diff --git a/src/SignalR/clients/java/signalr/core/src/main/java/com/microsoft/signalr/HubConnection.java b/src/SignalR/clients/java/signalr/core/src/main/java/com/microsoft/signalr/HubConnection.java
index 0aa4e4c336..e67bdacc88 100644
--- a/src/SignalR/clients/java/signalr/core/src/main/java/com/microsoft/signalr/HubConnection.java
+++ b/src/SignalR/clients/java/signalr/core/src/main/java/com/microsoft/signalr/HubConnection.java
@@ -527,7 +527,9 @@ public class HubConnection implements AutoCloseable {
             hubConnectionStateLock.unlock();
         }
 
-        return transport.stop();
+        Completable stop = transport.stop();
+        stop.onErrorComplete().subscribe();
+        return stop;
     }
 
     /**
diff --git a/src/SignalR/clients/java/signalr/core/src/main/java/com/microsoft/signalr/LongPollingTransport.java b/src/SignalR/clients/java/signalr/core/src/main/java/com/microsoft/signalr/LongPollingTransport.java
index 00dc46f97b..d52d5edb38 100644
--- a/src/SignalR/clients/java/signalr/core/src/main/java/com/microsoft/signalr/LongPollingTransport.java
+++ b/src/SignalR/clients/java/signalr/core/src/main/java/com/microsoft/signalr/LongPollingTransport.java
@@ -19,7 +19,7 @@ import io.reactivex.subjects.CompletableSubject;
 
 class LongPollingTransport implements Transport {
     private OnReceiveCallBack onReceiveCallBack;
-    private TransportOnClosedCallback onClose;
+    private TransportOnClosedCallback onClose = (reason) -> {};
     private String url;
     private final HttpClient client;
     private final HttpClient pollingClient;
@@ -30,6 +30,7 @@ class LongPollingTransport implements Transport {
     private String pollUrl;
     private String closeError;
     private CompletableSubject receiveLoop = CompletableSubject.create();
+    private CompletableSubject closeSubject = CompletableSubject.create();
     private ExecutorService threadPool;
     private ExecutorService onReceiveThread;
     private AtomicBoolean stopCalled = new AtomicBoolean(false);
@@ -157,7 +158,7 @@ class LongPollingTransport implements Transport {
     public Completable stop() {
         if (stopCalled.compareAndSet(false, true)) {
             this.active = false;
-            return this.updateHeaderToken().andThen(Completable.defer(() -> {
+            Completable stopCompletable = this.updateHeaderToken().andThen(Completable.defer(() -> {
                 HttpRequest request = new HttpRequest();
                 request.addHeaders(headers);
                 return this.pollingClient.delete(this.url, request).ignoreElement()
@@ -168,8 +169,10 @@ class LongPollingTransport implements Transport {
             })).doOnError(e -> {
                 cleanup(e.getMessage());
             });
+
+            stopCompletable.subscribe(closeSubject);
         }
-        return Completable.complete();
+        return closeSubject;
     }
 
     private void cleanup(String error) {
diff --git a/src/SignalR/clients/java/signalr/test/src/main/java/com/microsoft/signalr/HubConnectionTest.java b/src/SignalR/clients/java/signalr/test/src/main/java/com/microsoft/signalr/HubConnectionTest.java
index 402a21c74b..57c0c8c9b3 100644
--- a/src/SignalR/clients/java/signalr/test/src/main/java/com/microsoft/signalr/HubConnectionTest.java
+++ b/src/SignalR/clients/java/signalr/test/src/main/java/com/microsoft/signalr/HubConnectionTest.java
@@ -3127,6 +3127,84 @@ class HubConnectionTest {
         assertEquals(HubConnectionState.DISCONNECTED, hubConnection.getConnectionState());
     }
 
+    @Test
+    public void stopWithoutObservingWithLongPollingTransportStops() {
+        AtomicInteger requestCount = new AtomicInteger(0);
+        CompletableSubject blockGet = CompletableSubject.create();
+        TestHttpClient client = new TestHttpClient()
+            .on("POST", "http://example.com/negotiate?negotiateVersion=1",
+                (req) -> Single.just(new HttpResponse(200, "",
+                        TestUtils.stringToByteBuffer("{\"connectionId\":\"bVOiRPG8-6YiJ6d7ZcTOVQ\",\""
+                                + "availableTransports\":[{\"transport\":\"LongPolling\",\"transferFormats\":[\"Text\",\"Binary\"]}]}"))))
+            .on("GET", (req) -> {
+                if (requestCount.getAndIncrement() > 1) {
+                    blockGet.blockingAwait();
+                }
+                return Single.just(new HttpResponse(200, "", TestUtils.stringToByteBuffer("{}" + RECORD_SEPARATOR)));
+            })
+            .on("POST", "http://example.com?id=bVOiRPG8-6YiJ6d7ZcTOVQ", (req) -> {
+                return Single.just(new HttpResponse(200, "", TestUtils.stringToByteBuffer("")));
+            });
+
+        HubConnection hubConnection = HubConnectionBuilder
+                .create("http://example.com")
+                .withTransport(TransportEnum.LONG_POLLING)
+                .withHttpClient(client)
+                .build();
+
+        CompletableSubject closed = CompletableSubject.create();
+        hubConnection.onClosed((e) -> {
+            closed.onComplete();
+        });
+
+        hubConnection.start().timeout(1, TimeUnit.SECONDS).blockingAwait();
+
+        hubConnection.stop();
+        closed.timeout(1, TimeUnit.SECONDS).blockingAwait();
+        blockGet.onComplete();
+        assertEquals(HubConnectionState.DISCONNECTED, hubConnection.getConnectionState());
+    }
+
+    @Test
+    public void hubConnectionClosesAndRunsOnClosedCallbackAfterCloseMessageWithLongPolling()  {
+        AtomicInteger requestCount = new AtomicInteger(0);
+        CompletableSubject blockGet = CompletableSubject.create();
+        TestHttpClient client = new TestHttpClient()
+            .on("POST", "http://example.com/negotiate?negotiateVersion=1",
+                (req) -> Single.just(new HttpResponse(200, "",
+                        TestUtils.stringToByteBuffer("{\"connectionId\":\"bVOiRPG8-6YiJ6d7ZcTOVQ\",\""
+                                + "availableTransports\":[{\"transport\":\"LongPolling\",\"transferFormats\":[\"Text\",\"Binary\"]}]}"))))
+            .on("GET", (req) -> {
+                if (requestCount.getAndIncrement() > 1) {
+                    blockGet.blockingAwait();
+                    return Single.just(new HttpResponse(200, "", TestUtils.stringToByteBuffer("{\"type\":7}" + RECORD_SEPARATOR)));
+                }
+                return Single.just(new HttpResponse(200, "", TestUtils.stringToByteBuffer("{}" + RECORD_SEPARATOR)));
+            })
+            .on("POST", "http://example.com?id=bVOiRPG8-6YiJ6d7ZcTOVQ", (req) -> {
+                return Single.just(new HttpResponse(200, "", TestUtils.stringToByteBuffer("")));
+            });
+
+        HubConnection hubConnection = HubConnectionBuilder
+            .create("http://example.com")
+            .withTransport(TransportEnum.LONG_POLLING)
+            .withHttpClient(client)
+            .build();
+
+        CompletableSubject closed = CompletableSubject.create();
+        hubConnection.onClosed((ex) -> {
+            closed.onComplete();
+        });
+        hubConnection.start().timeout(1, TimeUnit.SECONDS).blockingAwait();
+
+        assertEquals(HubConnectionState.CONNECTED, hubConnection.getConnectionState());
+        blockGet.onComplete();
+
+        closed.timeout(1, TimeUnit.SECONDS).blockingAwait();
+
+        assertEquals(HubConnectionState.DISCONNECTED, hubConnection.getConnectionState());
+    }
+
     @Test
     public void receivingServerSentEventsTransportFromNegotiateFails() {
         TestHttpClient client = new TestHttpClient().on("POST", "http://example.com/negotiate?negotiateVersion=1",
diff --git a/src/SignalR/clients/java/signalr/test/src/main/java/com/microsoft/signalr/LongPollingTransportTest.java b/src/SignalR/clients/java/signalr/test/src/main/java/com/microsoft/signalr/LongPollingTransportTest.java
index 0e65390d39..6ee518d415 100644
--- a/src/SignalR/clients/java/signalr/test/src/main/java/com/microsoft/signalr/LongPollingTransportTest.java
+++ b/src/SignalR/clients/java/signalr/test/src/main/java/com/microsoft/signalr/LongPollingTransportTest.java
@@ -307,7 +307,7 @@ public class LongPollingTransportTest {
     }
 
     @Test
-    public void After204StopDoesNotTriggerOnClose() {
+    public void After204StopDoesNotTriggerOnCloseAgain() {
         AtomicBoolean firstPoll = new AtomicBoolean(true);
         CompletableSubject block = CompletableSubject.create();
         TestHttpClient client = new TestHttpClient()
@@ -317,6 +317,9 @@ public class LongPollingTransportTest {
                         return Single.just(new HttpResponse(200, "", TestUtils.emptyByteBuffer));
                     }
                     return Single.just(new HttpResponse(204, "", TestUtils.emptyByteBuffer));
+                })
+                .on("DELETE", (req) -> {
+                    return Single.just(new HttpResponse(200, "", TestUtils.emptyByteBuffer));
                 });
 
         Map<String, String> headers = new HashMap<>();
@@ -356,7 +359,7 @@ public class LongPollingTransportTest {
                 })
                 .on("DELETE", (req) ->{
                     //Unblock the last poll when we sent the DELETE request.
-                   block.onComplete();
+                    block.onComplete();
                     return Single.just(new HttpResponse(200, "", TestUtils.emptyByteBuffer));
                 });
 
@@ -373,4 +376,25 @@ public class LongPollingTransportTest {
         assertEquals(1, onCloseCount.get());
         assertFalse(transport.isActive());
     }
+
+    @Test
+    public void ErrorFromClosePropagatesOnSecondStopCall() {
+        AtomicBoolean firstPoll = new AtomicBoolean(true);
+        TestHttpClient client = new TestHttpClient()
+                .on("GET", (req) -> {
+                    if (firstPoll.get()) {
+                        firstPoll.set(false);
+                        return Single.just(new HttpResponse(200, "", TestUtils.emptyByteBuffer));
+                    }
+                    return Single.just(new HttpResponse(204, "", TestUtils.emptyByteBuffer));
+                });
+
+        Map<String, String> headers = new HashMap<>();
+        LongPollingTransport transport = new LongPollingTransport(headers, client, Single.just(""));
+
+        transport.start("http://example.com").timeout(100, TimeUnit.SECONDS).blockingAwait();
+
+        RuntimeException exception = assertThrows(RuntimeException.class, () -> transport.stop().blockingAwait(100, TimeUnit.SECONDS));
+        assertEquals("Request has no handler: DELETE http://example.com", exception.getMessage());
+    }
 }