diff --git a/akka-actor-tests/src/test/scala/akka/actor/IOActor.scala b/akka-actor-tests/src/test/scala/akka/actor/IOActor.scala
index c10e807f5a..c21a9b2662 100644
--- a/akka-actor-tests/src/test/scala/akka/actor/IOActor.scala
+++ b/akka-actor-tests/src/test/scala/akka/actor/IOActor.scala
@@ -15,6 +15,7 @@ import akka.pattern.ask
 import java.net.{ Socket, InetSocketAddress, InetAddress, SocketAddress }
 import scala.util.Failure
 import scala.annotation.tailrec
+import akka.AkkaException
 
 object IOActorSpec {
 
@@ -402,6 +403,17 @@ class IOActorSpec extends AkkaSpec with DefaultTimeout {
       expectMsgType[Status.Failure](1 seconds)
     }
 
+    "fail when binding to already bound port and report port in failure" in {
+      implicit val self = testActor
+      IOManager(system).listen(new InetSocketAddress("localhost", 0))
+      val boundTo = expectMsgType[IO.Listening].address.asInstanceOf[InetSocketAddress]
+      IOManager(system).listen(boundTo)
+      val exc = expectMsgType[Status.Failure].cause
+      exc.getClass must be(classOf[AkkaException])
+      exc.getMessage must include("Address already in use")
+      exc.getMessage must include(boundTo.getPort.toString)
+    }
+
   }
 
 }
diff --git a/akka-actor/src/main/scala/akka/actor/IO.scala b/akka-actor/src/main/scala/akka/actor/IO.scala
index 4ae9a9515c..30f9e3d3cc 100644
--- a/akka-actor/src/main/scala/akka/actor/IO.scala
+++ b/akka-actor/src/main/scala/akka/actor/IO.scala
@@ -5,7 +5,6 @@ package akka.actor
 
 import language.higherKinds
 import language.postfixOps
-
 import scala.collection.immutable
 import scala.concurrent.{ ExecutionContext, Future }
 import scala.concurrent.duration.Duration
@@ -30,6 +29,7 @@ import java.util.UUID
 import java.io.{ EOFException, IOException }
 import akka.actor.IOManager.Settings
 import akka.actor.IO.Chunk
+import akka.AkkaException
 
 /**
  * IO messages and iteratees.
@@ -1038,10 +1038,10 @@ final class IOManagerActor(val settings: Settings) extends Actor with ActorLoggi
         channel register (selector, OP_ACCEPT, server)
         server.owner ! IO.Listening(server, sock.getLocalSocketAddress())
       } catch {
-        case NonFatal(e) ⇒ {
-          channel close ()
-          sender ! Status.Failure(e)
-        }
+        case NonFatal(e) ⇒
+          try { channel close () } finally {
+            sender ! Status.Failure(new AkkaException(s"Failed to listen to [${address}], due to [${e.getMessage}]", e))
+          }
       }
       run()
 
@@ -1054,10 +1054,10 @@ final class IOManagerActor(val settings: Settings) extends Actor with ActorLoggi
         channels update (socket, channel)
         channel register (selector, OP_CONNECT | OP_READ, socket)
       } catch {
-        case NonFatal(e) ⇒ {
-          channel close ()
-          sender ! Status.Failure(e)
-        }
+        case NonFatal(e) ⇒
+          try { channel close () } finally {
+            sender ! Status.Failure(e)
+          }
       }
       run()