diff --git a/src/__tests__/__snapshots__/server.http.test.ts.snap b/src/__tests__/__snapshots__/server.http.test.ts.snap
index 40071dbd..cb1984ae 100644
--- a/src/__tests__/__snapshots__/server.http.test.ts.snap
+++ b/src/__tests__/__snapshots__/server.http.test.ts.snap
@@ -298,16 +298,30 @@ exports[`startHttpTransport should start HTTP server, with port and host: server
       [Function],
     ],
   ],
-  "setupHandlers": [
-    [
-      "connection",
-      [Function],
+  "setupHandlers": {
+    "off": [
+      [
+        "error",
+        [Function],
+      ],
     ],
-    [
-      "error",
-      [Function],
+    "on": [
+      [
+        "connection",
+        [Function],
+      ],
+      [
+        "error",
+        [Function],
+      ],
     ],
-  ],
+    "once": [
+      [
+        "error",
+        [Function],
+      ],
+    ],
+  },
   "setupServer": [
     [
       {
@@ -315,11 +329,6 @@ exports[`startHttpTransport should start HTTP server, with port and host: server
         "sessionId": "test-session-123",
       },
     ],
-    [
-      3000,
-      "localhost",
-      [Function],
-    ],
   ],
   "setupTransport": [
     [
diff --git a/src/__tests__/server.http.test.ts b/src/__tests__/server.http.test.ts
index 68b12138..0cd4e6d2 100644
--- a/src/__tests__/server.http.test.ts
+++ b/src/__tests__/server.http.test.ts
@@ -28,7 +28,10 @@ describe('getProcessOnPort', () => {
 
 describe('startHttpTransport', () => {
   const mockFunction = jest.fn();
-  const mockEventHandler = jest.fn();
+  const mockOnHandler = jest.fn();
+  const mockOnceHandler = jest.fn();
+  const mockOffHandler = jest.fn();
+  const mockListen = jest.fn();
   const mockServerClose = jest.fn();
   let mockRequestHandler: ((req: any, res: any) => void) | undefined;
   let mockServer: any;
@@ -41,8 +44,10 @@ describe('startHttpTransport', () => {
       registerTool: mockFunction
     };
     mockHttpServer = {
-      on: mockEventHandler,
-      listen: mockFunction.mockImplementation((_port: any, _host: any, callback: any) => {
+      on: mockOnHandler,
+      once: mockOnceHandler,
+      off: mockOffHandler,
+      listen: mockListen.mockImplementation((_port: any, _host: any, callback: any) => {
         if (callback) {
           callback();
         }
@@ -78,11 +83,43 @@ describe('startHttpTransport', () => {
     expect({
       setupServer: mockFunction.mock.calls,
       setupTransport: MockStreamableHTTPServerTransport.mock.calls,
-      setupHandlers: mockEventHandler.mock.calls,
+      setupHandlers: {
+        on: mockOnHandler.mock.calls,
+        once: mockOnceHandler.mock.calls,
+        off: mockOffHandler.mock.calls
+      },
       serverClose: mockServerClose.mock.calls
     }).toMatchSnapshot('server setup');
   });
 
+  it('should reject startup on EADDRINUSE error', async () => {
+    mockHttpServer.listen.mockImplementation(() => {
+      const errorHandler = mockHttpServer.once.mock.calls.find((call: any) => call[0] === 'error')?.[1];
+
+      if (errorHandler) {
+        const err: any = new Error('Address in use');
+
+        err.code = 'EADDRINUSE';
+        errorHandler(err);
+      }
+    });
+
+    await expect(
+      startHttpTransport(mockServer, { http: { port: 5000, host: 'localhost' } } as any)
+    ).rejects.toThrow('Port 5000 is already in use');
+  });
+
+  it('should log runtime error emitted after startup without throwing unhandled exception', async () => {
+    const server = await startHttpTransport(mockServer, { http: { port: 3000, host: 'localhost' } } as any);
+
+    const runtimeErrorHandler = mockHttpServer.on.mock.calls.find((call: any) => call[0] === 'error')?.[1];
+
+    expect(runtimeErrorHandler).toBeDefined();
+    await expect(runtimeErrorHandler(new Error('Connection reset'))).resolves.toBeUndefined();
+
+    await server.close();
+  });
+
   it.each([
     {
       description: 'with invalid port',
diff --git a/src/server.http.ts b/src/server.http.ts
index dbd34f4c..98ea39e0 100644
--- a/src/server.http.ts
+++ b/src/server.http.ts
@@ -214,17 +214,9 @@ const startHttpTransport = async (mcpServer: McpServer, options = getOptions()):
 
   // Start the server. Port conflicts will be handled in the error handler below
   await new Promise<void>((resolve, reject) => {
-    server.listen(http.port, http.host, () => {
-      log.info(`${name} server running on http://${http.host}:${getPort()}`);
-      resolve();
-    });
+    const onStartupError = async (error: NodeJS.ErrnoException) => {
+      server.off('error', onStartupError);
 
-    server.on('connection', socket => {
-      connections.add(socket);
-      socket.on('close', () => connections.delete(socket));
-    });
-
-    server.on('error', async (error: NodeJS.ErrnoException) => {
       if (error.code === 'EADDRINUSE') {
         const processInfo = await getProcessOnPort(http.port);
         const errorMessage = `Port ${http.port} is already in use${processInfo ? ` by PID ${processInfo.pid}` : ''}.`;
@@ -235,9 +227,26 @@ const startHttpTransport = async (mcpServer: McpServer, options = getOptions()):
         log.error(`HTTP server error: ${error}`);
         reject(error);
       }
+    };
+
+    server.once('error', onStartupError);
+
+    server.listen(http.port, http.host, () => {
+      server.off('error', onStartupError);
+      log.info(`${name} server running on http://${http.host}:${getPort()}`);
+      resolve();
     });
   });
 
+  server.on('connection', socket => {
+    connections.add(socket);
+    socket.on('close', () => connections.delete(socket));
+  });
+
+  server.on('error', async (error: NodeJS.ErrnoException) => {
+    log.error(`HTTP server runtime error: ${error.message || error}`);
+  });
+
   return {
     port: getPort(),
     close: async () => {