diff --git a/CHANGES.txt b/CHANGES.txt
index e99c9ea2d7..df2db42a7c 100644
--- a/CHANGES.txt
+++ b/CHANGES.txt
@@ -1,4 +1,5 @@
 4.0
+ * Report why native_transport_port fails to bind (CASSANDRA-14544)
  * Optimize internode messaging protocol (CASSANDRA-14485)
  * Internode messaging handshake sends wrong messaging version number (CASSANDRA-14540)
  * Add a virtual table to expose active client connections (CASSANDRA-14458)
diff --git a/src/java/org/apache/cassandra/transport/Server.java b/src/java/org/apache/cassandra/transport/Server.java
index 8ef137c44e..45146c4d99 100644
--- a/src/java/org/apache/cassandra/transport/Server.java
+++ b/src/java/org/apache/cassandra/transport/Server.java
@@ -161,7 +161,8 @@ public class Server implements CassandraDaemon.Server
 
         ChannelFuture bindFuture = bootstrap.bind(socket);
         if (!bindFuture.awaitUninterruptibly().isSuccess())
-            throw new IllegalStateException(String.format("Failed to bind port %d on %s.", socket.getPort(), socket.getAddress().getHostAddress()));
+            throw new IllegalStateException(String.format("Failed to bind port %d on %s.", socket.getPort(), socket.getAddress().getHostAddress()),
+                                            bindFuture.cause());
 
         connectionTracker.allChannels.add(bindFuture.channel());
         isRunning.set(true);