@@ -2296,7 +2296,9 @@ class WebpackCLI {
           // needed for `webpack-dev-server@5` typings, which lack the plugin constructor
           const DevServerPlugin = DevServer as unknown as new (options: DevServerConfiguration) => {
             apply(compiler: Compiler | MultiCompiler): void;
+            listen(): Promise<void>;
           };
+          const plugins: InstanceType<typeof DevServerPlugin>[] = [];
 
           const compiler = await this.createCompiler(
             webpackCLIOptions,
@@ -2361,6 +2363,8 @@ class WebpackCLI {
                   setupExitSignals: false,
                 });
 
+                plugins.push(plugin);
+
                 if (isDevServerPerCompiler) {
                   configuration.plugins = [...(configuration.plugins || []), plugin];
                 } else {
@@ -2406,6 +2410,25 @@ class WebpackCLI {
             return;
           }
 
+          // TODO remove it when webpack-dev-server reports listen failures to the compiler
+          // A dev server only logs a failure to listen, e.g. a port already in use, and the
+          // CLI would keep watching without it, so exit like dev servers without plugin
+          // support do
+          for (const plugin of plugins) {
+            const { listen } = plugin;
+
+            plugin.listen = () =>
+              listen.call(plugin).catch((error) => {
+                process.exitCode = 2;
+
+                compiler.close(() => {
+                  process.exit();
+                });
+
+                throw error;
+              });
+          }
+
           // Closing the compiler stops dev servers, failures keep the exit code
           this.#setupGracefulShutdown(compiler, true);
 
 
@@ -3,6 +3,7 @@
 /* eslint-disable jest/require-top-level-describe -- Version-gated describe */
 
 const fs = require("node:fs");
+const net = require("node:net");
 const os = require("node:os");
 const path = require("node:path");
 const [devServerVersion] = require("webpack-dev-server/package.json").version;
@@ -163,6 +164,33 @@ describeDevServer6("serve error handling", () => {
     expect(stdout).toBeFalsy();
   });
 
+  test("should log the error and exit when the port is already in use", async () => {
+    const server = net.createServer();
+
+    await new Promise((resolve) => {
+      server.listen(port, "127.0.0.1", resolve);
+    });
+
+    try {
+      const { exitCode, stderr } = await run(__dirname, [
+        "serve",
+        "--config",
+        "recover.config.js",
+        "--env",
+        `entry=${path.resolve(__dirname, "src/index.js")}`,
+        "--host",
+        "127.0.0.1",
+        "--port",
+        port,
+      ]);
+
+      expect(exitCode).toBe(2);
+      expect(stderr).toContain("EADDRINUSE");
+    } finally {
+      server.close();
+    }
+  });
+
   test("should log the validation error and exit when a middleware option is invalid", async () => {
     const { exitCode, stderr, stdout } = await run(__dirname, [
       "serve",