diff --git a/src/services/chat/matrix/token-extractor.ts b/src/services/chat/matrix/token-extractor.ts
index ad16bec..ac60ce4 100644
--- a/src/services/chat/matrix/token-extractor.ts
+++ b/src/services/chat/matrix/token-extractor.ts
@@ -102,11 +102,27 @@ export async function extractMatrixCredentials(
 
     page.on('request', onRequest);
 
-    logger.info('[matrix] loading chat.reddit.com to capture access token...');
-    await page.goto('https://chat.reddit.com/', {
-      waitUntil: 'domcontentloaded',
-      timeout: 30_000,
-    });
+    // Reddit now redirects `chat.reddit.com` → `www.reddit.com/chat/`. Going
+    // direct to the canonical URL avoids one redirect hop and means the
+    // session cookie the bot already has for www.reddit.com is applied to
+    // the very first request, rather than only after a cross-subdomain
+    // bounce that's been bouncing logged-in sessions to the login wall.
+    //
+    // We start the navigation but don't await it — the request listener
+    // resolves credsPromise the moment the SPA fires off its first authed
+    // call to matrix.redditspace.com, which may happen well before the page
+    // reaches `networkidle`. Awaiting goto would block past that point.
+    logger.info('[matrix] loading www.reddit.com/chat/ to capture access token...');
+    void page
+      .goto('https://www.reddit.com/chat/', {
+        waitUntil: 'domcontentloaded',
+        timeout: timeoutMs,
+      })
+      .catch((err) => {
+        logger.warn(
+          `[matrix] page.goto error (ignored, still listening): ${err instanceof Error ? err.message : String(err)}`,
+        );
+      });
 
     const timeout = new Promise<MatrixCredentials>((_, reject) =>
       setTimeout(
diff --git a/src/web/routes/debug.ts b/src/web/routes/debug.ts
index 2fd9fcf..2837d46 100644
--- a/src/web/routes/debug.ts
+++ b/src/web/routes/debug.ts
@@ -21,6 +21,45 @@ export function createDebugRouter(ctx: WebContext): Router {
     res.sendFile(p);
   });
 
+  // Dumps the browser context's cookies (names + metadata only — values are
+  // hashed) so we can tell which session/OAuth cookies are set after the
+  // auto-login and which the chat surface might be missing.
+  router.get('/debug/cookies', async (req, res) => {
+    const browser = ctx.services.browser;
+    if (!browser) {
+      res.status(500).json({ error: 'Browser client not initialized' });
+      return;
+    }
+    const context = browser.getContext();
+    if (!context) {
+      res.status(500).json({ error: 'Browser context not available' });
+      return;
+    }
+    try {
+      const reveal = req.query.reveal === '1';
+      const urls = ['https://www.reddit.com', 'https://chat.reddit.com', 'https://matrix.redditspace.com'];
+      const out: Record<string, unknown> = {};
+      for (const u of urls) {
+        const cookies = await context.cookies(u);
+        out[u] = cookies.map((c) => ({
+          name: c.name,
+          domain: c.domain,
+          path: c.path,
+          httpOnly: c.httpOnly,
+          secure: c.secure,
+          sameSite: c.sameSite,
+          expires: c.expires,
+          valueLen: c.value.length,
+          value: reveal ? c.value : undefined,
+        }));
+      }
+      res.json(out);
+    } catch (error) {
+      ctx.logger.error('Cookie dump failed:', error);
+      res.status(500).json({ error: String(error) });
+    }
+  });
+
   router.post('/debug/inspect-dom', async (req, res) => {
     if (!ctx.services.chat) {
       res.status(500).json({ error: 'Chat service not initialized' });