diff --git a/browse/test/sidebar-ux.test.ts b/browse/test/sidebar-ux.test.ts
index 23bab9bb..328c199e 100644
--- a/browse/test/sidebar-ux.test.ts
+++ b/browse/test/sidebar-ux.test.ts
@@ -1348,6 +1348,30 @@ describe('sidebar auth race prevention', () => {
   });
 });
 
+describe('startup health check fast-retry', () => {
+  const bgSrc = fs.readFileSync(path.join(ROOT, '..', 'extension', 'background.js'), 'utf-8');
+
+  test('initial health check retries every 1s (not 10s)', () => {
+    // The server may not be listening when the extension starts because
+    // Chromium launches before Bun.serve(). A 10s gap means the user
+    // stares at "Connecting..." for 10 seconds. 1s retry fixes this.
+    expect(bgSrc).toContain('startupAttempts');
+    expect(bgSrc).toContain('setInterval(async ()');
+    // Fast retry uses 1000ms, not the 10000ms slow poll
+    expect(bgSrc).toContain('}, 1000);');
+  });
+
+  test('startup retry stops after connection or max attempts', () => {
+    expect(bgSrc).toContain('isConnected || startupAttempts >= 15');
+    expect(bgSrc).toContain('clearInterval(startupCheck)');
+  });
+
+  test('slow 10s polling only starts after startup phase completes', () => {
+    expect(bgSrc).toContain('if (!healthInterval)');
+    expect(bgSrc).toContain('setInterval(checkHealth, 10000)');
+  });
+});
+
 describe('sidebar debug visibility when stuck', () => {
   const spSrc = fs.readFileSync(path.join(ROOT, '..', 'extension', 'sidepanel.js'), 'utf-8');
 
diff --git a/extension/background.js b/extension/background.js
index 516ddb62..d60a5bbd 100644
--- a/extension/background.js
+++ b/extension/background.js
@@ -454,10 +454,25 @@ chrome.tabs.onActivated.addListener((activeInfo) => {
 
 // ─── Startup ────────────────────────────────────────────────────
 
-// Load auth token BEFORE first health poll (token no longer in /health response)
+// Fast-retry health check on startup. The server may not be listening yet
+// (Chromium launches before Bun.serve starts). Retry every 1s for the
+// first 15 seconds, then switch to 10s polling.
 loadAuthToken().then(() => {
   loadPort().then(() => {
-    checkHealth();
-    healthInterval = setInterval(checkHealth, 10000);
+    let startupAttempts = 0;
+    const startupCheck = setInterval(async () => {
+      startupAttempts++;
+      await checkHealth();
+      if (isConnected || startupAttempts >= 15) {
+        clearInterval(startupCheck);
+        // Switch to slow polling now that we're connected (or gave up)
+        if (!healthInterval) {
+          healthInterval = setInterval(checkHealth, 10000);
+        }
+        if (!isConnected) {
+          console.log('[gstack] Startup health checks failed after 15 attempts, falling back to 10s polling');
+        }
+      }
+    }, 1000);
   });
 });