diff --git a/skill/scripts/live-browser.js b/skill/scripts/live-browser.js
index 277c60e2c..ac6f18586 100644
--- a/skill/scripts/live-browser.js
+++ b/skill/scripts/live-browser.js
@@ -7834,7 +7834,6 @@
     if (editBadgeEl && editBadgeEl.style.display !== 'none') renderEditBadge('idle-disabled');
     showBar('generating');
     saveSession();
-    sendCheckpoint('generate_started');
     writeScrollY(window.scrollY);
     if (variantObserver) variantObserver.disconnect();
     variantObserver = startVariantObserver(currentSessionId);
@@ -7916,7 +7915,6 @@
     showBar('generating');
     startScrollTracking();
     saveSession();
-    sendCheckpoint('generate_started');
     writeScrollY(window.scrollY);
     if (variantObserver) variantObserver.disconnect();
     variantObserver = startVariantObserver(currentSessionId);
@@ -8238,7 +8236,8 @@
     // rasterization from delaying the fetch itself.
     if (!hasAnnotations) {
       basePayload.clientSentAt = Date.now();
-      await sendEvent(basePayload);
+      const created = await sendEvent(basePayload);
+      if (created?.ok && currentSessionId === basePayload.id) sendCheckpoint('generate_started');
     }
 
     let screenshotPath;
@@ -8279,7 +8278,10 @@
     // is semantic input. Plain requests were already dispatched above.
     if (hasAnnotations) {
       basePayload.clientSentAt = Date.now();
-      sendEvent(screenshotPath ? { ...basePayload, screenshotPath } : basePayload);
+      const created = await sendEvent(screenshotPath ? { ...basePayload, screenshotPath } : basePayload);
+      // Capture/upload can take seconds. Progress before this acknowledgment
+      // refers to an unknown session and would clear our own active work.
+      if (created?.ok && currentSessionId === basePayload.id) sendCheckpoint('generate_started');
     }
   }
 
diff --git a/tests/framework-fixtures/vite8-sveltekit-stateful/fixture.json b/tests/framework-fixtures/vite8-sveltekit-stateful/fixture.json
index 945c90668..a2f8fa6ba 100644
--- a/tests/framework-fixtures/vite8-sveltekit-stateful/fixture.json
+++ b/tests/framework-fixtures/vite8-sveltekit-stateful/fixture.json
@@ -57,6 +57,12 @@
     "readyPattern": "Local:\\s+https?://[^:]+:(\\d+)",
     "readyTimeoutMs": 120000,
     "steer": false,
+    "liveChrome": {
+      "annotations": {
+        "selector": "h1.hero-title",
+        "uploadDelayMs": 300
+      }
+    },
     "pickSelector": "ul.expense-list",
     "pickPosition": {
       "x": 10,
diff --git a/tests/live-browser-source.test.mjs b/tests/live-browser-source.test.mjs
index 1148a5542..6f4f440c6 100644
--- a/tests/live-browser-source.test.mjs
+++ b/tests/live-browser-source.test.mjs
@@ -2,12 +2,53 @@ import { describe, it } from 'node:test';
 import assert from 'node:assert/strict';
 import { readFileSync } from 'node:fs';
 import { join } from 'node:path';
+import { runInNewContext } from 'node:vm';
 
 const SOURCE = readFileSync(join(process.cwd(), 'skill/scripts/live-browser.js'), 'utf-8');
 const PENDING_DOCK_POSITION_SOURCE = SOURCE.match(/function positionPendingDock\(\) \{[\s\S]*?\n  \}/)?.[0] || '';
 const CAPTURE_AND_EMIT_SOURCE = SOURCE.match(/async function captureAndEmit\([\s\S]*?\n  \}/)?.[0] || '';
 
 describe('live-browser source contracts', () => {
+  it('does not checkpoint a generation before captureAndEmit creates its session', () => {
+    for (const name of ['handleGo', 'handleInsertCreate']) {
+      const body = SOURCE.match(new RegExp(`function ${name}\\(\\) \\{[\\s\\S]*?\\n  \\}`))?.[0];
+      assert.ok(body);
+      assert.doesNotMatch(body, /sendCheckpoint\('generate_started'\)/);
+    }
+  });
+
+  for (const annotated of [false, true]) {
+    for (const outcome of ['created', 'failed', 'superseded']) {
+      it(`${annotated ? 'annotated' : 'plain'} generation checkpoints only its acknowledged current session (${outcome})`, async () => {
+        const capture = Promise.withResolvers();
+        const creation = Promise.withResolvers();
+        const events = [];
+        const context = {
+          currentSessionId: 'session-a', state: 'GENERATING', PORT: 1234, TOKEN: 'test',
+          console, Date,
+          captureElementToBlob: () => capture.promise,
+          showShaderOverlay() {},
+          fetch: async () => ({ ok: true, json: async () => ({ path: '/annotation.png' }) }),
+          sendEvent: async (payload) => { events.push(payload.type); return creation.promise; },
+          sendCheckpoint: (reason) => events.push(reason),
+        };
+        const emit = runInNewContext(`(${CAPTURE_AND_EMIT_SOURCE})`, context);
+        const pending = emit({}, { type: 'generate', id: 'session-a' }, {
+          comments: annotated ? [{ text: 'change title' }] : [], strokes: [],
+        }, {});
+        await new Promise(resolve => setImmediate(resolve));
+        assert.deepEqual(events, annotated ? [] : ['generate']);
+        capture.resolve({ blob: {}, paper: 'white' });
+        await new Promise(resolve => setImmediate(resolve));
+        assert.deepEqual(events, ['generate'], 'capture/upload must not checkpoint before creation is acknowledged');
+        if (outcome === 'superseded') context.currentSessionId = 'session-b';
+        creation.resolve(outcome === 'failed' ? null : { ok: true });
+        await pending;
+        assert.deepEqual(events, outcome === 'created' ? ['generate', 'generate_started'] : ['generate']);
+      });
+    }
+  }
+
   it('reports foreground poll connectivity without a background worker dependency', () => {
     assert.match(
       SOURCE,
@@ -29,7 +70,7 @@ describe('live-browser source contracts', () => {
     );
     assert.match(
       CAPTURE_AND_EMIT_SOURCE,
-      /if \(hasAnnotations\) \{[\s\S]*?basePayload\.clientSentAt = Date\.now\(\);\s*sendEvent\(screenshotPath \? \{ \.\.\.basePayload, screenshotPath \} : basePayload\);\s*\}/,
+      /if \(hasAnnotations\) \{[\s\S]*?basePayload\.clientSentAt = Date\.now\(\);\s*const created = await sendEvent\(screenshotPath \? \{ \.\.\.basePayload, screenshotPath \} : basePayload\);/,
       'annotated generation should dispatch exactly after capture and upload resolve',
     );
   });
diff --git a/tests/live-e2e.test.mjs b/tests/live-e2e.test.mjs
index e03d5cf85..f4224c4b7 100644
--- a/tests/live-e2e.test.mjs
+++ b/tests/live-e2e.test.mjs
@@ -1283,17 +1283,21 @@ for (const { name, fixture } of fixtures) {
         const pickSelector = annotation.selector || fixture.runtime.pickSelector || 'h1.hero-title';
         try {
           await waitForHandshake(page);
+          if (annotation.uploadDelayMs) {
+            await page.route('**/annotation?*', async (route) => {
+              await new Promise(resolve => setTimeout(resolve, annotation.uploadDelayMs));
+              await route.continue();
+            });
+          }
           if (fixture.runtime.preActions) await runPreActions(page, fixture.runtime.preActions);
           await pickElement(page, pickSelector, { resetPickMode: true });
           await drawAnnotationPinAndStroke(page, {
             comment: annotation.comment || 'Make this selected element easier to scan',
           });
           await clickGo(page);
-          await waitForCyclingRobust(page, 3, {
-            agentMode,
-            preActions: fixture.runtime.preActions,
-            log: (m) => t.diagnostic(m),
-          });
+          // A reload would mask a checkpoint-before-creation race by adopting
+          // the session again. Annotated generation must complete in this tab.
+          await waitForCycling(page, 3, { timeout: agentMode === 'llm' ? 180_000 : 30_000 });
 
           const generateEvent = recordedGenerateEvents.at(-1);
           await assertAnnotationUploadEvent(generateEvent);
@@ -1302,7 +1306,7 @@ for (const { name, fixture } of fixtures) {
 
           const sourceFile = await locateSessionFile(session.appRoot);
           const svelteComponentTarget = svelteComponentTargetFor(sourceFile);
-          await clickNext(page);
+          await cycleToVariant(page, 2, 3);
           assert.equal(await getVisibleVariant(page), 2, 'variant 2 visible after annotated generate');
           await clickAccept(page, { expectedVariant: 2 });
           await waitForBarHidden(page);
diff --git a/tests/live-svelte-adapter-deepseek.test.mjs b/tests/live-svelte-adapter-deepseek.test.mjs
index af77c8c49..7ec030a17 100644
--- a/tests/live-svelte-adapter-deepseek.test.mjs
+++ b/tests/live-svelte-adapter-deepseek.test.mjs
@@ -26,7 +26,6 @@ import {
   clickEditCopy,
   clickExitLiveMode,
   clickGo,
-  clickNext,
   cycleToVariant,
   clickSaveEdit,
   drawAnnotationPinAndStroke,
@@ -282,7 +281,7 @@ async function runAnnotationGenerateFlow({ page, tmp, evidence }) {
   const generateEvent = latestJournalEvent(tmp, (event) => event.type === 'generate' && event.screenshotPath);
   await assertAnnotationUploadEvent(generateEvent);
   assert.ok(existsSync(generateEvent.screenshotPath), 'annotation screenshot file exists');
-  await clickNext(page);
+  await cycleTo(page, 2);
   await assertVariantCounter(page, 2, 3);
   await evidence.capture('annotation-cycle');
   await clickDiscard(page);