diff --git a/akka-remote/src/main/scala/akka/remote/RemoteActorRefProvider.scala b/akka-remote/src/main/scala/akka/remote/RemoteActorRefProvider.scala
index 119b406d8f..70bf13e572 100644
--- a/akka-remote/src/main/scala/akka/remote/RemoteActorRefProvider.scala
+++ b/akka-remote/src/main/scala/akka/remote/RemoteActorRefProvider.scala
@@ -497,12 +497,14 @@ private[akka] class RemoteActorRef private[akka] (
   @deprecated("Use context.watch(actor) and receive Terminated(actor)", "2.2")
   override private[akka] def isTerminated: Boolean = false
 
-  private def handleException: Catcher[Unit] = {
+  private def handleException(message: Any, sender: ActorRef): Catcher[Unit] = {
     case e: InterruptedException ⇒
       remote.system.eventStream.publish(Error(e, path.toString, getClass, "interrupted during message send"))
+      remote.system.deadLetters.tell(message, sender)
       Thread.currentThread.interrupt()
     case NonFatal(e) ⇒
       remote.system.eventStream.publish(Error(e, path.toString, getClass, "swallowing exception during message send"))
+      remote.system.deadLetters.tell(message, sender)
   }
 
   /**
@@ -529,11 +531,11 @@ private[akka] class RemoteActorRef private[akka] (
           provider.remoteWatcher ! RemoteWatcher.UnwatchRemote(watchee, watcher)
         case _ ⇒ remote.send(message, OptionVal.None, this)
       }
-    } catch handleException
+    } catch handleException(message, Actor.noSender)
 
   override def !(message: Any)(implicit sender: ActorRef = Actor.noSender): Unit = {
     if (message == null) throw new InvalidMessageException("Message is null")
-    try remote.send(message, OptionVal(sender), this) catch handleException
+    try remote.send(message, OptionVal(sender), this) catch handleException(message, sender)
   }
 
   override def provider: RemoteActorRefProvider = remote.provider
diff --git a/akka-remote/src/main/scala/akka/remote/artery/ArteryTransport.scala b/akka-remote/src/main/scala/akka/remote/artery/ArteryTransport.scala
index 5acdf104be..9edaa01bf2 100644
--- a/akka-remote/src/main/scala/akka/remote/artery/ArteryTransport.scala
+++ b/akka-remote/src/main/scala/akka/remote/artery/ArteryTransport.scala
@@ -9,16 +9,13 @@ import java.nio.channels.DatagramChannel
 import java.util.concurrent.CopyOnWriteArrayList
 import java.util.concurrent.TimeUnit
 import java.util.concurrent.atomic.AtomicLong
-
 import scala.collection.JavaConverters._
-
 import scala.concurrent.Future
 import scala.concurrent.Promise
 import scala.concurrent.duration._
 import scala.util.Failure
 import scala.util.Success
 import scala.util.Try
-
 import akka.Done
 import akka.NotUsed
 import akka.actor.ActorRef
@@ -68,13 +65,10 @@ import org.agrona.IoUtil
 import java.io.File
 import java.net.InetSocketAddress
 import java.nio.channels.{ DatagramChannel, FileChannel }
-
 import akka.remote.artery.OutboundControlJunction.OutboundControlIngress
 import io.aeron.CncFileDescriptor
 import java.util.concurrent.atomic.AtomicLong
-
 import akka.actor.Cancellable
-
 import scala.collection.JavaConverters._
 import akka.stream.ActorMaterializerSettings
 import scala.annotation.tailrec
@@ -331,7 +325,7 @@ private[remote] class ArteryTransport(_system: ExtendedActorSystem, _provider: R
   override def addresses: Set[Address] = _addresses
   override def localAddressForRemote(remote: Address): Address = defaultAddress
   override val log: LoggingAdapter = Logging(system, getClass.getName)
-  private val eventPublisher = new EventPublisher(system, log, remoteSettings.RemoteLifecycleEventsLogLevel)
+  val eventPublisher = new EventPublisher(system, log, remoteSettings.RemoteLifecycleEventsLogLevel)
 
   private val codec: AkkaPduCodec = AkkaPduProtobufCodec
   private val killSwitch: SharedKillSwitch = KillSwitches.shared("transportKillSwitch")
@@ -705,7 +699,8 @@ private[remote] class ArteryTransport(_system: ExtendedActorSystem, _provider: R
   def outboundControl(outboundContext: OutboundContext): Sink[Send, (OutboundControlIngress, Future[Done])] = {
     Flow.fromGraph(killSwitch.flow[Send])
       .via(new OutboundHandshake(outboundContext, handshakeTimeout, handshakeRetryInterval, injectHandshakeInterval))
-      .via(new SystemMessageDelivery(outboundContext, systemMessageResendInterval, remoteSettings.SysMsgBufferSize))
+      .via(new SystemMessageDelivery(outboundContext, system.deadLetters, systemMessageResendInterval,
+        remoteSettings.SysMsgBufferSize))
       .viaMat(new OutboundControlJunction(outboundContext))(Keep.right)
       .via(encoder)
       .toMat(new AeronSink(outboundChannel(outboundContext.remoteAddress), controlStreamId, aeron, taskRunner,
diff --git a/akka-remote/src/main/scala/akka/remote/artery/Association.scala b/akka-remote/src/main/scala/akka/remote/artery/Association.scala
index 8a4e85c5ee..ca90c9a366 100644
--- a/akka-remote/src/main/scala/akka/remote/artery/Association.scala
+++ b/akka-remote/src/main/scala/akka/remote/artery/Association.scala
@@ -36,6 +36,7 @@ import akka.stream.scaladsl.Source
 import akka.util.{ Unsafe, WildcardTree }
 import org.agrona.concurrent.ManyToOneConcurrentArrayQueue
 import akka.util.OptionVal
+import akka.remote.QuarantinedEvent
 
 /**
  * INTERNAL API
@@ -223,6 +224,8 @@ private[remote] class Association(
                 log.warning(
                   "Association to [{}] with UID [{}] is irrecoverably failed. Quarantining address. {}",
                   remoteAddress, u, reason)
+                // FIXME when we complete the switch to Long UID we must use Long here also, issue #20644
+                transport.eventPublisher.notifyListeners(QuarantinedEvent(remoteAddress, u.toInt))
                 // end delivery of system messages to that incarnation after this point
                 send(ClearSystemMessageDelivery, OptionVal.None, dummyRecipient)
                 // try to tell the other system that we have quarantined it
diff --git a/akka-remote/src/main/scala/akka/remote/artery/SystemMessageDelivery.scala b/akka-remote/src/main/scala/akka/remote/artery/SystemMessageDelivery.scala
index a6ba8b25fe..de2ee9da60 100644
--- a/akka-remote/src/main/scala/akka/remote/artery/SystemMessageDelivery.scala
+++ b/akka-remote/src/main/scala/akka/remote/artery/SystemMessageDelivery.scala
@@ -23,6 +23,7 @@ import akka.stream.stage.InHandler
 import akka.stream.stage.OutHandler
 import akka.stream.stage.TimerGraphStageLogic
 import akka.remote.artery.OutboundHandshake.HandshakeReq
+import akka.actor.ActorRef
 
 /**
  * INTERNAL API
@@ -44,6 +45,7 @@ private[akka] object SystemMessageDelivery {
  */
 private[akka] class SystemMessageDelivery(
   outboundContext: OutboundContext,
+  deadLetters:     ActorRef,
   resendInterval:  FiniteDuration,
   maxBufferSize:   Int)
   extends GraphStage[FlowShape[Send, Send]] {
@@ -87,6 +89,8 @@ private[akka] class SystemMessageDelivery(
       }
 
       override def postStop(): Unit = {
+        sendUnacknowledgedToDeadLetters()
+        unacknowledged.clear()
         outboundContext.controlSubject.detach(this)
       }
 
@@ -180,12 +184,14 @@ private[akka] class SystemMessageDelivery(
             } else {
               // buffer overflow
               outboundContext.quarantine(reason = s"System message delivery buffer overflow, size [$maxBufferSize]")
+              deadLetters ! s
               pull(in)
             }
         }
       }
 
       private def clear(): Unit = {
+        sendUnacknowledgedToDeadLetters()
         seqNo = 0L // sequence number for the first message will be 1
         unacknowledged.clear()
         resending.clear()
@@ -193,6 +199,13 @@ private[akka] class SystemMessageDelivery(
         cancelTimer(resendInterval)
       }
 
+      private def sendUnacknowledgedToDeadLetters(): Unit = {
+        val iter = unacknowledged.iterator
+        while (iter.hasNext()) {
+          deadLetters ! iter.next()
+        }
+      }
+
       // OutHandler
       override def onPull(): Unit = {
         if (replyObserverAttached) { // otherwise it will be pulled after attached
diff --git a/akka-remote/src/test/scala/akka/remote/artery/RemoteDeathWatchSpec.scala b/akka-remote/src/test/scala/akka/remote/artery/RemoteDeathWatchSpec.scala
index 7313806127..297cb9fcc0 100644
--- a/akka-remote/src/test/scala/akka/remote/artery/RemoteDeathWatchSpec.scala
+++ b/akka-remote/src/test/scala/akka/remote/artery/RemoteDeathWatchSpec.scala
@@ -72,8 +72,7 @@ class RemoteDeathWatchSpec extends AkkaSpec(RemoteDeathWatchSpec.config) with Im
     }
   }
 
-  // FIXME this is failing with Artery
-  "receive Terminated when watched node is unknown host" ignore {
+  "receive Terminated when watched node is unknown host" in {
     val path = RootActorPath(Address("artery", system.name, "unknownhost", 2552)) / "user" / "subject"
     system.actorOf(Props(new Actor {
       context.watch(context.actorFor(path))
@@ -85,8 +84,7 @@ class RemoteDeathWatchSpec extends AkkaSpec(RemoteDeathWatchSpec.config) with Im
     expectMsg(60.seconds, path)
   }
 
-  // FIXME this is failing with Artery
-  "receive ActorIdentity(None) when identified node is unknown host" ignore {
+  "receive ActorIdentity(None) when identified node is unknown host" in {
     val path = RootActorPath(Address("artery", system.name, "unknownhost2", 2552)) / "user" / "subject"
     system.actorSelection(path) ! Identify(path)
     expectMsg(60.seconds, ActorIdentity(path, None))
diff --git a/akka-remote/src/test/scala/akka/remote/artery/SystemMessageDeliverySpec.scala b/akka-remote/src/test/scala/akka/remote/artery/SystemMessageDeliverySpec.scala
index a84c964338..5f9a3e0b50 100644
--- a/akka-remote/src/test/scala/akka/remote/artery/SystemMessageDeliverySpec.scala
+++ b/akka-remote/src/test/scala/akka/remote/artery/SystemMessageDeliverySpec.scala
@@ -66,9 +66,10 @@ class SystemMessageDeliverySpec extends AkkaSpec(SystemMessageDeliverySpec.confi
 
   private def send(sendCount: Int, resendInterval: FiniteDuration, outboundContext: OutboundContext): Source[Send, NotUsed] = {
     val remoteRef = null.asInstanceOf[RemoteActorRef] // not used
+    val deadLetters = TestProbe().ref
     Source(1 to sendCount)
       .map(n ⇒ Send("msg-" + n, OptionVal.None, remoteRef, None))
-      .via(new SystemMessageDelivery(outboundContext, resendInterval, maxBufferSize = 1000))
+      .via(new SystemMessageDelivery(outboundContext, deadLetters, resendInterval, maxBufferSize = 1000))
   }
 
   private def inbound(inboundContext: InboundContext): Flow[Send, InboundEnvelope, NotUsed] = {