diff --git a/clientserver/src/main/java/net/rptools/clientserver/simple/server/SocketServer.java b/clientserver/src/main/java/net/rptools/clientserver/simple/server/SocketServer.java
index c7341d169f..4ed70b9dbb 100644
--- a/clientserver/src/main/java/net/rptools/clientserver/simple/server/SocketServer.java
+++ b/clientserver/src/main/java/net/rptools/clientserver/simple/server/SocketServer.java
@@ -39,6 +39,9 @@ public SocketServer(int port) {
   @Override
   public void start() throws IOException {
     var serverSocket = new ServerSocket(port);
+    if (serverSocket.getLocalPort() == -1) {
+      throw new AssertionError("Socket not bound yet");
+    }
     // If the above throws, it will be as though we never started.
 
     socket = serverSocket;
@@ -70,6 +73,16 @@ public String getError() {
     return null;
   }
 
+  /** Get the port of the socket the server is running on or -1. */
+  public int getPort() {
+    // NOTE: We do not use this.port because the socket's bound port can be different
+    if (socket == null || socket.isClosed()) {
+      return -1;
+    }
+
+    return socket.getLocalPort();
+  }
+
   ////
   // Threads
   private static class ListeningThread extends Thread {
diff --git a/src/main/java/net/rptools/clientserver/ConnectionFactory.java b/src/main/java/net/rptools/clientserver/ConnectionFactory.java
index ff9518ba7c..8cedbe399b 100644
--- a/src/main/java/net/rptools/clientserver/ConnectionFactory.java
+++ b/src/main/java/net/rptools/clientserver/ConnectionFactory.java
@@ -15,6 +15,7 @@
 package net.rptools.clientserver;
 
 import java.awt.EventQueue;
+import javax.annotation.Nonnull;
 import javax.annotation.Nullable;
 import net.rptools.clientserver.simple.connection.Connection;
 import net.rptools.clientserver.simple.connection.SocketConnection;
@@ -49,6 +50,7 @@ public void onLoginError() {
         });
   }
 
+  @Nonnull
   public Server createServer(@Nullable ServerConfig config) {
     if (config == null) {
       return new NilServer();
diff --git a/src/main/java/net/rptools/maptool/server/MapToolServer.java b/src/main/java/net/rptools/maptool/server/MapToolServer.java
index ef4729fb9b..dfa073c3ad 100644
--- a/src/main/java/net/rptools/maptool/server/MapToolServer.java
+++ b/src/main/java/net/rptools/maptool/server/MapToolServer.java
@@ -28,9 +28,12 @@
 import net.rptools.clientserver.simple.DisconnectHandler;
 import net.rptools.clientserver.simple.MessageHandler;
 import net.rptools.clientserver.simple.connection.Connection;
+import net.rptools.clientserver.simple.server.NilServer;
 import net.rptools.clientserver.simple.server.Router;
 import net.rptools.clientserver.simple.server.Server;
 import net.rptools.clientserver.simple.server.ServerObserver;
+import net.rptools.clientserver.simple.server.SocketServer;
+import net.rptools.clientserver.simple.server.WebRTCServer;
 import net.rptools.maptool.client.AppConstants;
 import net.rptools.maptool.client.MapTool;
 import net.rptools.maptool.client.MapToolRegistry;
@@ -69,7 +72,7 @@ public enum State {
   }
 
   @Nonnull private final String serviceIdentifier;
-  private final Server server;
+  @Nonnull private final Server server;
   private final MessageHandler messageHandler;
   private final Router router;
   private final ServerConfig config;
@@ -199,7 +202,11 @@ public String getName() {
   }
 
   public int getPort() {
-    return config == null ? -1 : config.getPort();
+    return switch (server) {
+      case NilServer s -> -1;
+      case SocketServer s -> s.getPort();
+      case WebRTCServer s -> -1;
+    };
   }
 
   /**
@@ -363,8 +370,8 @@ public void stop() {
     }
 
     // Close UPnP port mapping if used
-    if (useUPnP && config != null) {
-      int port = config.getPort();
+    int port;
+    if (useUPnP && (port = getPort()) != -1) {
       UPnPUtil.closePort(port);
     }
 
@@ -401,12 +408,13 @@ public void start() throws IOException {
     }
 
     // Use UPnP to open port in router
-    if (useUPnP && config != null) {
+    int port = getPort();
+    if (useUPnP && port != -1) {
       MapTool.getFrame()
           .showFilledGlassPane(
               new StaticMessageDialog(I18N.getText("msg.info.server.upnp.discovering")));
       try {
-        UPnPUtil.openPort(config.getPort());
+        UPnPUtil.openPort(port);
       } finally {
         MapTool.getFrame().hideGlassPane();
       }
@@ -417,11 +425,11 @@ public void start() throws IOException {
       try {
         MapToolRegistry.RegisterResponse result =
             MapToolRegistry.getInstance()
-                .registerInstance(config.getServerName(), config.getPort(), config.getUseWebRTC());
+                .registerInstance(config.getServerName(), port, config.getUseWebRTC());
         if (result == MapToolRegistry.RegisterResponse.NAME_EXISTS) {
           MapTool.showError("msg.error.alreadyRegistered");
         } else {
-          heartbeatThread = new HeartbeatThread(config.getPort());
+          heartbeatThread = new HeartbeatThread(port);
           heartbeatThread.start();
         }
         // TODO: I don't like this
@@ -430,8 +438,8 @@ public void start() throws IOException {
       }
     }
 
-    if (serviceIdentifier != null && config != null) {
-      announcer = new ServiceAnnouncer(serviceIdentifier, config.getPort(), AppConstants.SERVICE_GROUP);
+    if (serviceIdentifier != null && port != -1) {
+      announcer = new ServiceAnnouncer(serviceIdentifier, port, AppConstants.SERVICE_GROUP);
       announcer.start();
     }