diff --git a/dev/src/server/adk_api_server.ts b/dev/src/server/adk_api_server.ts
index a52ad63ab..2e638ad33 100644
--- a/dev/src/server/adk_api_server.ts
+++ b/dev/src/server/adk_api_server.ts
@@ -75,6 +75,45 @@ interface ServerOptions {
   registerProcessors?: (tracerProvider: TracerProvider) => void;
 }
 
+/**
+ * A Node system error: an `Error` that carries an errno string in `code`.
+ *
+ * The `@types/node` package declares this shape only as
+ * `NodeJS.ErrnoException`, in an ambient namespace that the repository's
+ * `no-undef` lint rule rejects.
+ */
+interface SystemError extends Error {
+  code?: string;
+}
+
+/**
+ * Converts a `listen()` failure into the error the caller reports.
+ *
+ * The CLI prints only `error.message`, so a cause the operator can act on has
+ * to be in the message itself. An errno with no better wording than the system
+ * error is returned unchanged.
+ */
+export function toListenError(
+  err: SystemError,
+  host: string,
+  port: number,
+): Error {
+  switch (err.code) {
+    case 'EADDRINUSE':
+      return new Error(`Port ${port} is already in use`, {cause: err});
+    case 'EACCES':
+      return new Error(
+        `Permission denied binding ${host}:${port}. Ports below 1024 need ` +
+          `elevated privileges. Windows also reserves blocks of ports; list ` +
+          `them with "netsh interface ipv4 show excludedportrange ` +
+          `protocol=tcp". Use a different port, or port 0 for any free port.`,
+        {cause: err},
+      );
+    default:
+      return err;
+  }
+}
+
 export class AdkApiServer {
   private readonly host: string;
   private readonly port: number;
@@ -973,15 +1012,8 @@ export class AdkApiServer {
         }
       });
 
-      this.server.on('error', (err: unknown) => {
-        if ((err as {code: string}).code === 'EADDRINUSE') {
-          const error = new Error();
-          error.cause = err;
-          error.message = `Port ${this.port} is already in use`;
-          reject(error);
-        } else {
-          reject(err);
-        }
+      this.server.on('error', (err: SystemError) => {
+        reject(toListenError(err, this.host, this.port));
       });
     });
   }
diff --git a/dev/test/server/adk_api_server_test.ts b/dev/test/server/adk_api_server_test.ts
index d6db712d2..2adad341f 100644
--- a/dev/test/server/adk_api_server_test.ts
+++ b/dev/test/server/adk_api_server_test.ts
@@ -28,6 +28,7 @@ import {z} from 'zod';
 import {
   A2A_AUTH_TOKEN_ENV_VAR,
   AdkApiServer,
+  toListenError,
 } from '../../src/server/adk_api_server.js';
 import {AgentLoader} from '../../src/utils/agent_loader.js';
 
@@ -1256,3 +1257,49 @@ describe('AdkWebServer', () => {
     });
   });
 });
+
+describe('toListenError', () => {
+  it('keeps the in-use wording for EADDRINUSE', () => {
+    const err = Object.assign(
+      new Error('listen EADDRINUSE: address already in use ::1:8000'),
+      {code: 'EADDRINUSE'},
+    );
+
+    const error = toListenError(err, 'localhost', 8000);
+
+    expect(error.message).toBe('Port 8000 is already in use');
+    expect(error.cause).toBe(err);
+  });
+
+  it('explains both causes of EACCES and how to work around them', () => {
+    const err = Object.assign(
+      new Error('listen EACCES: permission denied ::1:80'),
+      {code: 'EACCES'},
+    );
+
+    const error = toListenError(err, 'localhost', 80);
+
+    expect(error.message).toContain('localhost:80');
+    expect(error.message).toContain('below 1024');
+    expect(error.message).toContain(
+      'netsh interface ipv4 show excludedportrange protocol=tcp',
+    );
+    expect(error.message).toContain('port 0');
+    expect(error.message).not.toContain('--port');
+    expect(error.cause).toBe(err);
+  });
+
+  it('passes an unrelated errno through unchanged', () => {
+    const err = Object.assign(new Error('read ECONNRESET'), {
+      code: 'ECONNRESET',
+    });
+
+    expect(toListenError(err, 'localhost', 8000)).toBe(err);
+  });
+
+  it('passes an error with no code through unchanged', () => {
+    const err = new Error('something else went wrong');
+
+    expect(toListenError(err, 'localhost', 8000)).toBe(err);
+  });
+});