGCal: jest.fn().mockResolvedValue(undefined),
-  },
-}));
-
 jest.mock("@web/common/hooks/useVersionCheck", () => ({
   useVersionCheck: () => ({
     isUpdateAvailable: false,
@@ -48,177 +33,13 @@ jest.mock("@web/components/Tooltip/TooltipWrapper", () => ({
 }));
 
 describe("SidebarIconRow", () => {
-  beforeEach(() => {
-    jest.clearAllMocks();
-  });
-
-  it("shows the connect icon action when Google Calendar is not connected", () => {
-    render(<SidebarIconRow />, {
-      state: {
-        userMetadata: {
-          current: {
-            google: {
-              connectionState: "NOT_CONNECTED",
-            },
-          },
-        },
-      },
-    });
-
-    expect(
-      screen.getByRole("button", {
-        name: "Google Calendar not connected. Click to connect.",
-      }),
-    ).toBeEnabled();
-    expect(
-      screen.getByRole("status", {
-        name: "Google Calendar not connected. Click to connect.",
-      }),
-    ).toBeInTheDocument();
-  });
-
-  it("shows the reconnect icon action when reconnect is required", () => {
-    render(<SidebarIconRow />, {
-      state: {
-        userMetadata: {
-          current: {
-            google: {
-              connectionState: "RECONNECT_REQUIRED",
-            },
-          },
-        },
-      },
-    });
-
-    expect(
-      screen.getByRole("button", {
-        name: "Google Calendar needs reconnecting. Click to reconnect.",
-      }),
-    ).toBeEnabled();
-    expect(
-      screen.getByRole("status", {
-        name: "Google Calendar needs reconnecting. Click to reconnect.",
-      }),
-    ).toBeInTheDocument();
-  });
-
-  it("disables the sidebar action when Google Calendar is healthy", () => {
-    render(<SidebarIconRow />, {
-      state: {
-        userMetadata: {
-          current: {
-            google: {
-              connectionState: "HEALTHY",
-            },
-          },
-        },
-      },
-    });
-
-    expect(
-      screen.getByRole("button", {
-        name: "Google Calendar connected.",
-      }),
-    ).toBeDisabled();
-    expect(
-      screen.getByRole("status", {
-        name: "Google Calendar connected.",
-      }),
-    ).toBeInTheDocument();
-  });
-
-  it("disables the sidebar action while Google Calendar is importing", () => {
-    render(<SidebarIconRow />, {
-      state: {
-        userMetadata: {
-          current: {
-            google: {
-              connectionState: "IMPORTING",
-            },
-          },
-        },
-      },
-    });
-
-    expect(
-      screen.getByRole("button", {
-        name: "Google Calendar is syncing in the background.",
-      }),
-    ).toBeDisabled();
-    expect(
-      screen.getByRole("status", {
-        name: "Google Calendar is syncing in the background.",
-      }),
-    ).toBeInTheDocument();
-  });
-
-  it("shows the background import spinner while Google Calendar is importing", () => {
-    render(<SidebarIconRow />, {
-      state: {
-        sync: {
-          importGCal: {
-            isProcessing: true,
-          },
-        },
-      },
-    });
+  it("does not render the background import spinner in the sidebar", () => {
+    render(<SidebarIconRow />);
 
     expect(
-      screen.getByRole("button", {
-        name: "Importing your calendar events in the background",
-      }),
-    ).toBeInTheDocument();
-  });
-
-  it("clicks through to repair when Google Calendar needs attention", () => {
-    render(<SidebarIconRow />, {
-      state: {
-        userMetadata: {
-          current: {
-            google: {
-              connectionState: "ATTENTION",
-            },
-          },
-        },
-      },
-    });
-
-    fireEvent.click(
-      screen.getByRole("button", {
-        name: "Google Calendar needs repair. Click to repair.",
-      }),
-    );
-
-    expect(SyncApi.importGCal).toHaveBeenCalledWith({ force: true });
-  });
-
-  it("shows a disabled warning spinner while a repair is active", () => {
-    render(<SidebarIconRow />, {
-      state: {
-        userMetadata: {
-          current: {
-            google: {
-              connectionState: "ATTENTION",
-            },
-          },
-        },
-        sync: {
-          importGCal: {
-            isRepairing: true,
-          },
-        },
-      },
-    });
-
-    expect(
-      screen.getByRole("button", {
-        name: "Repairing Google Calendar in the background.",
-      }),
-    ).toBeDisabled();
-    expect(
-      screen.getByRole("status", {
-        name: "Repairing Google Calendar in the background.",
+      screen.queryByRole("button", {
+        name: "Syncing Google Calendar in the background.",
       }),
-    ).toBeInTheDocument();
+    ).not.toBeInTheDocument();
   });
 });
diff --git a/packages/web/src/views/Calendar/components/Sidebar/SidebarIconRow/SidebarIconRow.tsx b/packages/web/src/views/Calendar/components/Sidebar/SidebarIconRow/SidebarIconRow.tsx
index bcf1f1f44..c3fc49de9 100644
--- a/packages/web/src/views/Calendar/components/Sidebar/SidebarIconRow/SidebarIconRow.tsx
+++ b/packages/web/src/views/Calendar/components/Sidebar/SidebarIconRow/SidebarIconRow.tsx
@@ -1,22 +1,12 @@
-import {
-  CloudArrowUpIcon,
-  CloudWarningIcon,
-  LinkBreakIcon,
-  LinkIcon,
-} from "@phosphor-icons/react";
-import { useConnectGoogle } from "@web/auth/hooks/google/useConnectGoogle/useConnectGoogle";
 import { useVersionCheck } from "@web/common/hooks/useVersionCheck";
 import { theme } from "@web/common/styles/theme";
-import { type ConnectionStatusIcon } from "@web/common/types/icon.types";
 import { getModifierKeyIcon } from "@web/common/utils/shortcut/shortcut.util";
 import { CalendarIcon } from "@web/components/Icons/Calendar";
 import { CommandIcon } from "@web/components/Icons/Command";
 import { RefreshIcon } from "@web/components/Icons/Refresh";
-import { SpinnerIcon } from "@web/components/Icons/Spinner";
 import { TodoIcon } from "@web/components/Icons/Todo";
 import { Text } from "@web/components/Text";
 import { TooltipWrapper } from "@web/components/Tooltip/TooltipWrapper";
-import { selectImportGCalState } from "@web/ducks/events/selectors/sync.selector";
 import { selectSidebarTab } from "@web/ducks/events/selectors/view.selectors";
 import { viewSlice } from "@web/ducks/events/slices/view.slice";
 import { selectIsCmdPaletteOpen } from "@web/ducks/settings/selectors/settings.selectors";
@@ -28,75 +18,11 @@ import {
   RightIconGroup,
 } from "@web/views/Calendar/components/Sidebar/styled";
 
-/**
- * Returns the icon for the current Google connection state.
- * Icons are decorative (aria-hidden) since the parent status container
- * provides the accessible name via aria-label.
- */
-const getGoogleStatusIcon = ({
-  icon,
-  tone = "default",
-}: {
-  icon: ConnectionStatusIcon;
-
-  tone?: "default" | "warning";
-}) => {
-  switch (icon) {
-    case "LinkBreakIcon":
-      return (
-        <LinkBreakIcon
-          aria-hidden="true"
-          color={theme.color.status.error}
-          size={24}
-        />
-      );
-    case "LinkIcon":
-      return (
-        <LinkIcon
-          aria-hidden="true"
-          color={theme.color.text.darkPlaceholder}
-          size={24}
-        />
-      );
-    case "SpinnerIcon":
-      return (
-        <SpinnerIcon
-          aria-hidden="true"
-          color={
-            tone === "warning"
-              ? theme.color.status.warning
-              : theme.color.status.info
-          }
-          size={24}
-        />
-      );
-    case "CloudWarningIcon":
-      return (
-        <CloudWarningIcon
-          aria-hidden="true"
-          color={theme.color.status.warning}
-          size={24}
-        />
-      );
-    case "CloudArrowUpIcon":
-      return (
-        <CloudArrowUpIcon
-          aria-hidden="true"
-          color={theme.color.text.darkPlaceholder}
-          size={24}
-        />
-      );
-  }
-};
-
 export const SidebarIconRow = () => {
   const dispatch = useAppDispatch();
   const tab = useAppSelector(selectSidebarTab);
-  const gCalImport = useAppSelector(selectImportGCalState);
   const isCmdPaletteOpen = useAppSelector(selectIsCmdPaletteOpen);
   const { isUpdateAvailable } = useVersionCheck();
-  const { sidebarStatus } = useConnectGoogle();
-  const isBackgroundImporting = gCalImport.isProcessing === true;
 
   const handleUpdateReload = () => {
     window.location.reload();
@@ -164,27 +90,6 @@ export const SidebarIconRow = () => {
             }
           />
         </TooltipWrapper>
-        <div
-          role="status"
-          aria-live="polite"
-          aria-label={sidebarStatus.tooltip}
-        >
-          <TooltipWrapper
-            description={sidebarStatus.tooltip}
-            disabled={sidebarStatus.isDisabled}
-            onClick={sidebarStatus.onSelect}
-          >
-            {getGoogleStatusIcon({
-              icon: sidebarStatus.icon,
-              tone: sidebarStatus.tone,
-            })}
-          </TooltipWrapper>
-        </div>
-        {isBackgroundImporting ? (
-          <TooltipWrapper description="Importing your calendar events in the background">
-            <SpinnerIcon />
-          </TooltipWrapper>
-        ) : undefined}
         {isUpdateAvailable ? (
           <TooltipWrapper
             description="Get latest version"
diff --git a/packages/web/src/views/Calendar/components/Sidebar/styled.ts b/packages/web/src/views/Calendar/components/Sidebar/styled.ts
index 446ebe571..c469bcd5d 100644
--- a/packages/web/src/views/Calendar/components/Sidebar/styled.ts
+++ b/packages/web/src/views/Calendar/components/Sidebar/styled.ts
@@ -9,8 +9,6 @@ import { type SectionProps } from "./sidebar.types";
 
 const ICON_ROW_HEIGHT = 40;
 
-export const CalendarListContainer = styled.div``;
-
 export const CalendarLabel = styled.label`
   align-items: center;
   display: flex;
diff --git a/packages/web/src/views/CmdPalette/CmdPalette.test.tsx b/packages/web/src/views/CmdPalette/CmdPalette.test.tsx
index 88f73078c..4c9e61000 100644
--- a/packages/web/src/views/CmdPalette/CmdPalette.test.tsx
+++ b/packages/web/src/views/CmdPalette/CmdPalette.test.tsx
@@ -58,7 +58,7 @@ jest.mock("@web/common/utils/dom/event-target-visibility.util", () => ({
 }));
 
 const mockLogin = jest.fn();
-jest.mock("@web/auth/hooks/google/useGoogleAuth/useGoogleAuth", () => ({
+jest.mock("@web/auth/google/hooks/useGoogleAuth/useGoogleAuth", () => ({
   useGoogleAuth: () => ({
     login: mockLogin,
   }),
diff --git a/packages/web/src/views/CmdPalette/CmdPalette.tsx b/packages/web/src/views/CmdPalette/CmdPalette.tsx
index 91bd4754b..2753ba6aa 100644
--- a/packages/web/src/views/CmdPalette/CmdPalette.tsx
+++ b/packages/web/src/views/CmdPalette/CmdPalette.tsx
@@ -6,7 +6,7 @@ import {
   SOMEDAY_WEEK_LIMIT_MSG,
 } from "@core/constants/core.constants";
 import { Categories_Event } from "@core/types/event.types";
-import { useConnectGoogle } from "@web/auth/hooks/google/useConnectGoogle/useConnectGoogle";
+import { useConnectGoogle } from "@web/auth/google/hooks/useConnectGoogle/useConnectGoogle";
 import { moreCommandPaletteItems } from "@web/common/constants/more.cmd.constants";
 import { useAuthCmdItems } from "@web/common/hooks/useAuthCmdItems";
 import { pressKey } from "@web/common/utils/dom/event-emitter.util";
diff --git a/packages/web/src/views/Day/components/DayCmdPalette.test.tsx b/packages/web/src/views/Day/components/DayCmdPalette.test.tsx
index 2eacacfac..d560a4c31 100644
--- a/packages/web/src/views/Day/components/DayCmdPalette.test.tsx
+++ b/packages/web/src/views/Day/components/DayCmdPalette.test.tsx
@@ -2,7 +2,7 @@ import { resolveModifier } from "@tanstack/react-hotkeys";
 import { fireEvent, screen } from "@testing-library/react";
 import userEvent from "@testing-library/user-event";
 import { render } from "@web/__tests__/__mocks__/mock.render";
-import * as useGoogleAuthModule from "@web/auth/hooks/google/useGoogleAuth/useGoogleAuth";
+import * as useGoogleAuthModule from "@web/auth/google/hooks/useGoogleAuth/useGoogleAuth";
 import { SyncApi } from "@web/common/apis/sync.api";
 import { ROOT_ROUTES } from "@web/common/constants/routes";
 import * as eventUtil from "@web/common/utils/event/event.util";
@@ -110,18 +110,17 @@ jest.mock("@web/common/utils/dom/event-target-visibility.util", () => ({
 
 // Mock event utility functions
 jest.mock("@web/common/utils/event/event.util");
-
-jest.mock("@web/store/store.hooks", () => ({
-  useAppDispatch: () => mockDispatch,
-  useAppSelector: jest.requireActual("@web/store/store.hooks").useAppSelector,
-}));
-
 jest.mock("@web/common/apis/sync.api", () => ({
   SyncApi: {
     importGCal: jest.fn().mockResolvedValue(undefined),
   },
 }));
 
+jest.mock("@web/store/store.hooks", () => ({
+  useAppDispatch: () => mockDispatch,
+  useAppSelector: jest.requireActual("@web/store/store.hooks").useAppSelector,
+}));
+
 function Component() {
   useGlobalShortcuts();
 
diff --git a/packages/web/src/views/Day/components/DayCmdPalette.tsx b/packages/web/src/views/Day/components/DayCmdPalette.tsx
index aaff4fabe..6477b84da 100644
--- a/packages/web/src/views/Day/components/DayCmdPalette.tsx
+++ b/packages/web/src/views/Day/components/DayCmdPalette.tsx
@@ -2,7 +2,7 @@ import { useState } from "react";
 import CommandPalette, { filterItems, getItemIndex } from "react-cmdk";
 import "react-cmdk/dist/cmdk.css";
 import dayjs from "@core/util/date/dayjs";
-import { useConnectGoogle } from "@web/auth/hooks/google/useConnectGoogle/useConnectGoogle";
+import { useConnectGoogle } from "@web/auth/google/hooks/useConnectGoogle/useConnectGoogle";
 import { moreCommandPaletteItems } from "@web/common/constants/more.cmd.constants";
 import { VIEW_SHORTCUTS } from "@web/common/constants/shortcuts.constants";
 import { useAuthCmdItems } from "@web/common/hooks/useAuthCmdItems";
diff --git a/packages/web/src/views/Day/components/Header/Header.tsx b/packages/web/src/views/Day/components/Header/Header.tsx
index 49428c8c0..c78194851 100644
--- a/packages/web/src/views/Day/components/Header/Header.tsx
+++ b/packages/web/src/views/Day/components/Header/Header.tsx
@@ -1,16 +1,10 @@
 import { type FC, useCallback, useRef } from "react";
 import { theme } from "@web/common/styles/theme";
-import { AccountIcon } from "@web/components/AuthModal/AccountIcon";
-import { AlignItems } from "@web/components/Flex/styled";
+import { HeaderInfoIcon } from "@web/components/HeaderInfoIcon/HeaderInfoIcon";
 import { SidebarIcon } from "@web/components/Icons/Sidebar";
 import { SelectView } from "@web/components/SelectView/SelectView";
 import { TooltipWrapper } from "@web/components/Tooltip/TooltipWrapper";
 import { Reminder } from "@web/views/Calendar/components/Header/Reminder/Reminder";
-import {
-  StyledHeaderRow,
-  StyledLeftGroup,
-  StyledRightGroup,
-} from "@web/views/Calendar/components/Header/styled";
 import { useReminderHotkey } from "@web/views/Calendar/hooks/shortcuts/useFocusHotkey";
 
 interface Props {
@@ -35,7 +29,7 @@ export const Header: FC<Props> = ({
   useReminderHotkey(handleFocusReminder, [handleFocusReminder], showReminder);
 
   return (
-    <StyledHeaderRow alignItems={AlignItems.BASELINE}>
+    <div className="text-text-light relative flex h-20 w-full items-baseline justify-between">
       <TooltipWrapper
         description={isSidebarOpen ? "Hide shortcuts" : "Show shortcuts"}
         onClick={onToggleSidebar}
@@ -49,14 +43,14 @@ export const Header: FC<Props> = ({
           }
         />
       </TooltipWrapper>
-      <StyledLeftGroup />
+      <div className="z-2 flex items-center justify-between" />
 
       {showReminder && <Reminder ref={reminderRef} />}
 
-      <StyledRightGroup>
-        <AccountIcon />
+      <div className="z-2 flex h-full items-center justify-between">
+        <HeaderInfoIcon />
         <SelectView />
-      </StyledRightGroup>
-    </StyledHeaderRow>
+      </div>
+    </div>
   );
 };
diff --git a/packages/web/src/views/Forms/hooks/useOpenEventForm.test.ts b/packages/web/src/views/Forms/hooks/useOpenEventForm.test.ts
index 675eff90c..24dba5793 100644
--- a/packages/web/src/views/Forms/hooks/useOpenEventForm.test.ts
+++ b/packages/web/src/views/Forms/hooks/useOpenEventForm.test.ts
@@ -13,7 +13,7 @@ import { eventsStore, setDraft } from "@web/store/events";
 import { useOpenEventForm } from "@web/views/Forms/hooks/useOpenEventForm";
 
 // Mocks
-jest.mock("@web/auth/session/session.util");
+jest.mock("@web/auth/compass/session/session.util");
 jest.mock("@web/common/context/pointer-position");
 jest.mock("@web/common/utils/dom/event-emitter.util");
 jest.mock("@web/views/Day/hooks/navigation/useDateInView");
@@ -57,7 +57,9 @@ describe("useOpenEventForm", () => {
     (isElementInViewport as jest.Mock).mockReturnValue(true);
   });
 
-  const { getUserId } = jest.requireMock("@web/auth/session/session.util");
+  const { getUserId } = jest.requireMock(
+    "@web/auth/compass/session/session.util",
+  );
 
   const {
     getPointerPosition,
diff --git a/packages/web/src/views/Forms/hooks/useOpenEventForm.ts b/packages/web/src/views/Forms/hooks/useOpenEventForm.ts
index ab6f22f0f..a90589ee2 100644
--- a/packages/web/src/views/Forms/hooks/useOpenEventForm.ts
+++ b/packages/web/src/views/Forms/hooks/useOpenEventForm.ts
@@ -4,7 +4,7 @@ import { getEntity } from "@ngneat/elf-entities";
 import { Origin, Priorities } from "@core/constants/core.constants";
 import { type Schema_Event, type WithCompassId } from "@core/types/event.types";
 import dayjs, { type Dayjs } from "@core/util/date/dayjs";
-import { getUserId } from "@web/auth/session/session.util";
+import { getUserId } from "@web/auth/compass/session/session.util";
 import {
   DATA_EVENT_ELEMENT_ID,
   ID_GRID_EVENTS_TIMED,
diff --git a/packages/web/src/views/Now/components/NowCmdPalette.test.tsx b/packages/web/src/views/Now/components/NowCmdPalette.test.tsx
index f4750f49a..c01adfc88 100644
--- a/packages/web/src/views/Now/components/NowCmdPalette.test.tsx
+++ b/packages/web/src/views/Now/components/NowCmdPalette.test.tsx
@@ -1,6 +1,10 @@
 import type { ReactNode } from "react";
 import { fireEvent, screen, waitFor } from "@testing-library/react";
 import { render } from "@web/__tests__/utils/render.test.util";
+import {
+  resetGoogleSyncUIStateForTests,
+  setRepairingSyncIndicatorOverride,
+} from "@web/auth/google/state/google.sync.state";
 import { SyncApi } from "@web/common/apis/sync.api";
 import * as eventEmitterUtil from "@web/common/utils/dom/event-emitter.util";
 import { NowCmdPalette } from "@web/views/Now/components/NowCmdPalette";
@@ -104,7 +108,7 @@ jest.mock("@web/common/utils/dom/event-target-visibility.util", () => ({
 
 // Mock useGoogleAuth
 const mockLogin = jest.fn();
-jest.mock("@web/auth/hooks/google/useGoogleAuth/useGoogleAuth", () => ({
+jest.mock("@web/auth/google/hooks/useGoogleAuth/useGoogleAuth", () => ({
   useGoogleAuth: () => ({
     login: mockLogin,
   }),
@@ -125,6 +129,7 @@ describe("NowCmdPalette", () => {
 
   beforeEach(() => {
     jest.clearAllMocks();
+    resetGoogleSyncUIStateForTests();
   });
 
   it("should render when open", () => {
@@ -260,6 +265,8 @@ describe("NowCmdPalette", () => {
     });
 
     it("shows a disabled repairing action while a repair is active", () => {
+      setRepairingSyncIndicatorOverride();
+
       render(<NowCmdPalette />, {
         state: {
           ...initialState,
@@ -270,11 +277,6 @@ describe("NowCmdPalette", () => {
               },
             },
           },
-          sync: {
-            importGCal: {
-              isRepairing: true,
-            },
-          },
         },
       });
 
diff --git a/packages/web/src/views/Now/components/NowCmdPalette.tsx b/packages/web/src/views/Now/components/NowCmdPalette.tsx
index 77380cb4e..f05ce96ca 100644
--- a/packages/web/src/views/Now/components/NowCmdPalette.tsx
+++ b/packages/web/src/views/Now/components/NowCmdPalette.tsx
@@ -1,7 +1,7 @@
 import { useState } from "react";
 import CommandPalette, { filterItems, getItemIndex } from "react-cmdk";
 import "react-cmdk/dist/cmdk.css";
-import { useConnectGoogle } from "@web/auth/hooks/google/useConnectGoogle/useConnectGoogle";
+import { useConnectGoogle } from "@web/auth/google/hooks/useConnectGoogle/useConnectGoogle";
 import { moreCommandPaletteItems } from "@web/common/constants/more.cmd.constants";
 import { VIEW_SHORTCUTS } from "@web/common/constants/shortcuts.constants";
 import { useAuthCmdItems } from "@web/common/hooks/useAuthCmdItems";
diff --git a/packages/web/src/views/Root.tsx b/packages/web/src/views/Root.tsx
index b7e59fffe..d92b7be56 100644
--- a/packages/web/src/views/Root.tsx
+++ b/packages/web/src/views/Root.tsx
@@ -1,4 +1,4 @@
-import { UserProvider } from "@web/auth/context/UserProvider";
+import { UserProvider } from "@web/auth/compass/user/context/UserProvider";
 import { useIsMobile } from "@web/common/hooks/useIsMobile";
 import { AuthenticatedLayout } from "@web/components/AuthenticatedLayout/AuthenticatedLayout";
 import { GlobalShortcutsHost } from "@web/components/CompassProvider/CompassProvider";