diff --git a/.github/extensions/ai-engineer-coach/README.md b/.github/extensions/ai-engineer-coach/README.md
index 1f849a8f..8cf26517 100644
--- a/.github/extensions/ai-engineer-coach/README.md
+++ b/.github/extensions/ai-engineer-coach/README.md
@@ -37,6 +37,6 @@ Open with `{ "page": "curiosity" }` to start on the Curiosity page. Omit input t
 
 - `extension.mjs` owns build detection and a single `127.0.0.1` HTTP server, and declares the canvas via `createCanvas` / `joinSession`.
 - `dist/canvas-host.cjs` (built from `src/canvas/host.ts`) provides the request handler: the dashboard shell, the asset routes, an SSE channel for parse progress, and the `/rpc` endpoint.
-- The dashboard talks to the host through an injected `acquireVsCodeApi` shim, so the webview code is unchanged between VS Code and canvas.
+- The dashboard talks to the host through an injected `acquireVsCodeApi` shim, so the webview code is unchanged between VS Code and canvas. The shim opens the SSE stream only after the dashboard posts `ready` (the same handshake the VS Code panel uses), so the progress and `dataReady` events replayed on connect always reach a listener.
 
 The harness breakdown distinguishes **GitHub Copilot App** (desktop) from **GitHub Copilot CLI** (terminal) using the `remoteSteerable` marker present in app session logs.
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 19be66f0..95d5ea54 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+- Fix canvas mode intermittently loading with an empty content pane or a stuck
+  loading screen (#269): the canvas bridge now subscribes to host events only
+  after the dashboard signals it is listening, so the replayed `dataReady` is
+  never dropped
 - Fix Coding Moments image counting and loading across VS Code, Copilot CLI/App,
   Claude (including subagents), Codex, OpenCode JSON/SQLite, and Xcode (#292);
   extract images off-thread with bounded local reads and session-scoped caching
diff --git a/src/canvas/bridge-shim.test.ts b/src/canvas/bridge-shim.test.ts
new file mode 100644
index 00000000..8f5524db
--- /dev/null
+++ b/src/canvas/bridge-shim.test.ts
@@ -0,0 +1,59 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See LICENSE in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+/**
+ * @vitest-environment jsdom
+ *
+ * Regression test for #269. The canvas host replays `dataReady` on /events the moment a client
+ * connects. If the bridge shim subscribes before app.js has attached its message listener (at
+ * shim evaluation, or on DOMContentLoaded when the bundle has not run yet), the replay reaches
+ * no listener and the dashboard never leaves its loading screen. This wires the shim the host
+ * actually serves to the real webview listener and replays as soon as the stream opens.
+ */
+
+import { IncomingMessage, ServerResponse } from 'http';
+import { Socket } from 'net';
+import { runInThisContext } from 'vm';
+import { afterEach, expect, it, vi } from 'vitest';
+import { createCanvasHost } from './host';
+
+afterEach(() => vi.unstubAllGlobals());
+
+function servedBridgeShim(): string {
+  const host = createCanvasHost({ distDir: '/fixture/dist' });
+  const req = new IncomingMessage(new Socket());
+  req.url = '/';
+  req.method = 'GET';
+  const res = new ServerResponse(req);
+  const end = vi.spyOn(res, 'end').mockImplementation(() => res);
+  host.handle(req, res);
+  host.dispose();
+  const html = String(end.mock.calls[0][0]);
+  const start = html.indexOf('<script>') + '<script>'.length;
+  return html.slice(start, html.indexOf('</script>', start));
+}
+
+it('delivers the replayed dataReady even when the page finishes loading before the dashboard listens', async () => {
+  const streams: string[] = [];
+  vi.stubGlobal('EventSource', class {
+    onmessage?: (event: { data: string }) => void;
+    constructor(url: string) {
+      streams.push(url);
+      setTimeout(() => this.onmessage?.({ data: JSON.stringify({ type: 'dataReady', currentWorkspace: 'my-repo' }) }));
+    }
+  });
+  runInThisContext(servedBridgeShim());
+
+  // An async or code-split bundle can attach its listener after DOMContentLoaded has fired.
+  document.dispatchEvent(new Event('DOMContentLoaded'));
+  await new Promise(resolve => setTimeout(resolve, 10));
+
+  const { initMessageListener } = await import('../webview/shared');
+  const onDataReady = vi.fn();
+  initMessageListener(() => { /* progress is not under test */ }, onDataReady);
+
+  await vi.waitFor(() => expect(onDataReady).toHaveBeenCalledWith('my-repo', { skippedFiles: 0, skippedLines: 0 }));
+  expect(streams).toEqual(['/events']);
+});
diff --git a/src/canvas/host.test.ts b/src/canvas/host.test.ts
index c3733e40..0190f799 100644
--- a/src/canvas/host.test.ts
+++ b/src/canvas/host.test.ts
@@ -105,7 +105,7 @@ it('retains startup errors for RPC calls and clients that connect later', async
   host.dispose();
 });
 
-it.each(['script', 'SCRIPT', 'Script'])('waits for app.js to load before subscribing to replayed dataReady events (%s tags)', (scriptTag) => {
+it.each(['script', 'SCRIPT', 'Script'])('subscribes to replayed dataReady events only after the webview announces it is listening (%s tags)', (scriptTag) => {
   const host = createCanvasHost({ distDir: '/fixture/dist' });
   const html = String(request(host, '/').end.mock.calls[0][0])
     .replaceAll('<script>', `<${scriptTag}>`)
@@ -113,19 +113,26 @@ it.each(['script', 'SCRIPT', 'Script'])('waits for app.js to load before subscri
   const script = /<script>([\s\S]*?)<\/script>/i.exec(html)![1];
   const listeners = new Map<string, () => void>();
   const dispatchEvent = vi.fn();
-  const streams: { onmessage?: (event: { data: string }) => void }[] = [];
+  const streams: { url: string; onmessage?: (event: { data: string }) => void }[] = [];
+  const sandboxWindow: { dispatchEvent: typeof dispatchEvent; acquireVsCodeApi?: () => { postMessage(msg: unknown): void } } = { dispatchEvent };
   runInNewContext(script, {
-    window: { dispatchEvent },
+    window: sandboxWindow,
     document: { addEventListener: (name: string, callback: () => void) => listeners.set(name, callback) },
     MessageEvent,
     EventSource: class {
       onmessage?: (event: { data: string }) => void;
-      constructor() { streams.push(this); }
+      constructor(readonly url: string) { streams.push(this); }
     },
   });
+  // Page lifecycle events are no readiness signal: the bundle may not be listening yet (#269).
+  for (const callback of listeners.values()) callback();
+  const api = sandboxWindow.acquireVsCodeApi!();
+  api.postMessage({ type: 'progress' });
   expect(streams).toHaveLength(0);
-  listeners.get('DOMContentLoaded')!();
+  api.postMessage({ type: 'ready' });
+  api.postMessage({ type: 'ready' });
   expect(streams).toHaveLength(1);
+  expect(streams[0].url).toBe('/events');
   streams[0].onmessage!({ data: '{"type":"dataReady"}' });
   expect(dispatchEvent).toHaveBeenCalledWith(expect.objectContaining({ data: { type: 'dataReady' } }));
   host.dispose();
diff --git a/src/canvas/host.ts b/src/canvas/host.ts
index 2d2e5b37..7e388446 100644
--- a/src/canvas/host.ts
+++ b/src/canvas/host.ts
@@ -310,12 +310,23 @@ html,body{height:100%;margin:0;background:var(--vscode-editor-background);color:
 /* Stands in for the VS Code webview bridge. `acquireVsCodeApi` must exist before
  * app.js runs. RPC requests become POSTs to /rpc; responses, progress, and
  * dataReady arrive via SSE and are re-dispatched as window message events so the
- * unchanged webview message listener handles them. */
+ * unchanged webview message listener handles them. /events replays the latest
+ * progress and dataReady on connect, so the stream opens only once the webview
+ * posts `ready` (sent after its message listener is attached), the same handshake
+ * the VS Code panel uses. Subscribing earlier can drop that replay before app.js
+ * listens, leaving the dashboard stuck on its loading screen (#269). */
 const BRIDGE_SHIM = `(function(){
 var STATE_KEY='ai-engineer-coach-canvas-state';
+var events=null;
 function dispatch(data){window.dispatchEvent(new MessageEvent('message',{data:data}));}
+function subscribe(){
+if(events)return;
+events=new EventSource('/events');
+events.onmessage=function(e){try{dispatch(JSON.parse(e.data));}catch(err){}};
+}
 var api={
 postMessage:function(msg){
+if(msg&&msg.type==='ready'){subscribe();return;}
 if(!msg||msg.type!=='request')return;
 if(msg.method==='openExternal'){
 var url=msg.params&&msg.params.url;
@@ -339,8 +350,4 @@ getState:function(){try{return JSON.parse(localStorage.getItem(STATE_KEY)||'null
 setState:function(s){try{localStorage.setItem(STATE_KEY,JSON.stringify(s));}catch(e){}return s;}
 };
 window.acquireVsCodeApi=function(){return api;};
-document.addEventListener('DOMContentLoaded',function(){
-var es=new EventSource('/events');
-es.onmessage=function(e){try{dispatch(JSON.parse(e.data));}catch(err){}};
-},{once:true});
 })();`;