diff --git a/apps/web/src/cloud/connectAuth.tsx b/apps/web/src/cloud/connectAuth.tsx
index 5ad0fb911248..9c74b80d64df 100644
--- a/apps/web/src/cloud/connectAuth.tsx
+++ b/apps/web/src/cloud/connectAuth.tsx
@@ -20,6 +20,11 @@ import { resolveClerkSignInProps } from "../components/clerk/authRedirect";
 import { PrimaryEnvironmentHttpClient } from "../environments/primary/httpClient";
 import { runPrimaryHttp } from "../lib/runtime";
 import { resolveRelayClerkTokenOptions } from "./publicConfig";
+import {
+  isDesktopConnectAuthIdentityPending,
+  shouldRetryDesktopConnectAuthState,
+  startSettledPolling,
+} from "./connectAuthState";
 
 /**
  * One T3 Connect session surface across auth backends. The hosted web app
@@ -29,6 +34,8 @@ import { resolveRelayClerkTokenOptions } from "./publicConfig";
  */
 export interface T3ConnectAuth {
   readonly isLoaded: boolean;
+  /** A legacy desktop credential is waiting for its account id backfill. */
+  readonly isIdentityPending: boolean;
   readonly isSignedIn: boolean;
   readonly userId: string | null;
   /** Account label for display (desktop; web renders Clerk's UserButton). */
@@ -52,6 +59,7 @@ export interface T3ConnectAuth {
 // gates itself on hasCloudPublicConfig, so this is just a safe floor.
 const signedOutAuth: T3ConnectAuth = {
   isLoaded: true,
+  isIdentityPending: false,
   isSignedIn: false,
   userId: null,
   identity: null,
@@ -77,6 +85,7 @@ export function ClerkConnectAuthProvider({ children }: { readonly children: Reac
   const value = useMemo<T3ConnectAuth>(
     () => ({
       isLoaded,
+      isIdentityPending: false,
       isSignedIn: isSignedIn === true,
       userId: userId ?? null,
       identity: null,
@@ -191,11 +200,11 @@ export function DesktopConnectAuthProvider({ children }: { readonly children: Re
   // The bundled server may still be starting when the app mounts; retry until
   // the first state read lands.
   const isLoaded = state !== null;
+  const shouldRetryAuthState = shouldRetryDesktopConnectAuthState(state);
   useEffect(() => {
-    if (isLoaded) return;
-    const interval = setInterval(() => void refresh(), 3_000);
-    return () => clearInterval(interval);
-  }, [isLoaded, refresh]);
+    if (!shouldRetryAuthState) return;
+    return startSettledPolling(refresh, 3_000);
+  }, [refresh, shouldRetryAuthState]);
 
   // The credential is shared with `t3 connect`, so a CLI sign-in or logout
   // can change it while the app is open; re-read when the window regains
@@ -211,8 +220,7 @@ export function DesktopConnectAuthProvider({ children }: { readonly children: Re
   const pendingLogin = state?.pendingLogin ?? false;
   useEffect(() => {
     if (!pendingLogin) return;
-    const interval = setInterval(() => void refresh(), LOGIN_WATCH_INTERVAL_MS);
-    return () => clearInterval(interval);
+    return startSettledPolling(refresh, LOGIN_WATCH_INTERVAL_MS);
   }, [pendingLogin, refresh]);
 
   const getToken = useCallback(async () => {
@@ -266,6 +274,7 @@ export function DesktopConnectAuthProvider({ children }: { readonly children: Re
   const value = useMemo<T3ConnectAuth>(
     () => ({
       isLoaded,
+      isIdentityPending: isDesktopConnectAuthIdentityPending(state),
       // accountId can lag behind authorization for legacy `t3 connect`
       // credentials while the server backfills it; relay features need the
       // account id, so hold "signed in" until it resolves.
diff --git a/apps/web/src/cloud/connectAuthState.test.ts b/apps/web/src/cloud/connectAuthState.test.ts
new file mode 100644
index 000000000000..31fa87081ad4
--- /dev/null
+++ b/apps/web/src/cloud/connectAuthState.test.ts
@@ -0,0 +1,78 @@
+import type { EnvironmentConnectAuthState } from "@t3tools/contracts";
+import { describe, expect, it, vi } from "vite-plus/test";
+
+import {
+  isDesktopConnectAuthIdentityPending,
+  shouldRetryDesktopConnectAuthState,
+  startSettledPolling,
+} from "./connectAuthState";
+
+const authState = (
+  overrides: Partial<EnvironmentConnectAuthState> = {},
+): EnvironmentConnectAuthState => ({
+  authorized: false,
+  pendingLogin: false,
+  authorizationUrl: null,
+  accountId: null,
+  identity: null,
+  ...overrides,
+});
+
+describe("desktop Connect auth state retry", () => {
+  it("retries before the first auth state response arrives", () => {
+    expect(shouldRetryDesktopConnectAuthState(null)).toBe(true);
+  });
+
+  it("retries an authorized legacy credential until its account id is backfilled", () => {
+    expect(shouldRetryDesktopConnectAuthState(authState({ authorized: true }))).toBe(true);
+  });
+
+  it("marks legacy identity backfill without changing stable load states", () => {
+    expect(isDesktopConnectAuthIdentityPending(authState({ authorized: true }))).toBe(true);
+    expect(isDesktopConnectAuthIdentityPending(authState())).toBe(false);
+    expect(
+      isDesktopConnectAuthIdentityPending(authState({ authorized: true, accountId: "user-123" })),
+    ).toBe(false);
+  });
+
+  it("waits for each refresh to settle before scheduling another poll", async () => {
+    vi.useFakeTimers();
+    try {
+      let releaseFirst: (() => void) | undefined;
+      let refreshCount = 0;
+      const refresh = vi.fn(() => {
+        refreshCount += 1;
+        if (refreshCount === 1) {
+          return new Promise<void>((resolve) => {
+            releaseFirst = resolve;
+          });
+        }
+        return Promise.resolve();
+      });
+      const stop = startSettledPolling(refresh, 3_000);
+
+      await vi.advanceTimersByTimeAsync(3_000);
+      expect(refresh).toHaveBeenCalledTimes(1);
+      await vi.advanceTimersByTimeAsync(3_000);
+      expect(refresh).toHaveBeenCalledTimes(1);
+
+      releaseFirst?.();
+      await vi.advanceTimersByTimeAsync(0);
+      await vi.advanceTimersByTimeAsync(2_999);
+      expect(refresh).toHaveBeenCalledTimes(1);
+      await vi.advanceTimersByTimeAsync(1);
+      expect(refresh).toHaveBeenCalledTimes(2);
+
+      stop();
+    } finally {
+      vi.useRealTimers();
+    }
+  });
+
+  it("stops retrying once the state is stable", () => {
+    expect(shouldRetryDesktopConnectAuthState(authState())).toBe(false);
+    expect(
+      shouldRetryDesktopConnectAuthState(authState({ authorized: true, accountId: "user-123" })),
+    ).toBe(false);
+  });
+});
diff --git a/apps/web/src/cloud/connectAuthState.ts b/apps/web/src/cloud/connectAuthState.ts
new file mode 100644
index 000000000000..fff66aebdf5e
--- /dev/null
+++ b/apps/web/src/cloud/connectAuthState.ts
@@ -0,0 +1,36 @@
+import type { EnvironmentConnectAuthState } from "@t3tools/contracts";
+
+export function isDesktopConnectAuthIdentityPending(
+  state: EnvironmentConnectAuthState | null,
+): boolean {
+  return state?.authorized === true && state.accountId === null;
+}
+
+export function startSettledPolling(task: () => Promise<void>, intervalMs: number): () => void {
+  let cancelled = false;
+  let timeout: ReturnType<typeof setTimeout> | undefined;
+
+  const poll = async () => {
+    await task();
+    if (!cancelled) {
+      timeout = setTimeout(poll, intervalMs);
+    }
+  };
+
+  timeout = setTimeout(poll, intervalMs);
+  return () => {
+    cancelled = true;
+    if (timeout !== undefined) {
+      clearTimeout(timeout);
+    }
+  };
+}
+
+export function shouldRetryDesktopConnectAuthState(
+  state: EnvironmentConnectAuthState | null,
+): boolean {
+  // Legacy CLI credentials are authorized before the server lazily backfills
+  // their Clerk account id. Keep polling so the desktop can reach a usable
+  // signed-in state without requiring a focus change or another login.
+  return state === null || isDesktopConnectAuthIdentityPending(state);
+}
diff --git a/apps/web/src/components/cloud/ConnectOnboardingDialog.tsx b/apps/web/src/components/cloud/ConnectOnboardingDialog.tsx
index 2c348c6af727..333999c5d47b 100644
--- a/apps/web/src/components/cloud/ConnectOnboardingDialog.tsx
+++ b/apps/web/src/components/cloud/ConnectOnboardingDialog.tsx
@@ -47,7 +47,7 @@ export function ConnectOnboardingDialog() {
 type OnboardingStep = "publish" | "devices";
 
 function ConfiguredConnectOnboardingDialog() {
-  const { isLoaded, isSignedIn, userId } = useT3ConnectAuth();
+  const { isIdentityPending, isLoaded, isSignedIn, userId } = useT3ConnectAuth();
   const [optOutState, setOptOutState] = useLocalStorage(
     CONNECT_ONBOARDING_OPT_OUT_STORAGE_KEY,
     EMPTY_CONNECT_ONBOARDING_OPT_OUT_STATE,
@@ -94,7 +94,9 @@ function ConfiguredConnectOnboardingDialog() {
   // environments, so each new session starts with no devices to reach. A cold
   // load observes undefined → account and must not re-prompt.
   useEffect(() => {
-    if (!isLoaded) return;
+    // A legacy credential is authorized before its account id is backfilled;
+    // do not record that incomplete snapshot as a signed-out cold load.
+    if (!isLoaded || isIdentityPending) return;
     // A loaded-but-incomplete snapshot (signed in, user id not yet populated)
     // must not be recorded as signed-out — the next render would then look
     // like a fresh sign-in on a cold load.
@@ -105,7 +107,7 @@ function ConfiguredConnectOnboardingDialog() {
     if (previousAccount !== undefined && previousAccount !== nextAccount && nextAccount !== null) {
       setRequestedAccount(nextAccount);
     }
-  }, [isLoaded, isSignedIn, userId]);
+  }, [isIdentityPending, isLoaded, isSignedIn, userId]);
 
   // A manageable session implies a primary environment, so when the scopes
   // allow publishing, wait for the connection target too — otherwise the