diff --git a/akka-remote/src/main/resources/reference.conf b/akka-remote/src/main/resources/reference.conf
index ac9aae541a..51c6b4214d 100644
--- a/akka-remote/src/main/resources/reference.conf
+++ b/akka-remote/src/main/resources/reference.conf
@@ -272,6 +272,14 @@ akka {
     # resent.
     resend-interval = 2 s
 
+    # WARNING: this setting should not be not changed unless all of its consequences
+    # are properly understood which assumes experience with remoting internals
+    # or expert advice.
+    # This setting defines the time after redelivery attempts of internal management
+    # signals are stopped to a remote system that has been not confirmed to be alive by
+    # this system before.
+    initial-system-message-delivery-timeout = 3 m
+
     ### Transports and adapters
 
     # List of the transport drivers that will be loaded by the remoting.
diff --git a/akka-remote/src/main/scala/akka/remote/Endpoint.scala b/akka-remote/src/main/scala/akka/remote/Endpoint.scala
index 90a5c240ed..8a43138a74 100644
--- a/akka-remote/src/main/scala/akka/remote/Endpoint.scala
+++ b/akka-remote/src/main/scala/akka/remote/Endpoint.scala
@@ -241,6 +241,7 @@ private[remote] class ReliableDeliverySupervisor(
 
   var writer: ActorRef = createWriter()
   var uid: Option[Int] = handleOrActive map { _.handshakeInfo.uid }
+  val bailoutAt: Deadline = Deadline.now + settings.InitialSysMsgDeliveryTimeout
   // Processing of Acks has to be delayed until the UID after a reconnect is discovered. Depending whether the
   // UID matches the expected one, pending Acks can be processed, or must be dropped. It is guaranteed that for
   // any inbound connections (calling createWriter()) the first message from that connection is GotUid() therefore
@@ -321,6 +322,14 @@ private[remote] class ReliableDeliverySupervisor(
       context.system.scheduler.scheduleOnce(settings.RetryGateClosedFor, self, Ungate)
     case Ungate ⇒
       if (resendBuffer.nonAcked.nonEmpty || resendBuffer.nacked.nonEmpty) {
+        // If we talk to a system we have not talked to before (or has given up talking to in the past) stop
+        // system delivery attempts after the specified time. This act will drop the pending system messages and gate the
+        // remote address at the EndpointManager level stopping this actor. In case the remote system becomes reachable
+        // again it will be immediately quarantined due to out-of-sync system message buffer and becomes quarantined.
+        // In other words, this action is safe.
+        if (!uidConfirmed && bailoutAt.isOverdue())
+          throw new InvalidAssociation(localAddress, remoteAddress,
+            new java.util.concurrent.TimeoutException("Delivery of system messages timed out and they were dropped."))
         writer = createWriter()
         // Resending will be triggered by the incoming GotUid message after the connection finished
         context.become(receive)
diff --git a/akka-remote/src/main/scala/akka/remote/RemoteSettings.scala b/akka-remote/src/main/scala/akka/remote/RemoteSettings.scala
index bdf2e6c836..930a8ebb2d 100644
--- a/akka-remote/src/main/scala/akka/remote/RemoteSettings.scala
+++ b/akka-remote/src/main/scala/akka/remote/RemoteSettings.scala
@@ -78,6 +78,10 @@ final class RemoteSettings(val config: Config) {
     getInt("akka.remote.system-message-buffer-size")
   } requiring (_ > 0, "system-message-buffer-size must be > 0")
 
+  val InitialSysMsgDeliveryTimeout: FiniteDuration = {
+    config.getMillisDuration("akka.remote.initial-system-message-delivery-timeout")
+  } requiring (_ > Duration.Zero, "initial-system-message-delivery-timeout must be > 0")
+
   val QuarantineDuration: FiniteDuration = {
     config.getMillisDuration("akka.remote.prune-quarantine-marker-after").requiring(_ > Duration.Zero,
       "prune-quarantine-marker-after must be > 0 ms")
diff --git a/akka-remote/src/test/scala/akka/remote/RemoteConfigSpec.scala b/akka-remote/src/test/scala/akka/remote/RemoteConfigSpec.scala
index 27ec6a2001..f1b458c6b8 100644
--- a/akka-remote/src/test/scala/akka/remote/RemoteConfigSpec.scala
+++ b/akka-remote/src/test/scala/akka/remote/RemoteConfigSpec.scala
@@ -40,6 +40,7 @@ class RemoteConfigSpec extends AkkaSpec(
       SysMsgAckTimeout should be(0.3 seconds)
       SysResendTimeout should be(2 seconds)
       SysMsgBufferSize should be(1000)
+      InitialSysMsgDeliveryTimeout should be(3 minutes)
       QuarantineDuration should be(5 days)
       CommandAckTimeout.duration should be(30 seconds)
       Transports.size should be(1)
diff --git a/akka-remote/src/test/scala/akka/remote/RemoteDeathWatchSpec.scala b/akka-remote/src/test/scala/akka/remote/RemoteDeathWatchSpec.scala
index bfa1072f72..ed4beec3ac 100644
--- a/akka-remote/src/test/scala/akka/remote/RemoteDeathWatchSpec.scala
+++ b/akka-remote/src/test/scala/akka/remote/RemoteDeathWatchSpec.scala
@@ -20,6 +20,8 @@ akka {
             /watchers.remote = "akka.tcp://other@localhost:2666"
         }
     }
+    remote.retry-gate-closed-for = 1 s
+    remote.initial-system-message-delivery-timeout = 3 s
     remote.netty.tcp {
         hostname = "localhost"
         port = 0
@@ -44,7 +46,7 @@ akka {
   "receive Terminated when system of de-serialized ActorRef is not running" in {
     val probe = TestProbe()
     system.eventStream.subscribe(probe.ref, classOf[QuarantinedEvent])
-    val rarp = system.asInstanceOf[ExtendedActorSystem].provider.asInstanceOf[RemoteActorRefProvider]
+    val rarp = RARP(system).provider
     // pick an unused port
     val port = TestUtils.temporaryServerAddress().getPort
     // simulate de-serialized ActorRef
@@ -83,4 +85,21 @@ akka {
     expectMsg(60.seconds, ActorIdentity(path, None))
   }
 
+  "quarantine systems after unsuccessful system message delivery if have not communicated before" in {
+    // Synthesize an ActorRef to a remote system this one has never talked to before.
+    // This forces ReliableDeliverySupervisor to start with unknown remote system UID.
+    val extinctPath = RootActorPath(Address("akka.tcp", "extinct-system", "localhost", TestUtils.temporaryServerAddress().getPort)) / "user" / "noone"
+    val transport = RARP(system).provider.transport
+    val extinctRef = new RemoteActorRef(transport, transport.localAddressForRemote(extinctPath.address),
+      extinctPath, Nobody, props = None, deploy = None)
+
+    val probe = TestProbe()
+    probe.watch(extinctRef)
+    probe.unwatch(extinctRef)
+
+    probe.expectNoMsg(5.seconds)
+    system.eventStream.subscribe(probe.ref, classOf[Warning])
+    probe.expectNoMsg(RARP(system).provider.remoteSettings.RetryGateClosedFor * 2)
+  }
+
 }