diff --git a/packages/web/bin/cli.js b/packages/web/bin/cli.js
index 82517971..d52d5495 100755
--- a/packages/web/bin/cli.js
+++ b/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;
@@ -3006,30 +3007,43 @@ const commands = {
     child.unref();
     serveSpin?.start(`Starting OpenChamber on port ${targetPort === 0 ? 'auto' : targetPort}...`);
 
-    const resolvedPort = await new Promise((resolve) => {
-      let settled = false;
-      const timeout = setTimeout(() => {
-        if (settled) return;
-        settled = true;
-        resolve(targetPort);
-      }, 5000);
+    let resolvedPort;
+    try {
+      resolvedPort = await new Promise((resolve, reject) => {
+        let settled = false;
+        const timeout = setTimeout(() => {
+          if (settled) return;
+          settled = true;
+          reject(new Error(`OpenChamber daemon did not report ready within ${DAEMON_READY_TIMEOUT_MS / 1000}s`));
+        }, DAEMON_READY_TIMEOUT_MS);
 
-      child.on('message', (msg) => {
-        if (settled) return;
-        if (msg && msg.type === 'openchamber:ready' && typeof msg.port === 'number') {
+        child.on('message', (msg) => {
+          if (settled) return;
+          if (msg && msg.type === 'openchamber:ready' && typeof msg.port === 'number') {
+            settled = true;
+            clearTimeout(timeout);
+            resolve(msg.port);
+          }
+        });
+
+        child.on('error', (error) => {
+          if (settled) return;
           settled = true;
           clearTimeout(timeout);
-          resolve(msg.port);
-        }
-      });
+          reject(error);
+        });
 
-      child.on('exit', () => {
-        if (settled) return;
-        settled = true;
-        clearTimeout(timeout);
-        resolve(targetPort);
+        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) {
diff --git a/packages/web/server/lib/opencode/server-startup-runtime.js b/packages/web/server/lib/opencode/server-startup-runtime.js
index ddcc4700..551badd5 100644
--- a/packages/web/server/lib/opencode/server-startup-runtime.js
+++ b/packages/web/server/lib/opencode/server-startup-runtime.js
@@ -38,68 +38,86 @@ export const createServerStartupRuntime = (dependencies) => {
       server.once('error', onError);
       const onListening = async () => {
         server.off('error', onError);
-        const addressInfo = server.address();
-        activePort = typeof addressInfo === 'object' && addressInfo ? addressInfo.port : port;
-
         try {
-          process.send?.({ type: 'openchamber:ready', port: activePort });
-        } catch {
-          // ignore
-        }
+          const addressInfo = server.address();
+          activePort = typeof addressInfo === 'object' && addressInfo ? addressInfo.port : port;
 
-        const displayHost = (bindHost === '0.0.0.0' || bindHost === '::' || bindHost === '[::]')
-          ? 'localhost'
-          : (bindHost.includes(':') ? `[${bindHost}]` : bindHost);
-        console.log(`OpenChamber server listening on ${bindHost}:${activePort}`);
-        console.log(`Health check: http://${displayHost}:${activePort}/health`);
-        console.log(`Web interface: http://${displayHost}:${activePort}`);
-
-        if (startupTunnelRequest) {
-          const startupModeLabel = startupTunnelRequest.mode === TUNNEL_MODE_QUICK
-            ? 'Quick Tunnel'
-            : (startupTunnelRequest.mode === TUNNEL_MODE_MANAGED_LOCAL
-              ? 'Managed Local Tunnel'
-              : (startupTunnelRequest.mode === TUNNEL_MODE_MANAGED_REMOTE ? 'Managed Remote Tunnel' : 'Tunnel'));
-          console.log(`\nInitializing ${startupModeLabel} for provider '${startupTunnelRequest.provider}'...`);
-          try {
-            const { publicUrl, mode } = await startTunnelWithNormalizedRequest({
-              provider: startupTunnelRequest.provider,
-              mode: startupTunnelRequest.mode,
-              intent: startupTunnelRequest.intent,
-              hostname: startupTunnelRequest.hostname,
-              token: startupTunnelRequest.token,
-              configPath: startupTunnelRequest.configPath,
-              selectedPresetId: '',
-              selectedPresetName: '',
-            });
-            if (publicUrl) {
-              tunnelAuthController.setActiveTunnel({
-                tunnelId: crypto.randomUUID(),
-                publicUrl,
-                mode,
-              });
-              const settings = await readSettingsFromDiskMigrated();
-              const bootstrapTtlMs = settings?.tunnelBootstrapTtlMs === null
-                ? null
-                : normalizeTunnelBootstrapTtlMs(settings?.tunnelBootstrapTtlMs);
-              const bootstrapToken = tunnelAuthController.issueBootstrapToken({ ttlMs: bootstrapTtlMs });
-              const connectUrl = `${publicUrl.replace(/\/$/, '')}/connect?t=${encodeURIComponent(bootstrapToken.token)}`;
-              if (onTunnelReady) {
-                onTunnelReady(publicUrl, connectUrl);
-              } else {
-                console.log(`\n🌐 Tunnel URL: ${connectUrl}`);
-                console.log('🔑 One-time connect link (expires after first use)\n');
-              }
-            } else if (onTunnelReady) {
-              onTunnelReady(publicUrl, null);
+          if (typeof process.send === 'function') {
+            if (!process.connected) {
+              throw new Error('OpenChamber startup IPC channel disconnected before ready notification');
             }
-          } catch (error) {
-            console.error(`Failed to start tunnel: ${error.message}`);
-            console.log('Continuing without tunnel...');
-          }
-        }
 
-        resolve();
+            await new Promise((resolveReadyNotification, rejectReadyNotification) => {
+              try {
+                process.send({ type: 'openchamber:ready', port: activePort }, (error) => {
+                  if (error) {
+                    rejectReadyNotification(error);
+                    return;
+                  }
+                  resolveReadyNotification();
+                });
+              } catch (error) {
+                rejectReadyNotification(error);
+              }
+            });
+          }
+
+          const displayHost = (bindHost === '0.0.0.0' || bindHost === '::' || bindHost === '[::]')
+            ? 'localhost'
+            : (bindHost.includes(':') ? `[${bindHost}]` : bindHost);
+          console.log(`OpenChamber server listening on ${bindHost}:${activePort}`);
+          console.log(`Health check: http://${displayHost}:${activePort}/health`);
+          console.log(`Web interface: http://${displayHost}:${activePort}`);
+
+          if (startupTunnelRequest) {
+            const startupModeLabel = startupTunnelRequest.mode === TUNNEL_MODE_QUICK
+              ? 'Quick Tunnel'
+              : (startupTunnelRequest.mode === TUNNEL_MODE_MANAGED_LOCAL
+                ? 'Managed Local Tunnel'
+                : (startupTunnelRequest.mode === TUNNEL_MODE_MANAGED_REMOTE ? 'Managed Remote Tunnel' : 'Tunnel'));
+            console.log(`\nInitializing ${startupModeLabel} for provider '${startupTunnelRequest.provider}'...`);
+            try {
+              const { publicUrl, mode } = await startTunnelWithNormalizedRequest({
+                provider: startupTunnelRequest.provider,
+                mode: startupTunnelRequest.mode,
+                intent: startupTunnelRequest.intent,
+                hostname: startupTunnelRequest.hostname,
+                token: startupTunnelRequest.token,
+                configPath: startupTunnelRequest.configPath,
+                selectedPresetId: '',
+                selectedPresetName: '',
+              });
+              if (publicUrl) {
+                tunnelAuthController.setActiveTunnel({
+                  tunnelId: crypto.randomUUID(),
+                  publicUrl,
+                  mode,
+                });
+                const settings = await readSettingsFromDiskMigrated();
+                const bootstrapTtlMs = settings?.tunnelBootstrapTtlMs === null
+                  ? null
+                  : normalizeTunnelBootstrapTtlMs(settings?.tunnelBootstrapTtlMs);
+                const bootstrapToken = tunnelAuthController.issueBootstrapToken({ ttlMs: bootstrapTtlMs });
+                const connectUrl = `${publicUrl.replace(/\/$/, '')}/connect?t=${encodeURIComponent(bootstrapToken.token)}`;
+                if (onTunnelReady) {
+                  onTunnelReady(publicUrl, connectUrl);
+                } else {
+                  console.log(`\n🌐 Tunnel URL: ${connectUrl}`);
+                  console.log('🔑 One-time connect link (expires after first use)\n');
+                }
+              } else if (onTunnelReady) {
+                onTunnelReady(publicUrl, null);
+              }
+            } catch (error) {
+              console.error(`Failed to start tunnel: ${error.message}`);
+              console.log('Continuing without tunnel...');
+            }
+          }
+
+          resolve();
+        } catch (error) {
+          reject(error);
+        }
       };
 
       server.listen(port, bindHost, onListening);