diff --git a/packages/cli/src/lib/web-dir.ts b/packages/cli/src/lib/web-dir.ts
index bb3fb5193..c67c0a381 100644
--- a/packages/cli/src/lib/web-dir.ts
+++ b/packages/cli/src/lib/web-dir.ts
@@ -10,6 +10,7 @@ import { createRequire } from "node:module";
 import { fileURLToPath } from "node:url";
 import { resolve, dirname } from "node:path";
 import { existsSync } from "node:fs";
+import { isLinux, isWindows } from "@aoagents/ao-core";
 import { formatCommandError } from "./cli-errors.js";
 
 const __filename = fileURLToPath(import.meta.url);
@@ -32,9 +33,18 @@ export function isPortAvailable(port: number): Promise<boolean> {
   return new Promise((resolve) => {
     const s = new Socket();
     s.setTimeout(300);
-    s.once("connect", () => { s.destroy(); resolve(false); }); // something listening → in use
-    s.once("error", () => { s.destroy(); resolve(true); });    // ECONNREFUSED → free
-    s.once("timeout", () => { s.destroy(); resolve(true); });  // no response → free
+    s.once("connect", () => {
+      s.destroy();
+      resolve(false);
+    }); // something listening → in use
+    s.once("error", () => {
+      s.destroy();
+      resolve(true);
+    }); // ECONNREFUSED → free
+    s.once("timeout", () => {
+      s.destroy();
+      resolve(true);
+    }); // no response → free
     s.connect(port, "127.0.0.1");
   });
 }
@@ -57,10 +67,9 @@ export async function findFreePort(start: number, maxScan = MAX_PORT_SCAN): Prom
  * Open a URL in the user's browser without throwing back into the caller.
  */
 export function openUrl(url: string): void {
-  const [cmd, args]: [string, string[]] =
-    process.platform === "win32"
-      ? ["cmd.exe", ["/c", "start", "", url]]
-      : [process.platform === "linux" ? "xdg-open" : "open", [url]];
+  const [cmd, args]: [string, string[]] = isWindows()
+    ? ["cmd.exe", ["/c", "start", "", url]]
+    : [isLinux() ? "xdg-open" : "open", [url]];
   const browser = spawn(cmd, args, { stdio: "ignore" });
   browser.on("error", (err) => {
     console.warn(
@@ -68,12 +77,11 @@ export function openUrl(url: string): void {
         cmd,
         args,
         action: `open ${url} in a browser`,
-        installHints:
-          process.platform === "linux"
-            ? ["Install xdg-utils so `xdg-open` is available on PATH."]
-            : process.platform === "win32"
-              ? []
-              : [],
+        installHints: isLinux()
+          ? ["Install xdg-utils so `xdg-open` is available on PATH."]
+          : isWindows()
+            ? []
+            : [],
       }).message,
     );
   });
@@ -145,8 +153,11 @@ export async function buildDashboardEnv(
 
   // If explicit ports provided (config or env var), use them directly.
   // Otherwise, auto-detect an available pair starting from the default.
-  const explicitTerminal = terminalPort ?? (env["TERMINAL_PORT"] ? parseInt(env["TERMINAL_PORT"], 10) : undefined);
-  const explicitDirect = directTerminalPort ?? (env["DIRECT_TERMINAL_PORT"] ? parseInt(env["DIRECT_TERMINAL_PORT"], 10) : undefined);
+  const explicitTerminal =
+    terminalPort ?? (env["TERMINAL_PORT"] ? parseInt(env["TERMINAL_PORT"], 10) : undefined);
+  const explicitDirect =
+    directTerminalPort ??
+    (env["DIRECT_TERMINAL_PORT"] ? parseInt(env["DIRECT_TERMINAL_PORT"], 10) : undefined);
 
   let resolvedTerminal: number;
   let resolvedDirect: number;
@@ -202,8 +213,8 @@ export function findWebDir(): string {
     }
     throw new Error(
       "Could not find @aoagents/ao-web package.\n" +
-      "  If installed via npm:    npm install -g @aoagents/ao\n" +
-      "  If cloned from source:   pnpm install && pnpm build",
+        "  If installed via npm:    npm install -g @aoagents/ao\n" +
+        "  If cloned from source:   pnpm install && pnpm build",
     );
   }
 }
diff --git a/packages/web/server/direct-terminal-ws.ts b/packages/web/server/direct-terminal-ws.ts
index e9a04dd21..d8ebb63b0 100644
--- a/packages/web/server/direct-terminal-ws.ts
+++ b/packages/web/server/direct-terminal-ws.ts
@@ -17,14 +17,17 @@ import {
 
 export interface DirectTerminalServer {
   server: Server;
-  shutdown: () => void;
+  shutdown: (onClosed?: () => void) => void;
 }
 
 function isRemoteAuthAllowed(url: URL, initialConfiguredAuth: RemoteAuthCredentials): boolean {
   const { username, password: expectedPassword } = activeRemoteAuth(initialConfiguredAuth);
   if (!expectedPassword) return true;
 
-  return verifyRemoteWsToken(url.searchParams.get("auth_token"), { username, password: expectedPassword });
+  return verifyRemoteWsToken(url.searchParams.get("auth_token"), {
+    username,
+    password: expectedPassword,
+  });
 }
 
 /**
@@ -89,7 +92,12 @@ export function createDirectTerminalServer(tmuxPath?: string | null): DirectTerm
     }
   });
 
-  function shutdown() {
+  let shuttingDown = false;
+
+  function shutdown(onClosed?: () => void) {
+    if (shuttingDown) return;
+    shuttingDown = true;
+
     // Terminate all connected mux clients — this triggers their 'close' events
     // which unsubscribe terminal callbacks and kill PTY processes.
     if (muxWss) {
@@ -98,7 +106,12 @@ export function createDirectTerminalServer(tmuxPath?: string | null): DirectTerm
       }
       muxWss.close();
     }
-    server.close();
+    server.close((err?: Error & { code?: string }) => {
+      if (err && err.code !== "ERR_SERVER_NOT_RUNNING") {
+        console.error("[DirectTerminal] Error during shutdown:", err);
+      }
+      onClosed?.();
+    });
   }
 
   return { server, shutdown };
@@ -125,19 +138,27 @@ if (isMainModule) {
   }
 
   const { server, shutdown } = createDirectTerminalServer(TMUX);
+  let shuttingDown = false;
 
   server.listen(PORT, () => {
     console.log(`[DirectTerminal] WebSocket server listening on port ${PORT}`);
   });
 
   function handleShutdown(signal: string) {
+    if (shuttingDown) return;
+    shuttingDown = true;
+
     console.log(`[DirectTerminal] Received ${signal}, shutting down...`);
-    shutdown();
     const forceExitTimer = setTimeout(() => {
       console.error("[DirectTerminal] Forced shutdown after timeout");
       process.exit(1);
     }, 5000);
     forceExitTimer.unref();
+
+    shutdown(() => {
+      clearTimeout(forceExitTimer);
+      process.exit(0);
+    });
   }
 
   process.on("SIGINT", () => handleShutdown("SIGINT"));
diff --git a/packages/web/src/middleware.test.ts b/packages/web/src/middleware.test.ts
index ec05c9aac..b6bc5b4f0 100644
--- a/packages/web/src/middleware.test.ts
+++ b/packages/web/src/middleware.test.ts
@@ -84,6 +84,36 @@ describe("remote auth middleware", () => {
     expect(response.status).toBe(200);
   });
 
+  it("requires credentials for proxied requests even when the socket is loopback", () => {
+    vi.stubEnv("AO_REMOTE_AUTH_USER", "ao");
+    vi.stubEnv("AO_REMOTE_AUTH_PASSWORD", "secret");
+    vi.stubEnv("AO_TRUST_REMOTE_ADDRESS_HEADER", "1");
+
+    const response = middleware(
+      request("/api/projects", undefined, {
+        "x-ao-remote-address": "127.0.0.1",
+        "x-forwarded-for": "203.0.113.10",
+      }),
+    );
+
+    expect(response.status).toBe(401);
+  });
+
+  it("requires credentials for Cloudflare-proxied requests from loopback", () => {
+    vi.stubEnv("AO_REMOTE_AUTH_USER", "ao");
+    vi.stubEnv("AO_REMOTE_AUTH_PASSWORD", "secret");
+    vi.stubEnv("AO_TRUST_REMOTE_ADDRESS_HEADER", "1");
+
+    const response = middleware(
+      request("/api/projects", undefined, {
+        "x-ao-remote-address": "::1",
+        "cf-connecting-ip": "203.0.113.10",
+      }),
+    );
+
+    expect(response.status).toBe(401);
+  });
+
   it("ignores the loopback socket header unless the AO server marked it trusted", () => {
     vi.stubEnv("AO_REMOTE_AUTH_USER", "ao");
     vi.stubEnv("AO_REMOTE_AUTH_PASSWORD", "secret");
diff --git a/packages/web/src/middleware.ts b/packages/web/src/middleware.ts
index 669e59fc7..b91c87bd7 100644
--- a/packages/web/src/middleware.ts
+++ b/packages/web/src/middleware.ts
@@ -60,6 +60,14 @@ function isLoopbackAddress(address: string | undefined): boolean {
   );
 }
 
+function hasProxyHeaders(request: NextRequest): boolean {
+  return (
+    request.headers.has("x-forwarded-for") ||
+    request.headers.has("x-real-ip") ||
+    request.headers.has("cf-connecting-ip")
+  );
+}
+
 export function middleware(request: NextRequest) {
   const password = remoteAuthPassword();
   const requestIp =
@@ -67,7 +75,8 @@ export function middleware(request: NextRequest) {
     (process.env["AO_TRUST_REMOTE_ADDRESS_HEADER"] === "1"
       ? (request.headers.get("x-ao-remote-address") ?? undefined)
       : undefined);
-  if (!password || isPublicAsset(request.nextUrl.pathname) || isLoopbackAddress(requestIp)) {
+  const allowLoopbackBypass = isLoopbackAddress(requestIp) && !hasProxyHeaders(request);
+  if (!password || isPublicAsset(request.nextUrl.pathname) || allowLoopbackBypass) {
     return NextResponse.next();
   }