diff --git a/web/src/AuthCallback.tsx b/web/src/AuthCallback.tsx
index af7dfdc1..a15ff54b 100644
--- a/web/src/AuthCallback.tsx
+++ b/web/src/AuthCallback.tsx
@@ -25,7 +25,7 @@ export function AuthCallback() {
   // a brand new flow rather than reuse what is left in the URL or session storage.
   function retry() {
     window.history.replaceState(null, "", "/auth/callback");
-    startLogin();
+    startLogin(sessionStorage.getItem("sotto_oauth_destination") ?? "/app");
   }
 
   return (
diff --git a/web/src/__tests__/AuthCallbackRetry.test.tsx b/web/src/__tests__/AuthCallbackRetry.test.tsx
new file mode 100644
index 00000000..b74dbc36
--- /dev/null
+++ b/web/src/__tests__/AuthCallbackRetry.test.tsx
@@ -0,0 +1,43 @@
+import "@testing-library/jest-dom/vitest";
+import { cleanup, fireEvent, render, screen } from "@testing-library/react";
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+
+import { AuthCallback } from "../AuthCallback";
+
+describe("AuthCallback retry destination", () => {
+  beforeEach(() => {
+    sessionStorage.clear();
+    window.history.replaceState(null, "", "/auth/callback?state=stale-state");
+  });
+
+  afterEach(() => {
+    cleanup();
+    vi.restoreAllMocks();
+  });
+
+  it.each([
+    ["/cloud", "/cloud"],
+    ["/app", "/app"],
+    [null, "/app"],
+    ["https://example.com", "/app"],
+  ])("starts a fresh login for stored destination %s", (stored, expected) => {
+    const freshState = "00000000-0000-4000-8000-000000000003";
+    vi.spyOn(crypto, "randomUUID").mockReturnValue(freshState);
+    const assign = vi.spyOn(window.location, "assign").mockImplementation(() => {});
+    sessionStorage.setItem("sotto_oauth_state", "expected-state");
+    if (stored !== null) sessionStorage.setItem("sotto_oauth_destination", stored);
+
+    render(<AuthCallback />);
+    expect(screen.getByRole("alert")).toHaveTextContent("state mismatch");
+    fireEvent.click(screen.getByRole("button", { name: "Try again" }));
+
+    expect(window.location.pathname + window.location.search).toBe("/auth/callback");
+    expect(sessionStorage.getItem("sotto_oauth_state")).toBe(freshState);
+    expect(sessionStorage.getItem("sotto_oauth_destination")).toBe(expected);
+    expect(assign).toHaveBeenCalledTimes(1);
+    const redirect = new URL(String(assign.mock.calls[0][0]), window.location.origin);
+    expect(redirect.pathname).toBe("/auth/github/login");
+    expect(redirect.searchParams.get("state")).toBe(freshState);
+    expect(redirect.searchParams.get("redirect_uri")).toBe(window.location.origin + "/auth/callback");
+  });
+});