diff --git a/browse/test/sidepanel-patient-autoconnect.test.ts b/browse/test/sidepanel-patient-autoconnect.test.ts
new file mode 100644
index 000000000..faf38499b
--- /dev/null
+++ b/browse/test/sidepanel-patient-autoconnect.test.ts
@@ -0,0 +1,70 @@
+import { describe, test, expect } from 'bun:test';
+import * as fs from 'fs';
+import * as path from 'path';
+
+// v1.44 patient autoConnect — static-grep invariants for the polling loop.
+//
+// Pre-v1.44 the sidebar gave up at 15s with "Browse server not ready.
+// Reload sidebar to retry." Cold-start the browse server takes ~3-8s on a
+// healthy laptop, longer on Conductor workspaces / slow CI, so the user
+// frequently saw the failure message even when nothing was wrong. The
+// fix: poll forever with ascending status messages and only abort on
+// explicit unrecoverable signals (401 auth invalid).
+
+const CLIENT_JS = path.resolve(
+  new URL(import.meta.url).pathname,
+  '..',
+  '..',
+  '..',
+  'extension',
+  'sidepanel-terminal.js',
+);
+
+describe('sidepanel tryAutoConnect patience (v1.44+)', () => {
+  test('1. no 15s give-up message', () => {
+    const src = fs.readFileSync(CLIENT_JS, 'utf-8');
+    // The v0.x give-up string must NOT reappear — it's the message users
+    // saw on every cold start and the whole point of v1.44 was to delete it.
+    expect(src).not.toContain('Browse server not ready. Reload sidebar to retry.');
+  });
+
+  test('2. ascending status messages at 15s / 60s / 5min', () => {
+    const src = fs.readFileSync(CLIENT_JS, 'utf-8');
+    expect(src).toContain('Waiting for browse server...');
+    expect(src).toContain('Still waiting');
+    expect(src).toContain('still not responding after 5 min');
+  });
+
+  test('3. sticky abort flag prevents loop spam on 401', () => {
+    const src = fs.readFileSync(CLIENT_JS, 'utf-8');
+    expect(src).toContain('autoConnectAborted');
+    // The mint failure branch must short-circuit on 401 specifically.
+    expect(src).toMatch(/minted\.error.*startsWith\('401'\)/);
+    // tryAutoConnect tick must respect the flag.
+    expect(src).toMatch(/if \(autoConnectAborted\) return/);
+  });
+
+  test('4. forceRestart re-arms the loop by clearing the abort flag', () => {
+    const src = fs.readFileSync(CLIENT_JS, 'utf-8');
+    // forceRestart is the user's "try again" escape hatch — must reset
+    // the sticky flag or 401-once means stuck-forever.
+    const block = sliceBetween(src, 'function forceRestart', 'function repaintIfLive');
+    expect(block).toContain('autoConnectAborted = false');
+  });
+
+  test('5. poll interval is 2s, not the legacy 200ms tight loop', () => {
+    const src = fs.readFileSync(CLIENT_JS, 'utf-8');
+    // 200ms ticks burned CPU and made the give-up window land too fast.
+    // 2s is the v1.44 cadence — verify the tight-loop literal is gone.
+    expect(src).toContain('setTimeout(tick, 2000)');
+    expect(src).not.toContain('setTimeout(tick, 200)');
+  });
+});
+
+function sliceBetween(source: string, start: string, end: string): string {
+  const i = source.indexOf(start);
+  if (i === -1) throw new Error(`marker not found: ${start}`);
+  const j = source.indexOf(end, i + start.length);
+  if (j === -1) throw new Error(`end marker not found: ${end}`);
+  return source.slice(i, j);
+}
diff --git a/extension/sidepanel-terminal.js b/extension/sidepanel-terminal.js
index 5e5835d5e..88c3dbb10 100644
--- a/extension/sidepanel-terminal.js
+++ b/extension/sidepanel-terminal.js
@@ -48,6 +48,15 @@
   let term = null;
   let fitAddon = null;
   let ws = null;
+  /**
+   * Sticky abort flag for tryAutoConnect's polling loop. Set when we
+   * receive an unrecoverable signal (auth invalid → 401, claude not
+   * found, fatal server error) so the loop doesn't keep retrying and
+   * spamming the user with the same failure message every 2s. Cleared
+   * by forceRestart() so the user can re-enter the polling loop after
+   * fixing whatever was wrong.
+   */
+  let autoConnectAborted = false;
   /**
    * 25s client-side WS keepalive interval (v1.44+). Belt-and-suspenders with
    * the server-side ping in terminal-agent.ts: server pings cover most
@@ -325,6 +334,16 @@
 
     const minted = await mintSession();
     if (minted.error) {
+      // 401 = stale auth token; no amount of retrying will fix it. Sticky
+      // abort the polling loop so we don't spam the same error every 2s
+      // until the user clicks Restart (which clears the flag).
+      if (typeof minted.error === 'string' && minted.error.startsWith('401')) {
+        autoConnectAborted = true;
+        setState(STATE.IDLE, {
+          message: 'Auth invalid — reload the sidebar or restart your gstack session.',
+        });
+        return;
+      }
       setState(STATE.IDLE, { message: `Cannot start: ${minted.error}` });
       return;
     }
@@ -464,6 +483,9 @@
       term = null;
       fitAddon = null;
     }
+    // User explicitly asked for a fresh start; re-arm the auto-connect
+    // polling loop in case a prior auth failure stuck the abort flag.
+    autoConnectAborted = false;
     setState(STATE.IDLE, { message: 'Starting Claude Code...' });
     tryAutoConnect();
   }
@@ -542,23 +564,47 @@
    * as /health succeeds), then fires connect() automatically. The user
    * doesn't have to press a key — Terminal is the default tab and "tap to
    * start" was a needless paper cut on every reload.
+   *
+   * v1.44 patience overhaul: no more 15s give-up. The user already opened
+   * the sidebar; giving up tells them "you did something wrong" when the
+   * truth is the daemon is slow to boot (or restarting via the upstream
+   * supervisor). We poll forever at 2s intervals with ascending status
+   * messages so the user knows we're still trying, and ONLY abort on
+   * explicit signals: state transition out of IDLE (connect succeeded
+   * or user navigated), or an unrecoverable auth/network signal.
    */
   function tryAutoConnect() {
     if (state !== STATE.IDLE) return;
-    let waited = 0;
+    if (autoConnectAborted) return;
+    const startedAt = Date.now();
     const tick = () => {
       // If the user navigated away (Chat tab) or already connected, drop out.
       if (state !== STATE.IDLE) return;
+      // If a prior attempt hit an unrecoverable error (401, etc.), stop
+      // polling. The user clears the flag by clicking Restart.
+      if (autoConnectAborted) return;
       if (getServerPort() && getAuthToken()) {
         connect();
         return;
       }
-      waited += 200;
-      if (waited > 15000) {
-        setState(STATE.IDLE, { message: 'Browse server not ready. Reload sidebar to retry.' });
-        return;
+      // Ascending status messages — the user wants to know the sidebar is
+      // still trying. Each threshold is the moment the message would
+      // mislead if left silent: at 15s "should have started by now," at
+      // 60s "the server might be in trouble," at 5min "stop waiting and
+      // check on it manually."
+      const elapsed = Date.now() - startedAt;
+      if (elapsed > 300_000) {
+        setState(STATE.IDLE, {
+          message: 'Browse server still not responding after 5 min. Try `$B status` in a terminal.',
+        });
+      } else if (elapsed > 60_000) {
+        setState(STATE.IDLE, {
+          message: 'Still waiting — browse server may be slow to start.',
+        });
+      } else if (elapsed > 15_000) {
+        setState(STATE.IDLE, { message: 'Waiting for browse server...' });
       }
-      setTimeout(tick, 200);
+      setTimeout(tick, 2000);
     };
     tick();
   }