diff --git a/client/bin/client.js b/client/bin/client.js
index 2a7419e66..28c31d1bb 100755
--- a/client/bin/client.js
+++ b/client/bin/client.js
@@ -5,10 +5,40 @@ import { join, dirname } from "path";
 import { fileURLToPath } from "url";
 import handler from "serve-handler";
 import http from "http";
+import net from "net";
 
 const __dirname = dirname(fileURLToPath(import.meta.url));
 const distPath = join(__dirname, "../dist");
 
+const port = parseInt(process.env.CLIENT_PORT || "6274", 10);
+const host = process.env.HOST || "localhost";
+
+// Check port availability before attempting to bind.
+// Prevents confusing EADDRINUSE errors from stale processes.
+function checkPort(targetHost, targetPort) {
+  return new Promise((resolve) => {
+    const tester = net.createServer();
+    tester.once("error", (err) => {
+      resolve(false);
+    });
+    tester.once("listening", () => {
+      tester.close(() => resolve(true));
+    });
+    tester.listen(targetPort, targetHost);
+  });
+}
+
+const portFree = await checkPort(host, port);
+if (!portFree) {
+  console.error(
+    `❌  MCP Inspector PORT IS IN USE at http://${host}:${port} ❌ `,
+  );
+  console.error(
+    `💡 To fix: run "lsof -ti:${port} | xargs kill -9" to free the port, or set CLIENT_PORT to use a different port.`,
+  );
+  process.exit(1);
+}
+
 const server = http.createServer((request, response) => {
   const handlerOptions = {
     public: distPath,
@@ -40,8 +70,6 @@ const server = http.createServer((request, response) => {
   return handler(request, response, handlerOptions);
 });
 
-const port = parseInt(process.env.CLIENT_PORT || "6274", 10);
-const host = process.env.HOST || "localhost";
 server.on("listening", () => {
   const url = process.env.INSPECTOR_URL || `http://${host}:${port}`;
   console.log(`\n🚀 MCP Inspector is up and running at:\n   ${url}\n`);
@@ -58,5 +86,20 @@ server.on("error", (err) => {
   } else {
     throw err;
   }
+  process.exit(1);
 });
+
+// Graceful shutdown: properly close the HTTP server so the port is
+// released immediately instead of lingering in CLOSE_WAIT state.
+function shutdown() {
+  server.close(() => {
+    process.exit(0);
+  });
+  // Force exit if close takes too long (e.g. hanging connections)
+  setTimeout(() => process.exit(0), 3000);
+}
+
+process.on("SIGINT", shutdown);
+process.on("SIGTERM", shutdown);
+
 server.listen(port, host);
diff --git a/server/src/index.ts b/server/src/index.ts
index 4d1fffa29..2b0934e73 100644
--- a/server/src/index.ts
+++ b/server/src/index.ts
@@ -29,6 +29,7 @@ import rateLimit from "express-rate-limit";
 import { findActualExecutable } from "spawn-rx";
 import mcpProxy from "./mcpProxy.js";
 import { randomUUID, randomBytes, timingSafeEqual } from "node:crypto";
+import net from "net";
 import { fileURLToPath } from "url";
 import { dirname, join } from "path";
 import { readFileSync } from "fs";
@@ -822,6 +823,30 @@ const PORT = parseInt(
 );
 const HOST = process.env.HOST || "localhost";
 
+// Check port availability before attempting to bind.
+// Prevents confusing EADDRINUSE errors from stale processes.
+function checkPort(targetHost: string, targetPort: number): Promise<boolean> {
+  return new Promise((resolve) => {
+    const tester = net.createServer();
+    tester.once("error", () => {
+      resolve(false);
+    });
+    tester.once("listening", () => {
+      tester.close(() => resolve(true));
+    });
+    tester.listen(targetPort, targetHost);
+  });
+}
+
+const portFree = await checkPort(HOST, PORT);
+if (!portFree) {
+  console.error(`❌  Proxy Server PORT IS IN USE at port ${PORT} ❌ `);
+  console.error(
+    `💡 To fix: run "lsof -ti:${PORT} | xargs kill -9" to free the port, or set SERVER_PORT to use a different port.`,
+  );
+  process.exit(1);
+}
+
 const server = app.listen(PORT, HOST);
 server.on("listening", () => {
   console.log(`⚙️ Proxy server listening on ${HOST}:${PORT}`);
@@ -844,3 +869,15 @@ server.on("error", (err) => {
   }
   process.exit(1);
 });
+
+// Graceful shutdown: properly close the HTTP server so the port is
+// released immediately instead of lingering in CLOSE_WAIT state.
+function shutdown() {
+  server.close(() => {
+    process.exit(0);
+  });
+  setTimeout(() => process.exit(0), 3000);
+}
+
+process.on("SIGINT", shutdown);
+process.on("SIGTERM", shutdown);