diff --git a/akka-cluster-tools/src/main/scala/akka/cluster/singleton/ClusterSingletonManager.scala b/akka-cluster-tools/src/main/scala/akka/cluster/singleton/ClusterSingletonManager.scala
index 848a91bc92..5b65df3317 100644
--- a/akka-cluster-tools/src/main/scala/akka/cluster/singleton/ClusterSingletonManager.scala
+++ b/akka-cluster-tools/src/main/scala/akka/cluster/singleton/ClusterSingletonManager.scala
@@ -182,6 +182,7 @@ object ClusterSingletonManager {
     case object WasOldest extends State
     case object HandingOver extends State
     case object TakeOver extends State
+    case object Stopping extends State
     case object End extends State
 
     case object Uninitialized extends Data
@@ -191,6 +192,7 @@ object ClusterSingletonManager {
     final case class WasOldestData(singleton: ActorRef, singletonTerminated: Boolean,
                                    newOldestOption: Option[UniqueAddress]) extends Data
     final case class HandingOverData(singleton: ActorRef, handOverTo: Option[ActorRef]) extends Data
+    final case class StoppingData(singleton: ActorRef) extends Data
     case object EndData extends Data
     final case class DelayedMemberRemoved(member: Member)
 
@@ -631,15 +633,16 @@ class ClusterSingletonManager(
   }
 
   when(WasOldest) {
-    case Event(TakeOverRetry(count), WasOldestData(_, _, newOldestOption)) ⇒
-      if (count <= maxTakeOverRetries) {
+    case Event(TakeOverRetry(count), WasOldestData(singleton, singletonTerminated, newOldestOption)) ⇒
+      if (cluster.isTerminated && (newOldestOption.isEmpty || count > maxTakeOverRetries)) {
+        if (singletonTerminated) stop()
+        else gotoStopping(singleton)
+      } else if (count <= maxTakeOverRetries) {
         logInfo("Retry [{}], sending TakeOverFromMe to [{}]", count, newOldestOption.map(_.address))
         newOldestOption.foreach(node ⇒ peer(node.address) ! TakeOverFromMe)
         setTimer(TakeOverRetryTimer, TakeOverRetry(count + 1), handOverRetryInterval, repeat = false)
         stay
-      } else if (cluster.isTerminated)
-        stop()
-      else
+      } else
         throw new ClusterSingletonManagerIsStuck(s"Expected hand-over to [${newOldestOption}] never occured")
 
     case Event(HandOverToMe, WasOldestData(singleton, singletonTerminated, _)) ⇒
@@ -692,6 +695,16 @@ class ClusterSingletonManager(
       goto(End) using EndData
   }
 
+  def gotoStopping(singleton: ActorRef): State = {
+    singleton ! terminationMessage
+    goto(Stopping) using StoppingData(singleton)
+  }
+
+  when(Stopping) {
+    case (Event(Terminated(ref), StoppingData(singleton))) if ref == singleton ⇒
+      stop()
+  }
+
   when(End) {
     case Event(MemberRemoved(m, _), _) if m.uniqueAddress == cluster.selfUniqueAddress ⇒
       logInfo("Self removed, stopping ClusterSingletonManager")
diff --git a/akka-cluster-tools/src/multi-jvm/scala/akka/cluster/singleton/ClusterSingletonManagerLeaveSpec.scala b/akka-cluster-tools/src/multi-jvm/scala/akka/cluster/singleton/ClusterSingletonManagerLeaveSpec.scala
index b66fe09871..5bbad79e82 100644
--- a/akka-cluster-tools/src/multi-jvm/scala/akka/cluster/singleton/ClusterSingletonManagerLeaveSpec.scala
+++ b/akka-cluster-tools/src/multi-jvm/scala/akka/cluster/singleton/ClusterSingletonManagerLeaveSpec.scala
@@ -45,11 +45,17 @@ object ClusterSingletonManagerLeaveSpec extends MultiNodeConfig {
    * The singleton actor
    */
   class Echo(testActor: ActorRef) extends Actor {
+    override def preStart(): Unit = {
+      testActor ! "preStart"
+    }
     override def postStop(): Unit = {
-      testActor ! "stopped"
+      testActor ! "postStop"
     }
 
     def receive = {
+      case "stop" ⇒
+        testActor ! "stop"
+        context.stop(self)
       case _ ⇒
         sender() ! self
     }
@@ -78,7 +84,7 @@ class ClusterSingletonManagerLeaveSpec extends MultiNodeSpec(ClusterSingletonMan
     system.actorOf(
       ClusterSingletonManager.props(
         singletonProps = Props(classOf[Echo], testActor),
-        terminationMessage = PoisonPill,
+        terminationMessage = "stop",
         settings = ClusterSingletonManagerSettings(system)),
       name = "echo")
   }
@@ -97,12 +103,22 @@ class ClusterSingletonManagerLeaveSpec extends MultiNodeSpec(ClusterSingletonMan
       join(first, first)
 
       runOn(first) {
-        echoProxy ! "hello"
-        expectMsgType[ActorRef](5.seconds)
+        within(5.seconds) {
+          expectMsg("preStart")
+          echoProxy ! "hello"
+          expectMsgType[ActorRef]
+        }
       }
       enterBarrier("first-active")
 
       join(second, first)
+      runOn(first, second) {
+        within(10.seconds) {
+          awaitAssert(cluster.state.members.count(m ⇒ m.status == MemberStatus.Up) should be(2))
+        }
+      }
+      enterBarrier("second-up")
+
       join(third, first)
       within(10.seconds) {
         awaitAssert(cluster.state.members.count(m ⇒ m.status == MemberStatus.Up) should be(3))
@@ -114,14 +130,20 @@ class ClusterSingletonManagerLeaveSpec extends MultiNodeSpec(ClusterSingletonMan
       }
 
       runOn(first) {
-        expectMsg(10.seconds, "stopped")
+        expectMsg(10.seconds, "stop")
+        expectMsg("postStop")
       }
       enterBarrier("first-stopped")
 
+      runOn(second) {
+        expectMsg("preStart")
+      }
+      enterBarrier("second-started")
+
       runOn(second, third) {
         val p = TestProbe()
         val firstAddress = node(first).address
-        p.within(10.seconds) {
+        p.within(15.seconds) {
           p.awaitAssert {
             echoProxy.tell("hello2", p.ref)
             p.expectMsgType[ActorRef](1.seconds).path.address should not be (firstAddress)
@@ -129,8 +151,33 @@ class ClusterSingletonManagerLeaveSpec extends MultiNodeSpec(ClusterSingletonMan
           }
         }
       }
+      enterBarrier("second-working")
+
+      runOn(third) {
+        cluster.leave(node(second).address)
+      }
+
+      runOn(second) {
+        expectMsg(15.seconds, "stop")
+        expectMsg("postStop")
+      }
+      enterBarrier("second-stopped")
+
+      runOn(third) {
+        expectMsg("preStart")
+      }
+      enterBarrier("third-started")
+
+      runOn(third) {
+        cluster.leave(node(third).address)
+      }
+
+      runOn(third) {
+        expectMsg(5.seconds, "stop")
+        expectMsg("postStop")
+      }
+      enterBarrier("third-stopped")
 
-      enterBarrier("hand-over-done")
     }
 
   }