diff --git a/akka-remote/src/test/scala/akka/remote/classic/RemotingSpec.scala b/akka-remote/src/test/scala/akka/remote/classic/RemotingSpec.scala
index b0e1210a8f..80dc96e558 100644
--- a/akka-remote/src/test/scala/akka/remote/classic/RemotingSpec.scala
+++ b/akka-remote/src/test/scala/akka/remote/classic/RemotingSpec.scala
@@ -23,6 +23,8 @@ import com.typesafe.config._
 import scala.concurrent.{ Await, Future }
 import scala.concurrent.duration._
 
+import scala.util.control.NonFatal
+
 object RemotingSpec {
 
   final case class ActorSelReq(s: String)
@@ -532,7 +534,7 @@ class RemotingSpec extends AkkaSpec(RemotingSpec.cfg) with ImplicitSender with D
       }
     }
 
-    "should not publish AddressTerminated even on InvalidAssociationExecptions" in {
+    "should not publish AddressTerminated even on InvalidAssociationExceptions" in {
       val localAddress = Address("akka.test", "system1", "localhost", 1)
       val rawLocalAddress = localAddress.copy(protocol = "test")
       val remoteAddress = Address("akka.test", "system2", "localhost", 2)
@@ -754,33 +756,49 @@ class RemotingSpec extends AkkaSpec(RemotingSpec.cfg) with ImplicitSender with D
 
     }
 
+    // retry a few times as the temporaryServerAddress can be taken by the time the new actor system
+    // binds
+    def selectionAndBind(
+        config: Config,
+        thisSystem: ActorSystem,
+        probe: TestProbe,
+        retries: Int = 3): (ActorSystem, ActorSelection) = {
+      val otherAddress = temporaryServerAddress()
+      val otherConfig = ConfigFactory.parseString(s"""
+              akka.remote.classic.netty.tcp.port = ${otherAddress.getPort}
+              """).withFallback(config)
+      val otherSelection =
+        thisSystem.actorSelection(s"akka.tcp://other-system@localhost:${otherAddress.getPort}/user/echo")
+      otherSelection.tell("ping", probe.ref)
+      probe.expectNoMessage(200.millis)
+      try {
+        (ActorSystem("other-system", otherConfig), otherSelection)
+      } catch {
+        case NonFatal(ex) if ex.getMessage.contains("Failed to bind") && retries > 0 =>
+          selectionAndBind(config, thisSystem, probe, retries = retries - 1)
+        case other =>
+          throw other
+      }
+    }
+
     "be able to connect to system even if it's not there at first" in {
       val config = ConfigFactory.parseString(s"""
-            akka.remote.enabled-transports = ["akka.remote.classic.netty.tcp"]
+            akka.remote.classic.enabled-transports = ["akka.remote.classic.netty.tcp"]
             akka.remote.classic.netty.tcp.port = 0
-            akka.remote.retry-gate-closed-for = 5s
+            akka.remote.classic.retry-gate-closed-for = 5s
             """).withFallback(remoteSystem.settings.config)
       val thisSystem = ActorSystem("this-system", config)
       try {
         muteSystem(thisSystem)
         val probe = new TestProbe(thisSystem)
-        val probeSender = probe.ref
-        val otherAddress = temporaryServerAddress()
-        val otherConfig = ConfigFactory.parseString(s"""
-              akka.remote.classic.netty.tcp.port = ${otherAddress.getPort}
-              """).withFallback(config)
-        val otherSelection =
-          thisSystem.actorSelection(s"akka.tcp://other-system@localhost:${otherAddress.getPort}/user/echo")
-        otherSelection.tell("ping", probeSender)
-        probe.expectNoMessage(1.seconds)
-        val otherSystem = ActorSystem("other-system", otherConfig)
+        val (otherSystem, otherSelection) = selectionAndBind(config, thisSystem, probe)
         try {
           muteSystem(otherSystem)
           probe.expectNoMessage(2.seconds)
           otherSystem.actorOf(Props[Echo2], "echo")
           within(5.seconds) {
             awaitAssert {
-              otherSelection.tell("ping", probeSender)
+              otherSelection.tell("ping", probe.ref)
               assert(probe.expectMsgType[(String, ActorRef)](500.millis)._1 == "pong")
             }
           }
@@ -794,9 +812,9 @@ class RemotingSpec extends AkkaSpec(RemotingSpec.cfg) with ImplicitSender with D
 
     "allow other system to connect even if it's not there at first" in {
       val config = ConfigFactory.parseString(s"""
-            akka.remote.enabled-transports = ["akka.remote.classic.netty.tcp"]
+            akka.remote.classic.enabled-transports = ["akka.remote.classic.netty.tcp"]
             akka.remote.classic.netty.tcp.port = 0
-            akka.remote.retry-gate-closed-for = 5s
+            akka.remote.classic.retry-gate-closed-for = 5s
             """).withFallback(remoteSystem.settings.config)
       val thisSystem = ActorSystem("this-system", config)
       try {