diff --git a/apps/desktop/src/electron/ElectronMenu.test.ts b/apps/desktop/src/electron/ElectronMenu.test.ts
index 4dd8066e3c6..3dc218d8252 100644
--- a/apps/desktop/src/electron/ElectronMenu.test.ts
+++ b/apps/desktop/src/electron/ElectronMenu.test.ts
@@ -1,5 +1,8 @@
 import { assert, describe, it } from "@effect/vitest";
+import { HostProcessPlatform } from "@t3tools/shared/hostProcess";
+import * as Cause from "effect/Cause";
 import * as Effect from "effect/Effect";
+import * as Layer from "effect/Layer";
 import * as Option from "effect/Option";
 import type * as Electron from "electron";
 import { beforeEach, vi } from "vite-plus/test";
@@ -24,6 +27,10 @@ vi.mock("electron", () => ({
 
 import * as ElectronMenu from "./ElectronMenu.ts";
 
+const TestLayer = ElectronMenu.layer.pipe(
+  Layer.provide(Layer.succeed(HostProcessPlatform, "linux")),
+);
+
 describe("ElectronMenu", () => {
   beforeEach(() => {
     buildFromTemplateMock.mockReset();
@@ -42,7 +49,7 @@ describe("ElectronMenu", () => {
 
       assert.isTrue(Option.isNone(selectedItemId));
       assert.equal(buildFromTemplateMock.mock.calls.length, 0);
-    }).pipe(Effect.provide(ElectronMenu.layer)),
+    }).pipe(Effect.provide(TestLayer)),
   );
 
   it.effect("resolves with the clicked leaf item id", () =>
@@ -69,7 +76,7 @@ describe("ElectronMenu", () => {
       });
 
       assert.equal(Option.getOrNull(selectedItemId), "copy");
-    }).pipe(Effect.provide(ElectronMenu.layer)),
+    }).pipe(Effect.provide(TestLayer)),
   );
 
   it.effect("resolves with none when the menu closes without a click", () =>
@@ -93,7 +100,7 @@ describe("ElectronMenu", () => {
         enabled: true,
         click: buildFromTemplateMock.mock.calls[0]?.[0][0].click,
       });
-    }).pipe(Effect.provide(ElectronMenu.layer)),
+    }).pipe(Effect.provide(TestLayer)),
   );
 
   it.effect("defers popupTemplate side effects until the returned Effect runs", () =>
@@ -114,6 +121,89 @@ describe("ElectronMenu", () => {
 
       assert.equal(buildFromTemplateMock.mock.calls.length, 1);
       assert.equal(popupMock.mock.calls.length, 1);
-    }).pipe(Effect.provide(ElectronMenu.layer)),
+    }).pipe(Effect.provide(TestLayer)),
+  );
+
+  it.effect("preserves application-menu failures as structured defects", () =>
+    Effect.gen(function* () {
+      const cause = new Error("application menu build failed");
+      buildFromTemplateMock.mockImplementationOnce(() => {
+        throw cause;
+      });
+
+      const electronMenu = yield* ElectronMenu.ElectronMenu;
+      const exit = yield* Effect.exit(
+        electronMenu.setApplicationMenu([{ label: "File" }, { label: "Edit" }]),
+      );
+
+      assert.equal(exit._tag, "Failure");
+      if (exit._tag === "Failure") {
+        const error = Cause.squash(exit.cause);
+        assert.instanceOf(error, ElectronMenu.ElectronMenuOperationError);
+        assert.equal(error.operation, "set-application-menu");
+        assert.equal(error.platform, "linux");
+        assert.isNull(error.windowId);
+        assert.equal(error.itemCount, 2);
+        assert.strictEqual(error.cause, cause);
+        assert.notInclude(error.message, cause.message);
+      }
+    }).pipe(Effect.provide(TestLayer)),
+  );
+
+  it.effect("preserves popup-template failures with window context", () =>
+    Effect.gen(function* () {
+      const cause = new Error("popup failed");
+      buildFromTemplateMock.mockReturnValueOnce({
+        popup: () => {
+          throw cause;
+        },
+      });
+
+      const electronMenu = yield* ElectronMenu.ElectronMenu;
+      const exit = yield* Effect.exit(
+        electronMenu.popupTemplate({
+          window: { id: 41 } as Electron.BrowserWindow,
+          template: [{ label: "Copy" }],
+        }),
+      );
+
+      assert.equal(exit._tag, "Failure");
+      if (exit._tag === "Failure") {
+        const error = Cause.squash(exit.cause);
+        assert.instanceOf(error, ElectronMenu.ElectronMenuOperationError);
+        assert.equal(error.operation, "popup-template");
+        assert.equal(error.windowId, 41);
+        assert.equal(error.itemCount, 1);
+        assert.strictEqual(error.cause, cause);
+      }
+    }).pipe(Effect.provide(TestLayer)),
+  );
+
+  it.effect("preserves context-menu failures with normalized item context", () =>
+    Effect.gen(function* () {
+      const cause = new Error("context menu build failed");
+      buildFromTemplateMock.mockImplementationOnce(() => {
+        throw cause;
+      });
+
+      const electronMenu = yield* ElectronMenu.ElectronMenu;
+      const exit = yield* Effect.exit(
+        electronMenu.showContextMenu({
+          window: { id: 42 } as Electron.BrowserWindow,
+          items: [{ id: "copy", label: "Copy" }],
+          position: Option.none(),
+        }),
+      );
+
+      assert.equal(exit._tag, "Failure");
+      if (exit._tag === "Failure") {
+        const error = Cause.squash(exit.cause);
+        assert.instanceOf(error, ElectronMenu.ElectronMenuOperationError);
+        assert.equal(error.operation, "show-context-menu");
+        assert.equal(error.windowId, 42);
+        assert.equal(error.itemCount, 1);
+        assert.strictEqual(error.cause, cause);
+      }
+    }).pipe(Effect.provide(TestLayer)),
   );
 });
diff --git a/apps/desktop/src/electron/ElectronMenu.ts b/apps/desktop/src/electron/ElectronMenu.ts
index d9eb3b22eff..09fb5d1807d 100644
--- a/apps/desktop/src/electron/ElectronMenu.ts
+++ b/apps/desktop/src/electron/ElectronMenu.ts
@@ -4,6 +4,7 @@ import * as Context from "effect/Context";
 import * as Effect from "effect/Effect";
 import * as Layer from "effect/Layer";
 import * as Option from "effect/Option";
+import * as Schema from "effect/Schema";
 
 import * as Electron from "electron";
 
@@ -23,6 +24,28 @@ export interface ElectronMenuTemplateInput {
   readonly template: readonly Electron.MenuItemConstructorOptions[];
 }
 
+const ElectronMenuOperation = Schema.Literals([
+  "set-application-menu",
+  "popup-template",
+  "show-context-menu",
+]);
+
+export class ElectronMenuOperationError extends Schema.TaggedErrorClass<ElectronMenuOperationError>()(
+  "ElectronMenuOperationError",
+  {
+    operation: ElectronMenuOperation,
+    platform: Schema.String,
+    windowId: Schema.NullOr(Schema.Number),
+    itemCount: Schema.Number,
+    cause: Schema.Defect(),
+  },
+) {
+  override get message(): string {
+    const window = this.windowId === null ? "" : ` for window ${this.windowId}`;
+    return `Electron menu operation ${JSON.stringify(this.operation)} failed${window} with ${this.itemCount} items on ${this.platform}.`;
+  }
+}
+
 export class ElectronMenu extends Context.Service<
   ElectronMenu,
   {
@@ -142,16 +165,36 @@ export const make = Effect.gen(function* () {
 
   return ElectronMenu.of({
     setApplicationMenu: (template) =>
-      Effect.sync(() => {
-        Electron.Menu.setApplicationMenu(Electron.Menu.buildFromTemplate([...template]));
-      }),
+      Effect.try({
+        try: () => {
+          Electron.Menu.setApplicationMenu(Electron.Menu.buildFromTemplate([...template]));
+        },
+        catch: (cause) =>
+          new ElectronMenuOperationError({
+            operation: "set-application-menu",
+            platform,
+            windowId: null,
+            itemCount: template.length,
+            cause,
+          }),
+      }).pipe(Effect.orDie),
     popupTemplate: (input) =>
-      Effect.sync(() => {
-        if (input.template.length === 0) {
-          return;
-        }
-        Electron.Menu.buildFromTemplate([...input.template]).popup({ window: input.window });
-      }),
+      input.template.length === 0
+        ? Effect.void
+        : Effect.try({
+            try: () =>
+              Electron.Menu.buildFromTemplate([...input.template]).popup({
+                window: input.window,
+              }),
+            catch: (cause) =>
+              new ElectronMenuOperationError({
+                operation: "popup-template",
+                platform,
+                windowId: input.window.id,
+                itemCount: input.template.length,
+                cause,
+              }),
+          }).pipe(Effect.orDie),
     showContextMenu: (input) =>
       Effect.callback<Option.Option<string>>((resume) => {
         const normalizedItems = normalizeContextMenuItems(input.items);
@@ -169,21 +212,39 @@ export const make = Effect.gen(function* () {
           resume(Effect.succeed(selectedItemId));
         };
 
-        const menu = Electron.Menu.buildFromTemplate(buildTemplate(normalizedItems, complete));
-        const popupPosition = normalizePosition(input.position);
-        const popupOptions = Option.match(popupPosition, {
-          onNone: (): Electron.PopupOptions => ({
-            window: input.window,
-            callback: () => complete(Option.none()),
-          }),
-          onSome: (position): Electron.PopupOptions => ({
-            window: input.window,
-            x: position.x,
-            y: position.y,
-            callback: () => complete(Option.none()),
-          }),
-        });
-        menu.popup(popupOptions);
+        try {
+          const menu = Electron.Menu.buildFromTemplate(buildTemplate(normalizedItems, complete));
+          const popupPosition = normalizePosition(input.position);
+          const popupOptions = Option.match(popupPosition, {
+            onNone: (): Electron.PopupOptions => ({
+              window: input.window,
+              callback: () => complete(Option.none()),
+            }),
+            onSome: (position): Electron.PopupOptions => ({
+              window: input.window,
+              x: position.x,
+              y: position.y,
+              callback: () => complete(Option.none()),
+            }),
+          });
+          menu.popup(popupOptions);
+        } catch (cause) {
+          if (completed) {
+            return;
+          }
+          completed = true;
+          resume(
+            Effect.die(
+              new ElectronMenuOperationError({
+                operation: "show-context-menu",
+                platform,
+                windowId: input.window.id,
+                itemCount: normalizedItems.length,
+                cause,
+              }),
+            ),
+          );
+        }
       }),
   });
 });