fix: make daemon startup ready handoff reliable

Wait longer for slow daemon startup
Fail cleanly when ready handoff does not complete
Avoid orphaned daemon processes after startup timeout

packages/web/bin/cli.js

@@ -29,6 +29,7 @@ const __dirname = path.dirname(__filename);
 
 const DEFAULT_PORT = 3000;
 const DEFAULT_TAIL_LINES = 200;
+const DAEMON_READY_TIMEOUT_MS = 30000;
 const LOG_ROTATE_MAX_BYTES = 10 * 1024 * 1024;
 const LOG_ROTATE_KEEP = 5;
 const TUNNEL_PROFILES_VERSION = 1;
@@ -3006,13 +3007,15 @@ const commands = {
     child.unref();
     serveSpin?.start(`Starting OpenChamber on port ${targetPort === 0 ? 'auto' : targetPort}...`);
 
-    const resolvedPort = await new Promise((resolve) => {
+    let resolvedPort;
+    try {
+      resolvedPort = await new Promise((resolve, reject) => {
         let settled = false;
         const timeout = setTimeout(() => {
           if (settled) return;
           settled = true;
-        resolve(targetPort);
+          reject(new Error(`OpenChamber daemon did not report ready within ${DAEMON_READY_TIMEOUT_MS / 1000}s`));
-      }, 5000);
+        }, DAEMON_READY_TIMEOUT_MS);
 
         child.on('message', (msg) => {
           if (settled) return;
@@ -3023,13 +3026,24 @@ const commands = {
           }
         });
 
-      child.on('exit', () => {
+        child.on('error', (error) => {
           if (settled) return;
           settled = true;
           clearTimeout(timeout);
-        resolve(targetPort);
+          reject(error);
+        });
+
+        child.on('exit', (code, signal) => {
+          if (settled) return;
+          settled = true;
+          clearTimeout(timeout);
+          reject(new Error(`OpenChamber daemon exited before reporting ready${signal ? ` (${signal})` : ` (code ${code ?? 'unknown'})`}`));
         });
       });
+    } catch (error) {
+      await terminateProcessTree(child.pid, { gracefulTimeoutMs: 1500, forceTimeoutMs: 1500 });
+      throw error;
+    }
 
     try {
       if (typeof child.disconnect === 'function' && child.connected) {

packages/web/server/lib/opencode/server-startup-runtime.js

@@ -38,13 +38,28 @@ export const createServerStartupRuntime = (dependencies) => {
       server.once('error', onError);
       const onListening = async () => {
         server.off('error', onError);
+        try {
           const addressInfo = server.address();
           activePort = typeof addressInfo === 'object' && addressInfo ? addressInfo.port : port;
 
+          if (typeof process.send === 'function') {
+            if (!process.connected) {
+              throw new Error('OpenChamber startup IPC channel disconnected before ready notification');
+            }
+
+            await new Promise((resolveReadyNotification, rejectReadyNotification) => {
               try {
-          process.send?.({ type: 'openchamber:ready', port: activePort });
+                process.send({ type: 'openchamber:ready', port: activePort }, (error) => {
-        } catch {
+                  if (error) {
-          // ignore
+                    rejectReadyNotification(error);
+                    return;
+                  }
+                  resolveReadyNotification();
+                });
+              } catch (error) {
+                rejectReadyNotification(error);
+              }
+            });
           }
 
           const displayHost = (bindHost === '0.0.0.0' || bindHost === '::' || bindHost === '[::]')
@@ -100,6 +115,9 @@ export const createServerStartupRuntime = (dependencies) => {
           }
 
           resolve();
+        } catch (error) {
+          reject(error);
+        }
       };
 
       server.listen(port, bindHost, onListening);