diff --git a/apps/roam/src/index.ts b/apps/roam/src/index.ts
index 84a2050e9..8e7a94389 100644
--- a/apps/roam/src/index.ts
+++ b/apps/roam/src/index.ts
@@ -1,4 +1,4 @@
-import { addStyle } from "roamjs-components/dom";
+import { addStyle, getRoamUrl } from "roamjs-components/dom";
 import { render as renderToast } from "roamjs-components/components/Toast";
 import getCurrentUserUid from "roamjs-components/queries/getCurrentUserUid";
 import { runExtension } from "roamjs-components/util";
@@ -32,6 +32,7 @@ import {
   setSyncActivity,
 } from "./utils/syncDgNodesToSupabase";
 import { initPluginTimer } from "./utils/pluginTimer";
+import { createClient } from "@repo/database/lib/client";
 
 const initPostHog = () => {
   posthog.init("phc_SNMmBqwNfcEpNduQ41dBUjtGNEUEKAy6jTn63Fzsrax", {
@@ -126,7 +127,18 @@ export default runExtension(async (onloadArgs) => {
   document.addEventListener("input", discourseNodeSearchTriggerListener);
   document.addEventListener("selectionchange", nodeCreationPopoverListener);
 
-  await initializeSupabaseSync();
+  const supabase = createClient();
+  if (supabase) {
+    const { data } = await supabase
+      .from("Space")
+      .select("url")
+      .eq("url", getRoamUrl())
+      .maybeSingle();
+
+    if (data) {
+      initializeSupabaseSync();
+    }
+  }
 
   const { extensionAPI } = onloadArgs;
   window.roamjs.extension.queryBuilder = {
diff --git a/apps/roam/src/utils/syncDgNodesToSupabase.ts b/apps/roam/src/utils/syncDgNodesToSupabase.ts
index 2eda5bb71..e155f25bd 100644
--- a/apps/roam/src/utils/syncDgNodesToSupabase.ts
+++ b/apps/roam/src/utils/syncDgNodesToSupabase.ts
@@ -18,10 +18,10 @@ import {
 } from "./conceptConversion";
 import { fetchEmbeddingsForNodes } from "./upsertNodesAsContentWithEmbeddings";
 import { convertRoamNodeToLocalContent } from "./upsertNodesAsContentWithEmbeddings";
-import { render as renderToast } from "roamjs-components/components/Toast";
 import { createClient, type DGSupabaseClient } from "@repo/database/lib/client";
 import type { Json, CompositeTypes, Enums } from "@repo/database/dbTypes";
-
+import { render as renderToast } from "roamjs-components/components/Toast";
+import sendErrorEmail from "~/utils/sendErrorEmail";
 type LocalContentDataInput = Partial<CompositeTypes<"content_local_input">>;
 type AccountLocalInput = CompositeTypes<"account_local_input">;
 
@@ -42,6 +42,31 @@ type SyncTaskInfo = {
   shouldProceed: boolean;
 };
 
+const notifyEndSyncFailure = ({
+  status,
+  showToast,
+  reason,
+}: {
+  status: Enums<"task_status">;
+  showToast: boolean;
+  reason: string;
+}): void => {
+  if (showToast) {
+    renderToast({
+      id: "discourse-embedding-error",
+      content: "Failed to complete discourse node embeddings sync",
+      intent: "danger",
+      timeout: 5000,
+    });
+  }
+
+  sendErrorEmail({
+    error: new Error(reason),
+    type: "Sync Failed",
+    context: { status },
+  }).catch(() => {});
+};
+
 export const endSyncTask = async (
   worker: string,
   status: Enums<"task_status">,
@@ -63,23 +88,15 @@ export const endSyncTask = async (
     });
     if (error) {
       console.error("endSyncTask: Error calling end_sync_task:", error);
-      if (showToast)
-        renderToast({
-          id: "discourse-embedding-error",
-          content: "Failed to complete discourse node embeddings sync",
-          intent: "danger",
-          timeout: 5000,
-        });
+      notifyEndSyncFailure({
+        status,
+        showToast,
+        reason: `Supabase end_sync_task RPC failed: ${error.message ?? "Unknown error"}`,
+      });
+
       return;
     } else if (showToast) {
-      if (status === "complete") {
-        renderToast({
-          id: "discourse-embedding-complete",
-          content: "Successfully completed discourse node embeddings sync",
-          intent: "success",
-          timeout: 4000,
-        });
-      } else if (status === "failed") {
+      if (status === "failed") {
         renderToast({
           id: "discourse-embedding-failed",
           content: "Discourse node embeddings sync failed",
@@ -90,13 +107,14 @@ export const endSyncTask = async (
     }
   } catch (error) {
     console.error("endSyncTask: Error calling end_sync_task:", error);
-    if (showToast)
-      renderToast({
-        id: "discourse-embedding-error",
-        content: "Failed to complete discourse node embeddings sync",
-        intent: "danger",
-        timeout: 5000,
-      });
+    notifyEndSyncFailure({
+      status,
+      showToast,
+      reason:
+        error instanceof Error
+          ? `Unexpected error ending sync task: ${error.message}`
+          : "Unexpected non-error thrown while ending sync task",
+    });
   }
 };
 
@@ -468,13 +486,13 @@ export const createOrUpdateDiscourseEmbedding = async (showToast = false) => {
   }
 };
 
-export const initializeSupabaseSync = async () => {
-  const supabase = createClient();
-  if (supabase === null) {
-    doSync = false;
-  } else {
-    doSync = true;
-    // eslint-disable-next-line @typescript-eslint/no-misused-promises
-    activeTimeout = setTimeout(createOrUpdateDiscourseEmbedding, 100, true);
+export const initializeSupabaseSync = (): void => {
+  if (activeTimeout !== null) {
+    clearTimeout(activeTimeout);
+    activeTimeout = null;
   }
+
+  doSync = true;
+  // eslint-disable-next-line @typescript-eslint/no-misused-promises
+  activeTimeout = setTimeout(createOrUpdateDiscourseEmbedding, 100, true);
 };