diff --git a/akka-actor-tests/src/test/scala/akka/pattern/AskSpec.scala b/akka-actor-tests/src/test/scala/akka/pattern/AskSpec.scala
index 191892c90a..3ab2c2a3bd 100644
--- a/akka-actor-tests/src/test/scala/akka/pattern/AskSpec.scala
+++ b/akka-actor-tests/src/test/scala/akka/pattern/AskSpec.scala
@@ -44,14 +44,14 @@ class AskSpec extends AkkaSpec {
       f.isCompleted should be(true)
       intercept[IllegalArgumentException] {
         Await.result(f, timeout.duration)
-      }.getMessage should be("Unsupported recipient ActorRef type, question not sent to [null]")
+      }.getMessage should be("Unsupported recipient ActorRef type, question not sent to [null]. Sender[null] sent the message of type \"java.lang.Double\".")
     }
 
     "return broken promises on 0 timeout" in {
       implicit val timeout = Timeout(0 seconds)
       val echo = system.actorOf(Props(new Actor { def receive = { case x ⇒ sender() ! x } }))
       val f = echo ? "foo"
-      val expectedMsg = "Timeout length must not be negative, question not sent to [%s]" format echo
+      val expectedMsg = "Timeout length must not be negative, question not sent to [%s]. Sender[null] sent the message of type \"java.lang.String\"." format echo
       intercept[IllegalArgumentException] {
         Await.result(f, timeout.duration)
       }.getMessage should be(expectedMsg)
@@ -61,7 +61,7 @@ class AskSpec extends AkkaSpec {
       implicit val timeout = Timeout(-1000 seconds)
       val echo = system.actorOf(Props(new Actor { def receive = { case x ⇒ sender() ! x } }))
       val f = echo ? "foo"
-      val expectedMsg = "Timeout length must not be negative, question not sent to [%s]" format echo
+      val expectedMsg = "Timeout length must not be negative, question not sent to [%s]. Sender[null] sent the message of type \"java.lang.String\"." format echo
       intercept[IllegalArgumentException] {
         Await.result(f, timeout.duration)
       }.getMessage should be(expectedMsg)
@@ -84,6 +84,23 @@ class AskSpec extends AkkaSpec {
       }.getMessage should include(timeout.duration.toMillis.toString)
     }
 
+    "include sender information in AskTimeout" in {
+      implicit val timeout = Timeout(0.5 seconds)
+      implicit val sender = system.actorOf(Props.empty)
+      val f = system.actorOf(Props.empty) ? "noreply"
+      intercept[AskTimeoutException] {
+        Await.result(f, 1 second)
+      }.getMessage.contains(sender.toString) should be(true)
+    }
+
+    "include message class information in AskTimeout" in {
+      implicit val timeout = Timeout(0.5 seconds)
+      val f = system.actorOf(Props.empty) ? "noreply"
+      intercept[AskTimeoutException] {
+        Await.result(f, 1 second)
+      }.getMessage.contains("\"java.lang.String\"") should be(true)
+    }
+
     "work for ActorSelection" in {
       implicit val timeout = Timeout(5 seconds)
       import system.dispatcher
diff --git a/akka-actor/src/main/scala/akka/pattern/AskSupport.scala b/akka-actor/src/main/scala/akka/pattern/AskSupport.scala
index 3291d9766c..0340c46eb7 100644
--- a/akka-actor/src/main/scala/akka/pattern/AskSupport.scala
+++ b/akka-actor/src/main/scala/akka/pattern/AskSupport.scala
@@ -73,6 +73,8 @@ trait AskSupport {
    *
    */
   def ask(actorRef: ActorRef, message: Any)(implicit timeout: Timeout): Future[Any] = actorRef ? message
+  def ask(actorRef: ActorRef, message: Any, sender: ActorRef)(implicit timeout: Timeout): Future[Any] =
+    actorRef.?(message)(timeout, sender)
 
   /**
    * Import this implicit conversion to gain `?` and `ask` methods on
@@ -119,6 +121,8 @@ trait AskSupport {
    *
    */
   def ask(actorSelection: ActorSelection, message: Any)(implicit timeout: Timeout): Future[Any] = actorSelection ? message
+  def ask(actorSelection: ActorSelection, message: Any, sender: ActorRef)(implicit timeout: Timeout): Future[Any] =
+    actorSelection.?(message)(timeout, sender)
 }
 
 /*
@@ -126,22 +130,22 @@ trait AskSupport {
  */
 final class AskableActorRef(val actorRef: ActorRef) extends AnyVal {
 
-  def ask(message: Any)(implicit timeout: Timeout): Future[Any] = actorRef match {
+  def ask(message: Any)(implicit timeout: Timeout, sender: ActorRef = Actor.noSender): Future[Any] = actorRef match {
     case ref: InternalActorRef if ref.isTerminated ⇒
       actorRef ! message
-      Future.failed[Any](new AskTimeoutException(s"Recipient[$actorRef] had already been terminated."))
+      Future.failed[Any](new AskTimeoutException(s"""Recipient[$actorRef] had already been terminated. Sender[$sender] sent the message of type "${message.getClass.getName}"."""))
     case ref: InternalActorRef ⇒
       if (timeout.duration.length <= 0)
-        Future.failed[Any](new IllegalArgumentException(s"Timeout length must not be negative, question not sent to [$actorRef]"))
+        Future.failed[Any](new IllegalArgumentException(s"""Timeout length must not be negative, question not sent to [$actorRef]. Sender[$sender] sent the message of type "${message.getClass.getName}"."""))
       else {
-        val a = PromiseActorRef(ref.provider, timeout, targetName = actorRef.toString)
+        val a = PromiseActorRef(ref.provider, timeout, targetName = actorRef.toString, message, sender)
         actorRef.tell(message, a)
         a.result.future
       }
-    case _ ⇒ Future.failed[Any](new IllegalArgumentException(s"Unsupported recipient ActorRef type, question not sent to [$actorRef]"))
+    case _ ⇒ Future.failed[Any](new IllegalArgumentException(s"""Unsupported recipient ActorRef type, question not sent to [$actorRef]. Sender[$sender] sent the message of type "${message.getClass.getName}"."""))
   }
 
-  def ?(message: Any)(implicit timeout: Timeout): Future[Any] = ask(message)(timeout)
+  def ?(message: Any)(implicit timeout: Timeout, sender: ActorRef = Actor.noSender): Future[Any] = ask(message)(timeout, sender)
 }
 
 /*
@@ -149,20 +153,20 @@ final class AskableActorRef(val actorRef: ActorRef) extends AnyVal {
  */
 final class AskableActorSelection(val actorSel: ActorSelection) extends AnyVal {
 
-  def ask(message: Any)(implicit timeout: Timeout): Future[Any] = actorSel.anchor match {
+  def ask(message: Any)(implicit timeout: Timeout, sender: ActorRef = Actor.noSender): Future[Any] = actorSel.anchor match {
     case ref: InternalActorRef ⇒
       if (timeout.duration.length <= 0)
         Future.failed[Any](
-          new IllegalArgumentException(s"Timeout length must not be negative, question not sent to [$actorSel]"))
+          new IllegalArgumentException(s"""Timeout length must not be negative, question not sent to [$actorSel]. Sender[$sender] sent the message of type "${message.getClass.getName}"."""))
       else {
-        val a = PromiseActorRef(ref.provider, timeout, targetName = actorSel.toString)
+        val a = PromiseActorRef(ref.provider, timeout, targetName = actorSel.toString, message, sender)
         actorSel.tell(message, a)
         a.result.future
       }
-    case _ ⇒ Future.failed[Any](new IllegalArgumentException(s"Unsupported recipient ActorRef type, question not sent to [$actorSel]"))
+    case _ ⇒ Future.failed[Any](new IllegalArgumentException(s"""Unsupported recipient ActorRef type, question not sent to [$actorSel]. Sender[$sender] sent the message of type "${message.getClass.getName}"."""))
   }
 
-  def ?(message: Any)(implicit timeout: Timeout): Future[Any] = ask(message)(timeout)
+  def ?(message: Any)(implicit timeout: Timeout, sender: ActorRef = Actor.noSender): Future[Any] = ask(message)(timeout, sender)
 }
 
 /**
@@ -324,13 +328,15 @@ private[akka] object PromiseActorRef {
   private case object Stopped
   private final case class StoppedWithPath(path: ActorPath)
 
-  def apply(provider: ActorRefProvider, timeout: Timeout, targetName: String): PromiseActorRef = {
+  def apply(provider: ActorRefProvider, timeout: Timeout, targetName: String, message: Any, sender: ActorRef = Actor.noSender): PromiseActorRef = {
     val result = Promise[Any]()
     val scheduler = provider.guardian.underlying.system.scheduler
     val a = new PromiseActorRef(provider, result)
     implicit val ec = a.internalCallingThreadExecutionContext
+    val messageClassName = message.getClass.getName
     val f = scheduler.scheduleOnce(timeout.duration) {
-      result tryComplete Failure(new AskTimeoutException(s"Ask timed out on [$targetName] after [${timeout.duration.toMillis} ms]"))
+      result tryComplete Failure(
+        new AskTimeoutException(s"""Ask timed out on [$targetName] after [${timeout.duration.toMillis} ms]. Sender[$sender] sent message of type "$messageClassName"."""))
     }
     result.future onComplete { _ ⇒ try a.stop() finally f.cancel() }
     a
diff --git a/akka-actor/src/main/scala/akka/pattern/GracefulStopSupport.scala b/akka-actor/src/main/scala/akka/pattern/GracefulStopSupport.scala
index ed60682298..af64d0fef6 100644
--- a/akka-actor/src/main/scala/akka/pattern/GracefulStopSupport.scala
+++ b/akka-actor/src/main/scala/akka/pattern/GracefulStopSupport.scala
@@ -49,7 +49,7 @@ trait GracefulStopSupport {
     if (target.isTerminated) Future successful true
     else {
       val internalTarget = target.asInstanceOf[InternalActorRef]
-      val ref = PromiseActorRef(internalTarget.provider, Timeout(timeout), targetName = target.toString)
+      val ref = PromiseActorRef(internalTarget.provider, Timeout(timeout), targetName = target.toString, message = stopMessage)
       internalTarget.sendSystemMessage(Watch(internalTarget, ref))
       target.tell(stopMessage, Actor.noSender)
       ref.result.future.transform(
diff --git a/akka-remote/src/main/scala/akka/remote/transport/ThrottlerTransportAdapter.scala b/akka-remote/src/main/scala/akka/remote/transport/ThrottlerTransportAdapter.scala
index 02ad18ff28..4d2c1a77a6 100644
--- a/akka-remote/src/main/scala/akka/remote/transport/ThrottlerTransportAdapter.scala
+++ b/akka-remote/src/main/scala/akka/remote/transport/ThrottlerTransportAdapter.scala
@@ -298,7 +298,7 @@ private[transport] class ThrottlerManager(wrappedTransport: Transport) extends A
     if (target.isTerminated) Future successful SetThrottleAck
     else {
       val internalTarget = target.asInstanceOf[InternalActorRef]
-      val ref = PromiseActorRef(internalTarget.provider, timeout, target.toString)
+      val ref = PromiseActorRef(internalTarget.provider, timeout, target.toString, mode)
       internalTarget.sendSystemMessage(Watch(internalTarget, ref))
       target.tell(mode, ref)
       ref.result.future.transform({