diff --git a/components/settings/chatgpt-connection.tsx b/components/settings/chatgpt-connection.tsx
index a87d06d..3e368dd 100644
--- a/components/settings/chatgpt-connection.tsx
+++ b/components/settings/chatgpt-connection.tsx
@@ -21,7 +21,7 @@ function isStatus(value: unknown): value is ChatGPTStatus {
 	const s = value as ChatGPTStatus;
 	return typeof s.available === "boolean" && typeof s.pending === "boolean" && typeof s.allowBackgroundUse === "boolean" && (s.activeId === null || typeof s.activeId === "string") &&
 		(s.error === null || typeof s.error === "string") && (s.catalogError == null || typeof s.catalogError === "string") && Array.isArray(s.accounts) &&
-		s.accounts.every((a) => a && typeof a.id === "string" && typeof a.email === "string" && typeof a.registration === "string" && typeof a.connected === "boolean" && (a.planEnabled === undefined || typeof a.planEnabled === "boolean"));
+		s.accounts.every((a) => a && typeof a.id === "string" && typeof a.email === "string" && typeof a.registration === "string" && typeof a.connected === "boolean" && (a.planEnabled === undefined || typeof a.planEnabled === "boolean") && (a.canSignInAgain === undefined || typeof a.canSignInAgain === "boolean"));
 }
 function replyError(value: unknown): string {
 	return value && typeof value === "object" && "error" in value && typeof value.error === "string" ? value.error : CONTROL_ERROR;
@@ -304,7 +304,7 @@ export function ChatGPTUIProvider({ children }: { children: React.ReactNode }) {
 				<ConnectionFooter testid="chatgpt-account-footer" leading={dialog.kind === "manage" && <div data-testid="chatgpt-account-actions">
 					<Button variant="ghost" size="sm" className="cursor-pointer text-red-400 hover:bg-red-500/10 hover:text-red-300" data-testid="chatgpt-disconnect" disabled={busy || status.pending || !managedPresent} onClick={() => showDialog({ ...dialog, confirm: true })}>Disconnect</Button>
 				</div>}>
-					{dialog.kind === "manage" && managedPresent && managed && !managed.connected && status.available && <Button variant="outline" size="sm" disabled={busy || status.pending || !status.available} onClick={() => openConnect(managed.id)}>Sign in again</Button>}
+					{dialog.kind === "manage" && managedPresent && managed && !managed.connected && managed.canSignInAgain === true && status.available && <Button variant="outline" size="sm" disabled={busy || status.pending || !status.available} onClick={() => openConnect(managed.id)}>Sign in again</Button>}
 					<Button variant={dialog.kind === "manage" ? "outline" : "ghost"} size="sm" onClick={close} disabled={busy && operation.current !== "login"}>{dialog.kind === "connect" ? "Cancel" : "Close"}</Button>
 					{dialog.kind === "connect" && <ContinueButton onClick={() => void login()} disabled={!status.available || busy || status.pending} testid="chatgpt-proceed" />}
 				</ConnectionFooter>
diff --git a/electron/chatgpt.cjs b/electron/chatgpt.cjs
index a56825d..6b3c6e9 100644
--- a/electron/chatgpt.cjs
+++ b/electron/chatgpt.cjs
@@ -194,6 +194,9 @@ function createChatGPT({ store, openExternal, fetch: request = globalThis.fetch,
 					registration: r.clientId,
 					connected: !storageDenied && !closed && !paused && !suspended && !r.reconnectRequired && planScopes(r.tokens),
 					planEnabled: !storageDenied && !r.reconnectRequired && planScopes(r.tokens),
+					// Recovery is authorization-only, not a response to storage failure
+					// or temporary transport suspension. Never infer it from error copy.
+					canSignInAgain: !storageDenied && !closed && !paused && (r.reconnectRequired === true || !planScopes(r.tokens)),
 				};
 			}),
 			error: lastError,
diff --git a/src/core/contracts/chatgpt.ts b/src/core/contracts/chatgpt.ts
index ad0ee72..6bc68d9 100644
--- a/src/core/contracts/chatgpt.ts
+++ b/src/core/contracts/chatgpt.ts
@@ -5,7 +5,12 @@ export interface ChatGPTStatus {
 	/** App-wide ChatGPT background permission, independent of account selection. */
 	allowBackgroundUse: boolean;
 	activeId: string | null;
-	accounts: { id: string; email: string; registration: string; connected: boolean; planEnabled?: boolean }[];
+	accounts: {
+		id: string; email: string; registration: string; connected: boolean; planEnabled?: boolean;
+		/** Main-owned authorization recovery eligibility. Missing means unknown, not eligible.
+		 * False for storage failures, paused/closed connections, and healthy authorization. */
+		canSignInAgain?: boolean;
+	}[];
 	error: string | null;
 	catalogError?: string | null;
 }
diff --git a/tests/chatgpt-connection-ui.test.tsx b/tests/chatgpt-connection-ui.test.tsx
index d685900..f5f8f74 100644
--- a/tests/chatgpt-connection-ui.test.tsx
+++ b/tests/chatgpt-connection-ui.test.tsx
@@ -17,7 +17,7 @@ const dom = parseHTML("<html><body></body></html>");
 Object.assign(globalThis, { window: dom.window, document: dom.document, Element: dom.window.Element, HTMLElement: dom.window.HTMLElement, CustomEvent: dom.window.CustomEvent, IS_REACT_ACT_ENVIRONMENT: true, localStorage: { getItem: () => null, setItem() {} } });
 const originalFetch = globalThis.fetch;
 let root: Root | undefined, host: HTMLDivElement | undefined;
-const account = (id = "private-registration-id", email = "learner@example.invalid", connected = true) => ({ id, email, registration: "private-issued-client", connected, planEnabled: connected });
+const account = (id = "private-registration-id", email = "learner@example.invalid", connected = true) => ({ id, email, registration: "private-issued-client", connected, planEnabled: connected, canSignInAgain: !connected });
 const disconnected = (allowBackgroundUse = true): ChatGPTStatus => ({ available: true, pending: false, allowBackgroundUse, activeId: null, accounts: [account("signed-out-record", "signed-out@example.invalid", false)], error: null });
 const connected = (allowBackgroundUse = true): ChatGPTStatus => ({ ...disconnected(allowBackgroundUse), activeId: "private-registration-id", accounts: [account(), ...disconnected().accounts] });
 const storageError = "ChatGPT credentials could not be read or saved. Check local file access, then reconnect before making requests.";
@@ -42,6 +42,16 @@ function fixture(initial = disconnected(), overrides: Partial<ChatGPTControlBrid
  window.lh = { expandWindow() {}, chatgpt: bridge };
  return { calls, bridge, push, get status() { return status; }, complete() { push({ ...connected(status.allowBackgroundUse), pending: false }); } };
 }
+function recoveryController({ writeFails = false, tokens = "valid" }: { writeFails?: boolean; tokens?: "valid" | "missing" | "restricted" | "scope" | "expired" } = {}) {
+ const require = createRequire(import.meta.url); const { createChatGPT, SCOPES } = require("../electron/chatgpt.cjs"); const { chatGPTControl } = require("../electron/chatgpt-ipc.cjs");
+ const registration: any = { id: "fixture", clientId: "oaiapp_fixture", issuer: "https://auth.openai.com", subject: "fixture", email: "fixture@example.invalid", tokens: { accessToken: "fake-access", refreshToken: "fake-refresh", idToken: "fake-id", expiresAt: tokens === "expired" ? 0 : Date.now() + 3600000, scopes: tokens === "scope" ? ["openid"] : [...SCOPES] } };
+ if (tokens === "missing") delete registration.tokens; if (tokens === "restricted") registration.reconnectRequired = true;
+ let saved = { version: 1, hostId: "urn:uuid:offline-recovery", activeId: "fixture", allowBackgroundUse: true, registrations: [registration] };
+ let browserAttempts = 0, tokenRequests = 0; const listeners = new Set<() => void>();
+ const service = createChatGPT({ store: { read: async () => structuredClone(saved), write: async (next: typeof saved) => { if (writeFails) throw Object.assign(new Error("fake-storage-failure"), { code: "storage" }); saved = structuredClone(next); } }, openExternal: () => { browserAttempts++; throw new Error("No real browser"); }, fetch: async (url: string) => { tokenRequests++; assert.equal(tokens, "expired"); assert.equal(url, "https://auth.openai.com/api/accounts/oauth/token"); return Response.json({ error: "invalid_grant" }, { status: 401 }); }, onChange: () => { for (const cb of listeners) cb(); } });
+ window.lh = { expandWindow() {}, chatgpt: { status: () => chatGPTControl({ op: "status" }, service), consent: (enabled) => chatGPTControl({ op: "consent", enabled }, service), login: (id) => chatGPTControl({ op: "login", id }, service), cancel: () => chatGPTControl({ op: "cancel" }, service), select: (id) => chatGPTControl({ op: "select", id }, service), disconnect: (id) => chatGPTControl({ op: "disconnect", id }, service), logout: (id) => chatGPTControl({ op: "logout", id }, service), onChange: (cb) => { listeners.add(cb); return () => listeners.delete(cb); } } };
+ return { service, get saved() { return saved; }, get browserAttempts() { return browserAttempts; }, get tokenRequests() { return tokenRequests; } };
+}
 async function mount(children: React.ReactNode = <ChatGPTConnection />) {
  host = document.createElement("div"); document.body.append(host); root = createRoot(host);
  await act(async () => root!.render(<ChatGPTUIProvider>{children}</ChatGPTUIProvider>));
@@ -249,6 +259,55 @@ test("ChatGPT Sign in again is reserved for a saved disconnected account and kee
  await click(byTest("chatgpt-proceed")); assert.deepEqual(f.calls.login, ["signed-out-record"]); assert.equal(f.status.activeId, "private-registration-id");
  await click(button("Cancel", byTest("chatgpt-account-dialog"))); assert.equal(f.calls.cancel, 1); assert.deepEqual(f.calls.disconnect, []); assert.deepEqual(f.calls.consent, []);
 });
+test("actual controller storage-write failure is not ChatGPT authorization recovery even while available stays true", async () => {
+ const f = recoveryController({ writeFails: true });
+ try {
+  await mount(); await click(button("Manage…")); assert(!button("Sign in again")); await click(toggle());
+  const status = await f.service.status(); assert.equal(status.available, true); assert.equal(status.pending, false); assert.equal(status.accounts[0].connected, false); assert.equal(status.accounts[0].planEnabled, false); assert.equal(status.error, storageError);
+  assert(!button("Sign in again"), "a failed credential write must not offer reauthorization");
+  assert.equal(status.accounts[0].canSignInAgain, false); assert.equal(f.browserAttempts, 0); assert.equal(f.tokenRequests, 0);
+ } finally { await act(async () => f.service.close()); }
+});
+for (const tokens of ["missing", "restricted", "scope"] as const) test(`actual controller ${tokens} authorization permits recovery, but paused/closed state does not`, async () => {
+ const f = recoveryController({ tokens });
+ try {
+  await mount(); await click(byTest("chatgpt-login")); await selectAccount("Saved ChatGPT account", "fixture"); await click(button("Manage…"));
+  assert.equal((await f.service.status()).accounts[0].canSignInAgain, true); assert(button("Sign in again"));
+  assert.equal(f.saved.registrations[0].canSignInAgain, undefined, "eligibility is projected, never persisted");
+  await act(async () => f.service.pause()); assert.equal((await f.service.status()).accounts[0].canSignInAgain, false); assert(!button("Sign in again"));
+  await act(async () => f.service.resume()); assert.equal((await f.service.status()).accounts[0].canSignInAgain, true); assert(button("Sign in again"));
+  await act(async () => f.service.close()); assert.equal((await f.service.status()).accounts[0].canSignInAgain, false); assert(!button("Sign in again"));
+  assert.equal(f.browserAttempts, 0); assert.equal(f.tokenRequests, 0);
+ } finally { await act(async () => f.service.close()); }
+});
+test("storage denial overrides an otherwise eligible remembered ChatGPT authorization recovery", async () => {
+ const f = recoveryController({ tokens: "missing", writeFails: true });
+ try {
+  await mount(); await click(byTest("chatgpt-login")); await selectAccount("Saved ChatGPT account", "fixture"); await click(button("Manage…")); assert(button("Sign in again"));
+  await click(toggle()); const status = await f.service.status(); assert.equal(status.available, true); assert.equal(status.error, storageError); assert.equal(status.accounts[0].canSignInAgain, false); assert(!button("Sign in again"));
+  assert.equal(f.browserAttempts, 0); assert.equal(f.tokenRequests, 0);
+ } finally { await act(async () => f.service.close()); }
+});
+test("actual invalid_grant recovery preserves remembered identity and stages the existing registration flow", async () => {
+ const f = recoveryController({ tokens: "expired" });
+ try {
+  await mount(); await click(button("Manage…")); assert.equal((await f.service.status()).accounts[0].canSignInAgain, false); assert(!button("Sign in again"));
+  await act(async () => { await f.service.models(); });
+  const status = await f.service.status(); assert.equal(status.available, true); assert.equal(status.accounts[0].connected, false); assert.equal(status.accounts[0].canSignInAgain, true);
+  assert.equal(status.accounts[0].id, "fixture"); assert.equal(status.accounts[0].registration, "oaiapp_fixture"); assert.equal(f.saved.registrations[0].tokens, undefined);
+  await click(button("Sign in again")); assert(byTest("chatgpt-privacy-notice")); assert(toggle()); assert.equal(document.querySelector<HTMLSelectElement>('select[aria-label="Saved ChatGPT account"]')?.value, "fixture");
+  assert.equal(f.tokenRequests, 1, "only the injected refresh response was requested"); assert.equal(f.browserAttempts, 0, "staging recovery never starts OAuth");
+ } finally { await act(async () => f.service.close()); }
+});
+test("missing eligibility remains compatible but never implies authorization recovery; malformed eligibility is rejected", async () => {
+ const initial = connected(); initial.accounts = [account()]; const f = fixture(initial); await mount(); await click(button("Manage…"));
+ const legacy: ChatGPTStatus = { ...initial, accounts: initial.accounts.map(({ canSignInAgain: _ignored, ...a }) => ({ ...a, connected: false, planEnabled: false })) };
+ await act(async () => f.push(legacy)); assert(!button("Sign in again")); assert(!document.querySelector('[role="alert"]'));
+ for (const value of [null, "true", 1]) {
+  await act(async () => f.push({ ...legacy, accounts: legacy.accounts.map((a) => ({ ...a, canSignInAgain: value })) } as unknown as ChatGPTStatus));
+  assert(!button("Sign in again")); assert.equal(document.querySelector('[role="alert"]')?.textContent, "The ChatGPT connection could not be changed. Try again.");
+ }
+});
 test("connected setup row retains the email dropdown before muted Manage", async () => {
  fixture(connected()); await mount(<ChatGPTConnection setup />);
  const row = byTest("chatgpt-connection").firstElementChild!; assert.equal(row.children[1]!.tagName, "SELECT"); assert.equal(row.children[2]!.textContent, "Manage…"); assert.match(row.children[2]!.className, /text-muted-foreground/);