diff --git a/apps/desktop/src/app/DesktopEnvironment.ts b/apps/desktop/src/app/DesktopEnvironment.ts
index 2c5db8a16d8..5a47a8ca8b8 100644
--- a/apps/desktop/src/app/DesktopEnvironment.ts
+++ b/apps/desktop/src/app/DesktopEnvironment.ts
@@ -4,6 +4,7 @@ import type {
   DesktopRuntimeArch,
   DesktopRuntimeInfo,
 } from "@t3tools/contracts";
+import * as NodePath from "@effect/platform-node/NodePath";
 import * as Config from "effect/Config";
 import * as Context from "effect/Context";
 import * as Effect from "effect/Effect";
@@ -246,4 +247,6 @@ const makeDesktopEnvironment = Effect.fn("desktop.environment.make")(function* (
 });
 
 export const layer = (input: MakeDesktopEnvironmentInput) =>
-  Layer.effect(DesktopEnvironment, makeDesktopEnvironment(input));
+  Layer.effect(DesktopEnvironment, makeDesktopEnvironment(input)).pipe(
+    Layer.provide(input.platform === "win32" ? NodePath.layerWin32 : NodePath.layerPosix),
+  );
diff --git a/apps/desktop/src/settings/DesktopClientSettings.test.ts b/apps/desktop/src/settings/DesktopClientSettings.test.ts
index f666e692860..75fb1a20966 100644
--- a/apps/desktop/src/settings/DesktopClientSettings.test.ts
+++ b/apps/desktop/src/settings/DesktopClientSettings.test.ts
@@ -15,6 +15,7 @@ const clientSettings: ClientSettings = {
   autoOpenPlanSidebar: false,
   confirmThreadArchive: true,
   confirmThreadDelete: false,
+  contextMenuStyle: "default",
   dismissedProviderUpdateNotificationKeys: [],
   diffIgnoreWhitespace: true,
   diffWordWrap: true,
diff --git a/apps/web/src/components/settings/SettingsPanels.tsx b/apps/web/src/components/settings/SettingsPanels.tsx
index 76d5d34c355..bb0256e2983 100644
--- a/apps/web/src/components/settings/SettingsPanels.tsx
+++ b/apps/web/src/components/settings/SettingsPanels.tsx
@@ -4,6 +4,7 @@ import { Link } from "@tanstack/react-router";
 import { useCallback, useMemo, useRef, useState } from "react";
 import {
   defaultInstanceIdForDriver,
+  type ContextMenuStyle,
   type DesktopUpdateChannel,
   PROVIDER_DISPLAY_NAMES,
   ProviderDriverKind,
@@ -101,6 +102,12 @@ const TIMESTAMP_FORMAT_LABELS = {
   "24-hour": "24-hour",
 } as const;
 
+const CONTEXT_MENU_STYLE_LABELS = {
+  default: "Default",
+  native: "Native",
+  custom: "Custom",
+} as const satisfies Record<ContextMenuStyle, string>;
+
 const DEFAULT_DRIVER_KIND = ProviderDriverKind.make("codex");
 
 function withoutProviderInstanceKey<V>(
@@ -395,6 +402,9 @@ export function useSettingsRestore(onRestored?: () => void) {
       ...(settings.timestampFormat !== DEFAULT_UNIFIED_SETTINGS.timestampFormat
         ? ["Time format"]
         : []),
+      ...(settings.contextMenuStyle !== DEFAULT_UNIFIED_SETTINGS.contextMenuStyle
+        ? ["Context menu style"]
+        : []),
       ...(settings.sidebarThreadPreviewCount !== DEFAULT_UNIFIED_SETTINGS.sidebarThreadPreviewCount
         ? ["Visible threads"]
         : []),
@@ -434,6 +444,7 @@ export function useSettingsRestore(onRestored?: () => void) {
       settings.confirmThreadArchive,
       settings.confirmThreadDelete,
       settings.addProjectBaseDirectory,
+      settings.contextMenuStyle,
       settings.defaultThreadEnvMode,
       settings.diffIgnoreWhitespace,
       settings.diffWordWrap,
@@ -458,6 +469,7 @@ export function useSettingsRestore(onRestored?: () => void) {
     setTheme("system");
     updateSettings({
       timestampFormat: DEFAULT_UNIFIED_SETTINGS.timestampFormat,
+      contextMenuStyle: DEFAULT_UNIFIED_SETTINGS.contextMenuStyle,
       diffWordWrap: DEFAULT_UNIFIED_SETTINGS.diffWordWrap,
       diffIgnoreWhitespace: DEFAULT_UNIFIED_SETTINGS.diffIgnoreWhitespace,
       sidebarThreadPreviewCount: DEFAULT_UNIFIED_SETTINGS.sidebarThreadPreviewCount,
@@ -594,6 +606,48 @@ export function GeneralSettingsPanel() {
           }
         />
 
+        <SettingsRow
+          title="Context menus"
+          description="Default uses native desktop menus on macOS and custom menus elsewhere."
+          resetAction={
+            settings.contextMenuStyle !== DEFAULT_UNIFIED_SETTINGS.contextMenuStyle ? (
+              <SettingResetButton
+                label="context menu style"
+                onClick={() =>
+                  updateSettings({
+                    contextMenuStyle: DEFAULT_UNIFIED_SETTINGS.contextMenuStyle,
+                  })
+                }
+              />
+            ) : null
+          }
+          control={
+            <Select
+              value={settings.contextMenuStyle}
+              onValueChange={(value) => {
+                if (value === "default" || value === "native" || value === "custom") {
+                  updateSettings({ contextMenuStyle: value });
+                }
+              }}
+            >
+              <SelectTrigger className="w-full sm:w-40" aria-label="Context menu style">
+                <SelectValue>{CONTEXT_MENU_STYLE_LABELS[settings.contextMenuStyle]}</SelectValue>
+              </SelectTrigger>
+              <SelectPopup align="end" alignItemWithTrigger={false}>
+                <SelectItem hideIndicator value="default">
+                  {CONTEXT_MENU_STYLE_LABELS.default}
+                </SelectItem>
+                <SelectItem hideIndicator value="native">
+                  {CONTEXT_MENU_STYLE_LABELS.native}
+                </SelectItem>
+                <SelectItem hideIndicator value="custom">
+                  {CONTEXT_MENU_STYLE_LABELS.custom}
+                </SelectItem>
+              </SelectPopup>
+            </Select>
+          }
+        />
+
         <SettingsRow
           title="Diff line wrapping"
           description="Set the default wrap state when the diff panel opens."
diff --git a/apps/web/src/localApi.test.ts b/apps/web/src/localApi.test.ts
index bc912231d7f..fb247e2a84c 100644
--- a/apps/web/src/localApi.test.ts
+++ b/apps/web/src/localApi.test.ts
@@ -1,5 +1,6 @@
 import {
   CommandId,
+  DEFAULT_CLIENT_SETTINGS,
   DEFAULT_SERVER_SETTINGS,
   type DesktopBridge,
   EnvironmentId,
@@ -591,9 +592,15 @@ describe("wsApi", () => {
     });
   });
 
-  it("forwards context menu metadata to the desktop bridge", async () => {
+  it("forwards context menu metadata to the desktop bridge for native menus", async () => {
     const showContextMenu = vi.fn().mockResolvedValue("delete");
-    getWindowForTest().desktopBridge = makeDesktopBridge({ showContextMenu });
+    getWindowForTest().desktopBridge = makeDesktopBridge({
+      getClientSettings: async () => ({
+        ...DEFAULT_CLIENT_SETTINGS,
+        contextMenuStyle: "native",
+      }),
+      showContextMenu,
+    });
 
     const { createLocalApi } = await import("./localApi");
     const api = createLocalApi(rpcClientMock as never);
@@ -632,6 +639,7 @@ describe("wsApi", () => {
       autoOpenPlanSidebar: false,
       confirmThreadArchive: true,
       confirmThreadDelete: false,
+      contextMenuStyle: "default" as const,
       dismissedProviderUpdateNotificationKeys: [],
       diffIgnoreWhitespace: true,
       diffWordWrap: true,
@@ -695,6 +703,7 @@ describe("wsApi", () => {
       autoOpenPlanSidebar: false,
       confirmThreadArchive: true,
       confirmThreadDelete: false,
+      contextMenuStyle: "default" as const,
       dismissedProviderUpdateNotificationKeys: [],
       diffIgnoreWhitespace: true,
       diffWordWrap: true,
diff --git a/apps/web/src/localApi.ts b/apps/web/src/localApi.ts
index c5ee3f277ca..81961641670 100644
--- a/apps/web/src/localApi.ts
+++ b/apps/web/src/localApi.ts
@@ -1,4 +1,9 @@
-import type { ContextMenuItem, LocalApi } from "@t3tools/contracts";
+import {
+  DEFAULT_CLIENT_SETTINGS,
+  type ContextMenuItem,
+  type ContextMenuStyle,
+  type LocalApi,
+} from "@t3tools/contracts";
 import type { WsRpcClient } from "@t3tools/client-runtime";
 
 import { resetVcsStatusStateForTests } from "./lib/vcsStatusState";
@@ -25,6 +30,7 @@ import {
   writeBrowserSavedEnvironmentRegistry,
   writeBrowserSavedEnvironmentSecret,
 } from "./clientPersistenceStorage";
+import { isMacPlatform } from "./lib/utils";
 
 let cachedApi: LocalApi | undefined;
 
@@ -32,6 +38,28 @@ function unavailableLocalBackendError(): Error {
   return new Error("Local backend API is unavailable before a backend is paired.");
 }
 
+async function readContextMenuStyle(): Promise<ContextMenuStyle> {
+  try {
+    const settings = window.desktopBridge
+      ? await window.desktopBridge.getClientSettings()
+      : readBrowserClientSettings();
+    return settings?.contextMenuStyle ?? DEFAULT_CLIENT_SETTINGS.contextMenuStyle;
+  } catch {
+    return DEFAULT_CLIENT_SETTINGS.contextMenuStyle;
+  }
+}
+
+function shouldUseNativeContextMenu(style: ContextMenuStyle): boolean {
+  if (style === "custom") {
+    return false;
+  }
+  if (style === "native") {
+    return true;
+  }
+  const platform = typeof navigator === "undefined" ? "" : navigator.platform;
+  return Boolean(window.desktopBridge) && isMacPlatform(platform);
+}
+
 function createBrowserLocalApi(rpcClient?: WsRpcClient): LocalApi {
   return {
     dialogs: {
@@ -68,8 +96,13 @@ function createBrowserLocalApi(rpcClient?: WsRpcClient): LocalApi {
         items: readonly ContextMenuItem<T>[],
         position?: { x: number; y: number },
       ): Promise<T | null> => {
-        if (window.desktopBridge) {
-          return window.desktopBridge.showContextMenu(items, position) as Promise<T | null>;
+        const style = await readContextMenuStyle();
+        if (shouldUseNativeContextMenu(style) && window.desktopBridge) {
+          try {
+            return (await window.desktopBridge.showContextMenu(items, position)) as T | null;
+          } catch {
+            return null;
+          }
         }
         return showContextMenuFallback(items, position);
       },
diff --git a/packages/contracts/src/settings.ts b/packages/contracts/src/settings.ts
index 2d115eed98e..e8db543def1 100644
--- a/packages/contracts/src/settings.ts
+++ b/packages/contracts/src/settings.ts
@@ -13,6 +13,10 @@ export const TimestampFormat = Schema.Literals(["locale", "12-hour", "24-hour"])
 export type TimestampFormat = typeof TimestampFormat.Type;
 export const DEFAULT_TIMESTAMP_FORMAT: TimestampFormat = "locale";
 
+export const ContextMenuStyle = Schema.Literals(["default", "native", "custom"]);
+export type ContextMenuStyle = typeof ContextMenuStyle.Type;
+export const DEFAULT_CONTEXT_MENU_STYLE: ContextMenuStyle = "default";
+
 export const SidebarProjectSortOrder = Schema.Literals(["updated_at", "created_at", "manual"]);
 export type SidebarProjectSortOrder = typeof SidebarProjectSortOrder.Type;
 export const DEFAULT_SIDEBAR_PROJECT_SORT_ORDER: SidebarProjectSortOrder = "updated_at";
@@ -43,6 +47,9 @@ export const ClientSettingsSchema = Schema.Struct({
   autoOpenPlanSidebar: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(true))),
   confirmThreadArchive: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(false))),
   confirmThreadDelete: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(true))),
+  contextMenuStyle: ContextMenuStyle.pipe(
+    Schema.withDecodingDefault(Effect.succeed(DEFAULT_CONTEXT_MENU_STYLE)),
+  ),
   dismissedProviderUpdateNotificationKeys: Schema.Array(TrimmedNonEmptyString).pipe(
     Schema.withDecodingDefault(Effect.succeed([])),
   ),
@@ -478,6 +485,7 @@ export const ClientSettingsPatch = Schema.Struct({
   autoOpenPlanSidebar: Schema.optionalKey(Schema.Boolean),
   confirmThreadArchive: Schema.optionalKey(Schema.Boolean),
   confirmThreadDelete: Schema.optionalKey(Schema.Boolean),
+  contextMenuStyle: Schema.optionalKey(ContextMenuStyle),
   diffIgnoreWhitespace: Schema.optionalKey(Schema.Boolean),
   diffWordWrap: Schema.optionalKey(Schema.Boolean),
   favorites: Schema.optionalKey(