diff --git a/apps/desktop/src/electron/ElectronDialog.test.ts b/apps/desktop/src/electron/ElectronDialog.test.ts
index 9be62e740b2..388b3fd2c15 100644
--- a/apps/desktop/src/electron/ElectronDialog.test.ts
+++ b/apps/desktop/src/electron/ElectronDialog.test.ts
@@ -1,4 +1,5 @@
 import { assert, describe, it } from "@effect/vitest";
+import * as Cause from "effect/Cause";
 import * as Effect from "effect/Effect";
 import * as Option from "effect/Option";
 import type { BrowserWindow } from "electron";
@@ -90,4 +91,116 @@ describe("ElectronDialog", () => {
       ]);
     }).pipe(Effect.provide(ElectronDialog.layer)),
   );
+
+  it.effect("preserves folder picker request context and cause", () =>
+    Effect.gen(function* () {
+      const cause = new Error("folder picker failed");
+      const owner = { id: 7 } as BrowserWindow;
+      showOpenDialogMock.mockRejectedValue(cause);
+      const dialog = yield* ElectronDialog.ElectronDialog;
+
+      const error = yield* Effect.flip(
+        dialog.pickFolder({
+          owner: Option.some(owner),
+          defaultPath: Option.some("/workspace"),
+        }),
+      );
+
+      assert.instanceOf(error, ElectronDialog.ElectronDialogPickFolderError);
+      assert.isTrue(ElectronDialog.isElectronDialogError(error));
+      assert.strictEqual(error.ownerWindowId, 7);
+      assert.strictEqual(error.defaultPath, "/workspace");
+      assert.strictEqual(error.cause, cause);
+      assert.include(error.message, "window 7");
+      assert.include(error.message, "/workspace");
+      assert.notInclude(error.message, cause.message);
+    }).pipe(Effect.provide(ElectronDialog.layer)),
+  );
+
+  it.effect("preserves confirmation request context and cause", () =>
+    Effect.gen(function* () {
+      const cause = new Error("confirmation failed");
+      const owner = { id: 9 } as BrowserWindow;
+      showMessageBoxMock.mockRejectedValue(cause);
+      const dialog = yield* ElectronDialog.ElectronDialog;
+
+      const error = yield* Effect.flip(
+        dialog.confirm({
+          owner: Option.some(owner),
+          message: "  Confirm removal?  ",
+        }),
+      );
+
+      assert.instanceOf(error, ElectronDialog.ElectronDialogConfirmError);
+      assert.strictEqual(error.ownerWindowId, 9);
+      assert.strictEqual(error.promptLength, "Confirm removal?".length);
+      assert.notProperty(error, "promptMessage");
+      assert.strictEqual(error.cause, cause);
+      assert.include(error.message, "window 9");
+      assert.notInclude(error.message, "Confirm removal?");
+      assert.notInclude(error.message, cause.message);
+    }).pipe(Effect.provide(ElectronDialog.layer)),
+  );
+
+  it.effect("preserves message box request context and cause", () =>
+    Effect.gen(function* () {
+      const cause = new Error("message box failed");
+      showMessageBoxMock.mockRejectedValue(cause);
+      const dialog = yield* ElectronDialog.ElectronDialog;
+
+      const error = yield* Effect.flip(
+        dialog.showMessageBox({
+          type: "warning",
+          title: "Unsaved changes",
+          message: "Discard changes?",
+          detail: "This cannot be undone.",
+          buttons: ["Cancel", "Discard"],
+        }),
+      );
+
+      assert.instanceOf(error, ElectronDialog.ElectronDialogShowMessageBoxError);
+      assert.strictEqual(error.type, "warning");
+      assert.strictEqual(error.titleLength, "Unsaved changes".length);
+      assert.strictEqual(error.messageLength, "Discard changes?".length);
+      assert.strictEqual(error.detailLength, "This cannot be undone.".length);
+      assert.strictEqual(error.buttonCount, 2);
+      assert.notProperty(error, "title");
+      assert.notProperty(error, "dialogMessage");
+      assert.notProperty(error, "dialogDetail");
+      assert.notProperty(error, "buttons");
+      assert.strictEqual(error.cause, cause);
+      assert.include(error.message, "warning");
+      assert.notInclude(error.message, "Unsaved changes");
+      assert.notInclude(error.message, "Discard changes?");
+      assert.notInclude(error.message, "This cannot be undone.");
+      assert.notInclude(error.message, "Cancel");
+      assert.notInclude(error.message, "Discard");
+      assert.notInclude(error.message, cause.message);
+    }).pipe(Effect.provide(ElectronDialog.layer)),
+  );
+
+  it.effect("preserves error box request context and cause in the defect", () =>
+    Effect.gen(function* () {
+      const cause = new Error("error box failed");
+      showErrorBoxMock.mockImplementation(() => {
+        throw cause;
+      });
+      const dialog = yield* ElectronDialog.ElectronDialog;
+
+      const exit = yield* Effect.exit(dialog.showErrorBox("Startup failed", "Could not start."));
+
+      assert.isTrue(exit._tag === "Failure");
+      if (exit._tag === "Success") return;
+      const error = Cause.squash(exit.cause);
+      assert.instanceOf(error, ElectronDialog.ElectronDialogShowErrorBoxError);
+      assert.strictEqual(error.titleLength, "Startup failed".length);
+      assert.strictEqual(error.contentLength, "Could not start.".length);
+      assert.notProperty(error, "title");
+      assert.notProperty(error, "content");
+      assert.strictEqual(error.cause, cause);
+      assert.notInclude(error.message, "Startup failed");
+      assert.notInclude(error.message, "Could not start.");
+      assert.notInclude(error.message, cause.message);
+    }).pipe(Effect.provide(ElectronDialog.layer)),
+  );
 });
diff --git a/apps/desktop/src/electron/ElectronDialog.ts b/apps/desktop/src/electron/ElectronDialog.ts
index 057817ec7e6..be633971bea 100644
--- a/apps/desktop/src/electron/ElectronDialog.ts
+++ b/apps/desktop/src/electron/ElectronDialog.ts
@@ -2,11 +2,80 @@ 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";
 
 const CONFIRM_BUTTON_INDEX = 1;
 
+export class ElectronDialogPickFolderError extends Schema.TaggedErrorClass<ElectronDialogPickFolderError>()(
+  "ElectronDialogPickFolderError",
+  {
+    ownerWindowId: Schema.NullOr(Schema.Number),
+    defaultPath: Schema.NullOr(Schema.String),
+    cause: Schema.Defect(),
+  },
+) {
+  override get message(): string {
+    const owner = this.ownerWindowId === null ? "the application" : `window ${this.ownerWindowId}`;
+    const defaultPath = this.defaultPath === null ? "no default path" : this.defaultPath;
+    return `Failed to open the Electron folder picker for ${owner} with ${defaultPath}.`;
+  }
+}
+
+export class ElectronDialogConfirmError extends Schema.TaggedErrorClass<ElectronDialogConfirmError>()(
+  "ElectronDialogConfirmError",
+  {
+    ownerWindowId: Schema.NullOr(Schema.Number),
+    promptLength: Schema.Number,
+    cause: Schema.Defect(),
+  },
+) {
+  override get message(): string {
+    const owner = this.ownerWindowId === null ? "the application" : `window ${this.ownerWindowId}`;
+    return `Failed to open an Electron confirmation dialog for ${owner} with a ${this.promptLength}-character prompt.`;
+  }
+}
+
+export class ElectronDialogShowMessageBoxError extends Schema.TaggedErrorClass<ElectronDialogShowMessageBoxError>()(
+  "ElectronDialogShowMessageBoxError",
+  {
+    type: Schema.NullOr(Schema.Literals(["none", "info", "error", "question", "warning"])),
+    titleLength: Schema.NullOr(Schema.Number),
+    messageLength: Schema.Number,
+    detailLength: Schema.NullOr(Schema.Number),
+    buttonCount: Schema.Number,
+    cause: Schema.Defect(),
+  },
+) {
+  override get message(): string {
+    const type = this.type === null ? "untyped" : this.type;
+    return `Failed to show the Electron ${type} message box with ${this.buttonCount} buttons.`;
+  }
+}
+
+export class ElectronDialogShowErrorBoxError extends Schema.TaggedErrorClass<ElectronDialogShowErrorBoxError>()(
+  "ElectronDialogShowErrorBoxError",
+  {
+    titleLength: Schema.Number,
+    contentLength: Schema.Number,
+    cause: Schema.Defect(),
+  },
+) {
+  override get message(): string {
+    return `Failed to show the Electron error box with a ${this.titleLength}-character title and ${this.contentLength}-character content.`;
+  }
+}
+
+export const ElectronDialogError = Schema.Union([
+  ElectronDialogPickFolderError,
+  ElectronDialogConfirmError,
+  ElectronDialogShowMessageBoxError,
+  ElectronDialogShowErrorBoxError,
+]);
+export type ElectronDialogError = typeof ElectronDialogError.Type;
+export const isElectronDialogError = Schema.is(ElectronDialogError);
+
 export interface ElectronDialogPickFolderInput {
   readonly owner: Option.Option<Electron.BrowserWindow>;
   readonly defaultPath: Option.Option<string>;
@@ -22,17 +91,24 @@ export class ElectronDialog extends Context.Service<
   {
     readonly pickFolder: (
       input: ElectronDialogPickFolderInput,
-    ) => Effect.Effect<Option.Option<string>>;
-    readonly confirm: (input: ElectronDialogConfirmInput) => Effect.Effect<boolean>;
+    ) => Effect.Effect<Option.Option<string>, ElectronDialogPickFolderError>;
+    readonly confirm: (
+      input: ElectronDialogConfirmInput,
+    ) => Effect.Effect<boolean, ElectronDialogConfirmError>;
     readonly showMessageBox: (
       options: Electron.MessageBoxOptions,
-    ) => Effect.Effect<Electron.MessageBoxReturnValue>;
+    ) => Effect.Effect<Electron.MessageBoxReturnValue, ElectronDialogShowMessageBoxError>;
     readonly showErrorBox: (title: string, content: string) => Effect.Effect<void>;
   }
 >()("@t3tools/desktop/electron/ElectronDialog") {}
 
 export const make = ElectronDialog.of({
   pickFolder: Effect.fn("desktop.electron.dialog.pickFolder")(function* (input) {
+    const ownerWindowId = Option.match(input.owner, {
+      onNone: () => null,
+      onSome: (owner) => owner.id,
+    });
+    const defaultPath = Option.getOrNull(input.defaultPath);
     const openDialogOptions: Electron.OpenDialogOptions = Option.match(input.defaultPath, {
       onNone: () => ({
         properties: ["openDirectory", "createDirectory"],
@@ -42,10 +118,18 @@ export const make = ElectronDialog.of({
         defaultPath,
       }),
     });
-    const result = yield* Option.match(input.owner, {
-      onNone: () => Effect.promise(() => Electron.dialog.showOpenDialog(openDialogOptions)),
-      onSome: (owner) =>
-        Effect.promise(() => Electron.dialog.showOpenDialog(owner, openDialogOptions)),
+    const result = yield* Effect.tryPromise({
+      try: () =>
+        Option.match(input.owner, {
+          onNone: () => Electron.dialog.showOpenDialog(openDialogOptions),
+          onSome: (owner) => Electron.dialog.showOpenDialog(owner, openDialogOptions),
+        }),
+      catch: (cause) =>
+        new ElectronDialogPickFolderError({
+          ownerWindowId,
+          defaultPath,
+          cause,
+        }),
     });
 
     if (result.canceled) {
@@ -67,17 +151,48 @@ export const make = ElectronDialog.of({
       noLink: true,
       message: normalizedMessage,
     };
-    const result = yield* Option.match(input.owner, {
-      onNone: () => Effect.promise(() => Electron.dialog.showMessageBox(options)),
-      onSome: (owner) => Effect.promise(() => Electron.dialog.showMessageBox(owner, options)),
+    const ownerWindowId = Option.match(input.owner, {
+      onNone: () => null,
+      onSome: (owner) => owner.id,
+    });
+    const result = yield* Effect.tryPromise({
+      try: () =>
+        Option.match(input.owner, {
+          onNone: () => Electron.dialog.showMessageBox(options),
+          onSome: (owner) => Electron.dialog.showMessageBox(owner, options),
+        }),
+      catch: (cause) =>
+        new ElectronDialogConfirmError({
+          ownerWindowId,
+          promptLength: normalizedMessage.length,
+          cause,
+        }),
     });
     return result.response === CONFIRM_BUTTON_INDEX;
   }),
-  showMessageBox: (options) => Effect.promise(() => Electron.dialog.showMessageBox(options)),
-  showErrorBox: (title, content) =>
-    Effect.sync(() => {
-      Electron.dialog.showErrorBox(title, content);
+  showMessageBox: (options) =>
+    Effect.tryPromise({
+      try: () => Electron.dialog.showMessageBox(options),
+      catch: (cause) =>
+        new ElectronDialogShowMessageBoxError({
+          type: options.type ?? null,
+          titleLength: options.title?.length ?? null,
+          messageLength: options.message.length,
+          detailLength: options.detail?.length ?? null,
+          buttonCount: options.buttons?.length ?? 0,
+          cause,
+        }),
     }),
+  showErrorBox: (title, content) =>
+    Effect.try({
+      try: () => Electron.dialog.showErrorBox(title, content),
+      catch: (cause) =>
+        new ElectronDialogShowErrorBoxError({
+          titleLength: title.length,
+          contentLength: content.length,
+          cause,
+        }),
+    }).pipe(Effect.orDie),
 });
 
 export const layer = Layer.succeed(ElectronDialog, make);