diff --git a/bin/webpack-dev-server.js b/bin/webpack-dev-server.js
index 224a69d978..a575fb17df 100755
--- a/bin/webpack-dev-server.js
+++ b/bin/webpack-dev-server.js
@@ -113,19 +113,13 @@ function startDevServer(config, options) {
     throw err;
   }
 
-  if (options.socket) {
-    server.listen(options.socket, options.host, (err) => {
-      if (err) {
-        throw err;
-      }
-    });
-  } else {
-    server.listen(options.port, options.host, (err) => {
-      if (err) {
-        throw err;
-      }
-    });
-  }
+  // options.socket does not have a default value, so it will only be set
+  // if the user sets it explicitly
+  server.listen(options.socket || options.port, options.host, (err) => {
+    if (err) {
+      throw err;
+    }
+  });
 }
 
 processOptions(config, argv, (config, options) => {
diff --git a/lib/Server.js b/lib/Server.js
index 1a8f83ea60..1d59bcbca3 100644
--- a/lib/Server.js
+++ b/lib/Server.js
@@ -740,12 +740,12 @@ class Server {
 
     // between setupCallback and userCallback should be any other needed handling,
     // specifically so that things are done in the right order to prevent
-    // backwards compatability issues
+    // backwards compatibility issues
     let userCallbackCalled = false;
-    const userCallback = (err) => {
+    const userCallback = async (err) => {
       if (fn && !userCallbackCalled) {
         userCallbackCalled = true;
-        fn.call(this.listeningApp, err);
+        await fn.call(this.listeningApp, err);
       }
     };
 
@@ -755,9 +755,9 @@ class Server {
       }
     };
 
-    const fullCallback = (err) => {
+    const fullCallback = async (err) => {
       setupCallback();
-      userCallback(err);
+      await userCallback(err);
       onListeningCallback();
     };
 
diff --git a/test/server/Server.test.js b/test/server/Server.test.js
index d54712a087..7fa99b84ce 100644
--- a/test/server/Server.test.js
+++ b/test/server/Server.test.js
@@ -7,6 +7,7 @@ const { noop } = require('webpack-dev-middleware/lib/util');
 const Server = require('../../lib/Server');
 const config = require('../fixtures/simple-config/webpack.config');
 const port = require('../ports-map').Server;
+const timer = require('../helpers/timer');
 
 jest.mock('sockjs/lib/transport');
 
@@ -178,4 +179,28 @@ describe('Server', () => {
       });
     });
   });
+
+  describe('server.listen', () => {
+    it('should complete async callback before calling onListening', (done) => {
+      const callOrder = [];
+      const compiler = webpack(config);
+      const server = new Server(compiler, {
+        onListening: () => {
+          callOrder.push('onListening');
+        },
+        ...baseDevConfig,
+      });
+      server.listen(port, '0.0.0.0', async () => {
+        await timer(1000);
+        callOrder.push('user callback');
+      });
+
+      // we need a timeout because even if the server is done listening,
+      // the compiler might still be compiling
+      setTimeout(() => {
+        expect(callOrder).toMatchSnapshot();
+        server.close(done);
+      }, 5000);
+    });
+  });
 });
diff --git a/test/server/__snapshots__/Server.test.js.snap b/test/server/__snapshots__/Server.test.js.snap
index b39da65eb6..59ec7f1b8f 100644
--- a/test/server/__snapshots__/Server.test.js.snap
+++ b/test/server/__snapshots__/Server.test.js.snap
@@ -59,3 +59,10 @@ Array [
   },
 ]
 `;
+
+exports[`Server server.listen should complete async callback before calling onListening 1`] = `
+Array [
+  "user callback",
+  "onListening",
+]
+`;