diff --git a/lib/modules/webserver/index.js b/lib/modules/webserver/index.js
index cfd5d7baf..a0b948502 100644
--- a/lib/modules/webserver/index.js
+++ b/lib/modules/webserver/index.js
@@ -17,20 +17,36 @@ class WebServer {
     this.port = options.port || this.webServerConfig.port;
 
     this.events.emit("status", __("Starting Server"));
+
     this.server = new Server({host: this.host, port: this.port});
+    this.testPort(() => {
+      this.listenToCommands();
+      this.registerConsoleCommands();
+      this.server.start((_err, message, port) => {
+        this.logger.info(message);
+        this.port = port;
+        this.setServiceCheck();
+      });
+    });
+  }
 
-    this.setServiceCheck();
-    this.listenToCommands();
-    this.registerConsoleCommands();
-
-    let self = this;
-    this.server.start((_err, message) => self.logger.info(message));
+  testPort(done) {
+    utils.pingEndpoint(this.host, this.port, 'http', 'http', '', (err) => {
+      if (err) { // Port is ok
+        return done();
+      }
+      this.logger.warn(__('Webserver already running on port %s. Assigning an available port', this.port));
+      this.port = 0;
+      this.server.port = 0;
+      done();
+    });
   }
 
   setServiceCheck() {
-    let url = 'http://' + canonicalHost(this.host) + ':' + this.port;
+    const self = this;
 
     this.events.request("services:register", 'Webserver', function (cb) {
+      let url = 'http://' + canonicalHost(self.host) + ':' + self.port;
       utils.checkIsAvailable(url, function (available) {
         let devServer = __('Webserver') + ' (' + url + ')';
         let serverStatus = (available ? 'on' : 'off');
diff --git a/lib/modules/webserver/server.js b/lib/modules/webserver/server.js
index 40356be6b..340f5307c 100644
--- a/lib/modules/webserver/server.js
+++ b/lib/modules/webserver/server.js
@@ -24,12 +24,14 @@ class Server {
       serve(req, res, finalhandler(req, res));
     }).withShutdown();
 
-    let message = __("webserver available at") +
-                    " " +
-                    ("http://" + canonicalHost(this.hostname) +
-                    ":" + this.port).bold.underline.green;
-    this.server.listen(this.port, this.hostname);
-    callback(null, message);
+
+    this.server.listen(this.port, this.hostname, () => {
+      this.port = this.server.address().port;
+      callback(null, __("webserver available at") +
+        " " +
+        ("http://" + canonicalHost(this.hostname) +
+          ":" + this.port).bold.underline.green, this.port);
+    });
   }
 
   stop(callback) {