diff --git a/frontend/src/App.test.tsx b/frontend/src/App.test.tsx
index 7574e7e..6eb008f 100644
--- a/frontend/src/App.test.tsx
+++ b/frontend/src/App.test.tsx
@@ -84,6 +84,10 @@ import { App } from './App';
 beforeEach(() => {
   window.localStorage.clear();
   window.location.hash = '';
+  Object.defineProperty(navigator, 'usb', {
+    configurable: true,
+    value: {},
+  });
   checkProvisionedMock.mockResolvedValue(false);
   ensureAnisetteMock.mockResolvedValue({ anisetteData: fakeAnisette, provisioned: true });
   loginAccountMock.mockResolvedValue(fakeContext);
@@ -115,6 +119,35 @@ describe('App — page + nav', () => {
   });
 });
 
+describe('App — pairing modal', () => {
+  it('keeps trust pending separate from paired success and retries cleanly', async () => {
+    const pendingError = new Error('Pair error=PairingDialogResponsePending');
+    pairDeviceFlowMock
+      .mockImplementationOnce(async (ctx) => {
+        ctx.onTrustPending();
+        throw pendingError;
+      })
+      .mockResolvedValueOnce({ udid: 'UDID-TEST', name: 'iPhone' });
+    isPairingDialogPendingErrorMock.mockImplementation(
+      (error) => error === pendingError || String(error).includes('PairingDialogResponsePending'),
+    );
+
+    render(<App />);
+    await userEvent.click(screen.getByRole('button', { name: /Sign & Install/ }));
+    await userEvent.click(screen.getByRole('button', { name: 'Connect Device' }));
+
+    expect(await screen.findByText('Trust This Device')).toBeInTheDocument();
+    expect(screen.queryByText('Device Paired')).toBeNull();
+
+    await userEvent.click(screen.getByRole('button', { name: 'I Trusted This Device' }));
+    expect(await screen.findByText('Device Paired')).toBeInTheDocument();
+    await waitFor(() => expect(pairDeviceFlowMock).toHaveBeenCalledTimes(2));
+
+    await userEvent.click(screen.getByRole('button', { name: 'Continue' }));
+    expect(screen.queryByText('Device Paired')).toBeNull();
+  });
+});
+
 describe('App — login modal', () => {
   it('opens login modal on Add Account, then logs in and navigates to sign', async () => {
     render(<App />);
diff --git a/frontend/src/App.tsx b/frontend/src/App.tsx
index d73c973..8f9a0e0 100644
--- a/frontend/src/App.tsx
+++ b/frontend/src/App.tsx
@@ -7,7 +7,7 @@ import { Header, type AppPage } from './components/Header';
 import { LoginPage } from './components/LoginPage';
 import { LoginModal } from './components/LoginModal';
 import { SignPage } from './components/SignPage';
-import { TrustModal } from './components/TrustModal';
+import { TrustModal, type TrustModalState } from './components/TrustModal';
 import { TwoFactorModal } from './components/TwoFactorModal';
 import { ProgressCard } from './components/ProgressCard';
 
@@ -42,6 +42,7 @@ import { useLog } from './lib/use-log';
 
 const LOGIN_PAGE_HASH = '#/login';
 const SIGN_PAGE_HASH = '#/sign';
+const TRUST_MODAL_CLOSED: TrustModalState = 'closed';
 
 type BusyState = {
   pair: boolean;
@@ -50,6 +51,11 @@ type BusyState = {
   install: boolean;
 };
 
+type PairFlowResult =
+  | { kind: 'paired'; info: PairedDeviceInfo }
+  | { kind: 'pending' }
+  | { kind: 'failed' };
+
 const idleBusy: BusyState = { pair: false, loginSign: false, sign: false, install: false };
 
 function resolvePageFromHash(hash: string): AppPage {
@@ -105,7 +111,7 @@ export function App() {
   const lastInstallPercentRef = useRef<number>(0);
 
   // Modals
-  const [trustOpen, setTrustOpen] = useState<boolean>(false);
+  const [trustState, setTrustState] = useState<TrustModalState>(TRUST_MODAL_CLOSED);
   const [twoFactor, setTwoFactor] = useState<{
     open: boolean;
     submit: ((code: string) => void) | null;
@@ -131,6 +137,7 @@ export function App() {
   const activeAccountKey = loginContext ? accountKey(loginContext.appleId, loginContext.team.identifier) : null;
 
   const cachedAccountKeys = useMemo(() => new Set(accountContextMapRef.current.keys()), [savedAccounts, loginContext]);
+  const trustOpen = trustState !== TRUST_MODAL_CLOSED;
 
   // ---- log + progress plumbing ----
   const addLog = useCallback(
@@ -259,17 +266,25 @@ export function App() {
   }, [knownUdids, selectedTargetUdid]);
 
   // ---- pair flow ----
-  const handlePair = useCallback(async (): Promise<PairedDeviceInfo | null> => {
-    if (busyRef.current.pair) return null;
+  /**
+   * lockdownd can return PairingDialogResponsePending before the on-device trust sheet is resolved.
+   * Keep that state separate so the UI never renders "paired" until pairDevice + startSession both finish.
+   */
+  const runPairFlow = useCallback(async (options: {
+    showSuccess: boolean;
+    startLogMessage: string;
+  }): Promise<PairFlowResult> => {
+    if (busyRef.current.pair) return { kind: 'failed' };
     setBusy((prev) => ({ ...prev, pair: true }));
-    setTrustOpen(true);
-    addLog('pair: please continue on your device');
+    setTrustState('pairing');
+    addLog(options.startLogMessage);
     try {
       const info = await pairDeviceFlow({
         log: addLog,
         clientRef: directClientRef,
         onStateChange: () => {},
         onTrustPending: () => {
+          setTrustState('pending');
           addLog('pair: waiting for trust confirmation on device');
         },
       });
@@ -279,20 +294,34 @@ export function App() {
       setSelectedTargetUdid(info.udid);
       saveText(SELECTED_DEVICE_UDID_STORAGE_KEY, info.udid);
       setPairRecordsVersion((v) => v + 1);
-      setTrustOpen(false);
-      return info;
+      setTrustState(options.showSuccess ? 'paired' : TRUST_MODAL_CLOSED);
+      return { kind: 'paired', info };
     } catch (error) {
       if (isPairingDialogPendingError(error)) {
-        return null;
+        return { kind: 'pending' };
       }
-      setTrustOpen(false);
+      setTrustState(TRUST_MODAL_CLOSED);
       addLog(`pair failed: ${formatError(error)}`);
-      return null;
+      return { kind: 'failed' };
     } finally {
       setBusy((prev) => ({ ...prev, pair: false }));
     }
   }, [addLog]);
 
+  const handlePair = useCallback(() => {
+    void runPairFlow({
+      showSuccess: true,
+      startLogMessage: 'pair: please continue on your device',
+    });
+  }, [runPairFlow]);
+
+  const handleTrustRetry = useCallback(() => {
+    void runPairFlow({
+      showSuccess: true,
+      startLogMessage: 'pair: retrying after trust confirmation',
+    });
+  }, [runPairFlow]);
+
   // ---- login flow ----
   const handleLogin = useCallback(async () => {
     if (busyRef.current.loginSign) return;
@@ -433,12 +462,24 @@ export function App() {
         log: addLog,
         clientRef: directClientRef,
         onStateChange: () => {},
-        onTrustPending: () => setTrustOpen(true),
+        onTrustPending: () => setTrustState('pending'),
       });
       let currentDeviceUdid = pairedDeviceInfo?.udid ?? null;
       if (!client.isSessionStarted) {
-        const freshInfo = await handlePair();
-        currentDeviceUdid = freshInfo?.udid ?? null;
+        const pairResult = await runPairFlow({
+          showSuccess: false,
+          startLogMessage: 'install: device trust required, continue on your device',
+        });
+        if (pairResult.kind === 'pending') {
+          addLog('install paused: finish trusting the device, then install again');
+          setProgress({ percent: 0, status: 'idle' });
+          return;
+        }
+        if (pairResult.kind === 'failed') {
+          setProgress({ percent: 0, status: 'failed' });
+          return;
+        }
+        currentDeviceUdid = pairResult.info.udid;
       }
       if (currentDeviceUdid !== targetUdid) {
         throw new Error('connected device udid does not match selected target');
@@ -457,7 +498,7 @@ export function App() {
     } finally {
       setBusy((prev) => ({ ...prev, install: false }));
     }
-  }, [addLog, handlePair, pairedDeviceInfo, prepared, selectedIpaFile, selectedTargetUdid]);
+  }, [addLog, pairedDeviceInfo, prepared, runPairFlow, selectedIpaFile, selectedTargetUdid]);
 
   // ---- switch account ----
   const handleSwitchAccount = useCallback(
@@ -620,7 +661,11 @@ export function App() {
         onDismiss={handleDismissProgress}
       />
 
-      <TrustModal open={trustOpen} onClose={() => setTrustOpen(false)} pairing={busy.pair} />
+      <TrustModal
+        state={trustState}
+        onClose={() => setTrustState(TRUST_MODAL_CLOSED)}
+        onRetry={handleTrustRetry}
+      />
       <TwoFactorModal
         open={twoFactor.open}
         onSubmit={handleTwoFactorSubmit}
diff --git a/frontend/src/components/TrustModal.test.tsx b/frontend/src/components/TrustModal.test.tsx
index 51e8faa..97c2e16 100644
--- a/frontend/src/components/TrustModal.test.tsx
+++ b/frontend/src/components/TrustModal.test.tsx
@@ -5,20 +5,31 @@ import { TrustModal } from './TrustModal';
 
 describe('TrustModal', () => {
   it('is hidden when closed', () => {
-    const { container } = render(<TrustModal open={false} onClose={() => {}} pairing={false} />);
+    const { container } = render(<TrustModal state="closed" onClose={() => {}} onRetry={() => {}} />);
     const modal = container.querySelector('.modal');
-    expect(modal).toHaveAttribute('aria-hidden', 'true');
+    expect(modal).toBeNull();
   });
 
   it('shows pairing state with spinner when pairing', () => {
-    render(<TrustModal open onClose={() => {}} pairing />);
+    render(<TrustModal state="pairing" onClose={() => {}} onRetry={() => {}} />);
     expect(screen.getByText('Continue on Your Device')).toBeInTheDocument();
     expect(screen.getByText('Waiting for device…')).toBeInTheDocument();
   });
 
+  it('shows pending state with retry and close actions', async () => {
+    const onClose = vi.fn();
+    const onRetry = vi.fn();
+    render(<TrustModal state="pending" onClose={onClose} onRetry={onRetry} />);
+    expect(screen.getByText('Trust This Device')).toBeInTheDocument();
+    await userEvent.click(screen.getByRole('button', { name: 'I Trusted This Device' }));
+    expect(onRetry).toHaveBeenCalledTimes(1);
+    await userEvent.click(screen.getByRole('button', { name: 'Close' }));
+    expect(onClose).toHaveBeenCalledTimes(1);
+  });
+
   it('shows success state with Continue button when paired', async () => {
     const onClose = vi.fn();
-    render(<TrustModal open onClose={onClose} pairing={false} />);
+    render(<TrustModal state="paired" onClose={onClose} onRetry={() => {}} />);
     expect(screen.getByText('Device Paired')).toBeInTheDocument();
     await userEvent.click(screen.getByRole('button', { name: 'Continue' }));
     expect(onClose).toHaveBeenCalledTimes(1);
diff --git a/frontend/src/components/TrustModal.tsx b/frontend/src/components/TrustModal.tsx
index 8cfa1a0..df22823 100644
--- a/frontend/src/components/TrustModal.tsx
+++ b/frontend/src/components/TrustModal.tsx
@@ -1,14 +1,25 @@
+import { Button } from './ui/Button';
 import { Modal } from './ui/Modal';
 
+export type TrustModalState = 'closed' | 'pairing' | 'pending' | 'paired';
+
 interface TrustModalProps {
-  open: boolean;
+  state: TrustModalState;
   onClose: () => void;
-  pairing: boolean;
+  onRetry: () => void;
 }
 
-export function TrustModal({ open, onClose, pairing }: TrustModalProps) {
+export function TrustModal({ state, onClose, onRetry }: TrustModalProps) {
+  if (state === 'closed') return null;
+
   return (
-    <Modal open={open} onClose={onClose} labelledBy="trust-title" closeOnBackdrop={false} closeOnEscape={!pairing}>
+    <Modal
+      open
+      onClose={onClose}
+      labelledBy="trust-title"
+      closeOnBackdrop={false}
+      closeOnEscape={state !== 'pairing'}
+    >
       <div className="flex flex-col items-center text-center">
         <div className="mb-4 flex h-14 w-14 items-center justify-center rounded-full bg-surface" aria-hidden="true">
           <svg
@@ -26,7 +37,7 @@ export function TrustModal({ open, onClose, pairing }: TrustModalProps) {
           </svg>
         </div>
 
-        {pairing ? (
+        {state === 'pairing' ? (
           <>
             <h2 id="trust-title" className="text-[16px] font-semibold tracking-tight text-ink">
               Continue on Your Device
@@ -43,15 +54,35 @@ export function TrustModal({ open, onClose, pairing }: TrustModalProps) {
               <span>Waiting for device…</span>
             </div>
           </>
+        ) : state === 'pending' ? (
+          <>
+            <h2 id="trust-title" className="text-[16px] font-semibold tracking-tight text-ink">
+              Trust This Device
+            </h2>
+            <p className="mt-2 text-[13px] leading-[1.6] text-muted">
+              Approve the trust prompt on your iPhone or iPad, then return here to finish pairing.
+            </p>
+            <p className="mt-1.5 text-[12px] leading-[1.5] text-subtle">
+              Tap <strong className="font-semibold text-ink">Trust</strong> and enter your passcode if asked.
+            </p>
+            <div className="mt-5 grid w-full gap-2 sm:grid-cols-2">
+              <Button variant="ghost" onClick={onClose} className="w-full">
+                Close
+              </Button>
+              <Button variant="primary" onClick={onRetry} className="w-full">
+                I Trusted This Device
+              </Button>
+            </div>
+          </>
         ) : (
           <>
             <h2 id="trust-title" className="text-[16px] font-semibold tracking-tight text-ink">
               Device Paired
             </h2>
             <p className="mt-2 text-[13px] leading-[1.6] text-muted">Your device is connected and ready for signing.</p>
-            <button type="button" onClick={onClose} className="btn btn-primary mt-5 w-full">
+            <Button variant="primary" onClick={onClose} className="mt-5 w-full">
               Continue
-            </button>
+            </Button>
           </>
         )}
       </div>