diff --git a/src/cli/program.ts b/src/cli/program.ts
index bdb1efc67..63b0f629a 100644
--- a/src/cli/program.ts
+++ b/src/cli/program.ts
@@ -14,7 +14,9 @@ import { defaultRuntime } from "../runtime.js";
 import { VERSION } from "../version.js";
 import { startWebChatServer } from "../webchat/server.js";
 import { createDefaultDeps } from "./deps.js";
-import { forceFreePort, listPortListeners } from "./ports.js";
+import { forceFreePort, listPortListeners, parseLsofOutput } from "./ports.js";
+
+export { forceFreePort, listPortListeners, parseLsofOutput };
 
 export function buildProgram() {
   const program = new Command();
@@ -489,7 +491,7 @@ Examples:
     .option(
       "--probe",
       "Also attempt a live Baileys connect (can conflict if gateway is already connected)",
-      false,
+      true,
     )
     .action(async (opts) => {
       setVerbose(Boolean(opts.verbose));
@@ -508,7 +510,7 @@ Examples:
           {
             json: Boolean(opts.json),
             timeoutMs: timeout,
-            probe: Boolean(opts.probe),
+            probe: opts.probe ?? true,
           },
           defaultRuntime,
         );
@@ -564,6 +566,19 @@ Shows token usage per session when the agent reports it; set inbound.reply.agent
         ? Number.parseInt(String(opts.port), 10)
         : undefined;
       const server = await startWebChatServer(port);
+      if (!server) {
+        const targetPort = port ?? 18788;
+        const msg = `webchat failed to start on http://127.0.0.1:${targetPort}/`;
+        if (opts.json) {
+          defaultRuntime.error(
+            JSON.stringify({ error: msg, port: targetPort }),
+          );
+        } else {
+          defaultRuntime.error(danger(msg));
+        }
+        defaultRuntime.exit(1);
+        return;
+      }
       const payload = {
         port: server.port,
         basePath: "/",
diff --git a/src/commands/health.ts b/src/commands/health.ts
index f1655385b..e3a5d9cce 100644
--- a/src/commands/health.ts
+++ b/src/commands/health.ts
@@ -76,7 +76,7 @@ async function probeWebConnect(timeoutMs: number): Promise<HealthConnect> {
     const status = getStatusCode(err);
     // Conflict/duplicate sessions are expected when the primary gateway session
     // is already connected. Treat these as healthy so health checks don’t flap.
-    if (status === 409 || status === 440 || status === 515) {
+    if (status === 409 || status === 515) {
       return {
         ok: true,
         status,
@@ -239,8 +239,9 @@ export async function healthCommand(
   opts: { json?: boolean; timeoutMs?: number; probe?: boolean },
   runtime: RuntimeEnv,
 ) {
+  const probe = opts.probe ?? true;
   const summary = await getHealthSnapshot(opts.timeoutMs, {
-    probe: opts.probe,
+    probe,
   });
   const fatal =
     !summary.web.linked ||
diff --git a/src/gateway/server.ts b/src/gateway/server.ts
index b1938b09a..76d60e398 100644
--- a/src/gateway/server.ts
+++ b/src/gateway/server.ts
@@ -97,7 +97,7 @@ function buildSnapshot(): Snapshot {
 
 const MAX_PAYLOAD_BYTES = 512 * 1024; // cap incoming frame size
 const MAX_BUFFERED_BYTES = 1.5 * 1024 * 1024; // per-connection send buffer limit
-const HANDSHAKE_TIMEOUT_MS = 10_000;
+const HANDSHAKE_TIMEOUT_MS = 3_000;
 const TICK_INTERVAL_MS = 30_000;
 const HEALTH_REFRESH_INTERVAL_MS = 60_000;
 const DEDUPE_TTL_MS = 5 * 60_000;
@@ -754,9 +754,11 @@ export async function startGatewayServer(port = 18789): Promise<GatewayServer> {
                   typeof a?.content === "string"
                     ? a.content
                     : ArrayBuffer.isView(a?.content)
-                      ? Buffer.from(a.content as ArrayBufferLike).toString(
-                          "base64",
-                        )
+                      ? Buffer.from(
+                          a.content.buffer,
+                          a.content.byteOffset,
+                          a.content.byteLength,
+                        ).toString("base64")
                       : undefined,
               })) ?? [];
             let messageWithAttachments = p.message;
@@ -1076,9 +1078,7 @@ export async function startGatewayServer(port = 18789): Promise<GatewayServer> {
   defaultRuntime.log(`gateway log file: ${getResolvedLoggerSettings().file}`);
 
   // Start loopback WebChat server (unless disabled via config).
-  void ensureWebChatServerFromConfig({
-    gatewayUrl: `ws://127.0.0.1:${port}`,
-  })
+  void ensureWebChatServerFromConfig()
     .then((webchat) => {
       if (webchat) {
         defaultRuntime.log(