diff --git a/apps/code/src/main/platform-adapters/electron-dialog.test.ts b/apps/code/src/main/platform-adapters/electron-dialog.test.ts
new file mode 100644
index 0000000000..32175b7982
--- /dev/null
+++ b/apps/code/src/main/platform-adapters/electron-dialog.test.ts
@@ -0,0 +1,124 @@
+import { beforeEach, describe, expect, it, vi } from "vitest";
+
+const mockGetFocusedWindow = vi.hoisted(() => vi.fn());
+const mockGetAllWindows = vi.hoisted(() => vi.fn());
+const mockShowOpenDialog = vi.hoisted(() => vi.fn());
+const mockShowMessageBox = vi.hoisted(() => vi.fn());
+
+vi.mock("inversify", () => ({
+  injectable: () => (target: unknown) => target,
+}));
+
+vi.mock("electron", () => ({
+  BrowserWindow: {
+    getFocusedWindow: mockGetFocusedWindow,
+    getAllWindows: mockGetAllWindows,
+  },
+  dialog: {
+    showOpenDialog: mockShowOpenDialog,
+    showMessageBox: mockShowMessageBox,
+  },
+}));
+
+import { ElectronDialog } from "./electron-dialog";
+
+function makeWindow(overrides: { visible?: boolean } = {}) {
+  return {
+    isVisible: vi.fn(() => overrides.visible ?? true),
+    focus: vi.fn(),
+  };
+}
+
+describe("ElectronDialog.pickFile", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    mockShowOpenDialog.mockResolvedValue({
+      canceled: false,
+      filePaths: ["/repo"],
+    });
+  });
+
+  it("parents the picker to the focused window when one exists", async () => {
+    const focused = makeWindow();
+    mockGetFocusedWindow.mockReturnValue(focused);
+
+    const result = await new ElectronDialog().pickFile({ directories: true });
+
+    expect(result).toEqual(["/repo"]);
+    expect(mockShowOpenDialog).toHaveBeenCalledWith(
+      focused,
+      expect.any(Object),
+    );
+    // A focused window is already on top, so we never reach the fallback windows.
+    expect(mockGetAllWindows).not.toHaveBeenCalled();
+  });
+
+  it("falls back to a visible window and focuses it when nothing is focused", async () => {
+    mockGetFocusedWindow.mockReturnValue(null);
+    const hidden = makeWindow({ visible: false });
+    const visible = makeWindow({ visible: true });
+    mockGetAllWindows.mockReturnValue([hidden, visible]);
+
+    await new ElectronDialog().pickFile({ directories: true });
+
+    expect(visible.focus).toHaveBeenCalledTimes(1);
+    // The dialog must be parented to the visible window, not opened unparented
+    // (which is what previously left it stuck behind/off-screen).
+    expect(mockShowOpenDialog).toHaveBeenCalledWith(
+      visible,
+      expect.any(Object),
+    );
+  });
+
+  it("opens unparented only when there are no windows at all", async () => {
+    mockGetFocusedWindow.mockReturnValue(null);
+    mockGetAllWindows.mockReturnValue([]);
+
+    await new ElectronDialog().pickFile({ directories: true });
+
+    expect(mockShowOpenDialog).toHaveBeenCalledWith(expect.any(Object));
+    expect(mockShowOpenDialog.mock.calls[0]).toHaveLength(1);
+  });
+});
+
+describe("ElectronDialog.confirm", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    mockShowMessageBox.mockResolvedValue({ response: 0 });
+  });
+
+  it("parents the message box to the focused window when one exists", async () => {
+    const focused = makeWindow();
+    mockGetFocusedWindow.mockReturnValue(focused);
+
+    await new ElectronDialog().confirm({
+      title: "Discard?",
+      message: "Discard changes?",
+      options: ["Cancel", "Discard"],
+    });
+
+    expect(mockShowMessageBox).toHaveBeenCalledWith(
+      focused,
+      expect.any(Object),
+    );
+  });
+
+  it("falls back to a visible window and focuses it when nothing is focused", async () => {
+    mockGetFocusedWindow.mockReturnValue(null);
+    const hidden = makeWindow({ visible: false });
+    const visible = makeWindow({ visible: true });
+    mockGetAllWindows.mockReturnValue([hidden, visible]);
+
+    await new ElectronDialog().confirm({
+      title: "Discard?",
+      message: "Discard changes?",
+      options: ["Cancel", "Discard"],
+    });
+
+    expect(visible.focus).toHaveBeenCalledTimes(1);
+    expect(mockShowMessageBox).toHaveBeenCalledWith(
+      visible,
+      expect.any(Object),
+    );
+  });
+});
diff --git a/apps/code/src/main/platform-adapters/electron-dialog.ts b/apps/code/src/main/platform-adapters/electron-dialog.ts
index de1fd8f810..6a42dd37f1 100644
--- a/apps/code/src/main/platform-adapters/electron-dialog.ts
+++ b/apps/code/src/main/platform-adapters/electron-dialog.ts
@@ -18,6 +18,25 @@ function severityToType(severity?: DialogSeverity): MessageBoxOptions["type"] {
   return severity ?? "none";
 }
 
+/**
+ * Resolve the window to parent a native dialog to.
+ *
+ * `BrowserWindow.getFocusedWindow()` returns `null` whenever the app has no
+ * focused window — which happens during onboarding flows that hand focus to
+ * external windows (OS auth, the GitHub device-login browser tab, etc.). An
+ * unparented dialog can then open behind the app window or off-screen, looking
+ * completely unresponsive to the user. Fall back to a visible window and focus
+ * it so the dialog is always parented to and rendered on top of a real window.
+ */
+function resolveDialogParent(): BrowserWindow | null {
+  const focused = BrowserWindow.getFocusedWindow();
+  if (focused) return focused;
+  const windows = BrowserWindow.getAllWindows();
+  const parent = windows.find((w) => w.isVisible()) ?? windows[0] ?? null;
+  parent?.focus();
+  return parent;
+}
+
 function buildProperties(options: PickFileOptions): OpenDialogProperty[] {
   const properties: OpenDialogProperty[] = ["treatPackageAsDirectory"];
   if (options.filesAndDirectories) {
@@ -37,7 +56,7 @@ function buildProperties(options: PickFileOptions): OpenDialogProperty[] {
 @injectable()
 export class ElectronDialog implements IDialog {
   public async confirm(options: ConfirmOptions): Promise<number> {
-    const parent = BrowserWindow.getFocusedWindow();
+    const parent = resolveDialogParent();
     const electronOptions: MessageBoxOptions = {
       type: severityToType(options.severity),
       title: options.title,
@@ -54,7 +73,7 @@ export class ElectronDialog implements IDialog {
   }
 
   public async pickFile(options: PickFileOptions): Promise<string[]> {
-    const parent = BrowserWindow.getFocusedWindow();
+    const parent = resolveDialogParent();
     const electronOptions: OpenDialogOptions = {
       title: options.title,
       properties: buildProperties(options),