diff --git a/src/Microsoft.AspNetCore.Sockets.Client.Http/WebSocketsTransport.cs b/src/Microsoft.AspNetCore.Sockets.Client.Http/WebSocketsTransport.cs
index 5f7345162f..7177993346 100644
--- a/src/Microsoft.AspNetCore.Sockets.Client.Http/WebSocketsTransport.cs
+++ b/src/Microsoft.AspNetCore.Sockets.Client.Http/WebSocketsTransport.cs
@@ -67,6 +67,7 @@ namespace Microsoft.AspNetCore.Sockets.Client
             // https://github.com/SignalR/SignalR/blob/1fba14fa3437e24c204dfaf8a18db3fce8acad3c/src/Microsoft.AspNet.SignalR.Core/Owin/WebSockets/WebSocketHandler.cs#L248-L251
             Running = Task.WhenAll(sendTask, receiveTask).ContinueWith(t =>
             {
+                _webSocket.Dispose();
                 _logger.TransportStopped(_connectionId, t.Exception?.InnerException);
                _application.Out.TryComplete(t.IsFaulted ? t.Exception.InnerException : null);
                return t;
@@ -221,7 +222,6 @@ namespace Microsoft.AspNetCore.Sockets.Client
             _logger.TransportStopping(_connectionId);
 
             await CloseWebSocket();
-            _webSocket.Dispose();
 
             try
             {
@@ -242,7 +242,13 @@ namespace Microsoft.AspNetCore.Sockets.Client
                 if (_webSocket.State != WebSocketState.Closed)
                 {
                     _logger.ClosingWebSocket(_connectionId);
-                    await _webSocket.CloseAsync(WebSocketCloseStatus.NormalClosure, null, CancellationToken.None);
+
+                    // We intentionally don't pass _transportCts.Token to CloseOutputAsync. The token can be cancelled
+                    // for reasons not related to webSocket in which case we would not close the websocket gracefully.
+                    await _webSocket.CloseOutputAsync(WebSocketCloseStatus.NormalClosure, null, CancellationToken.None);
+
+                    // shutdown the transport after a timeout in case the server does not send close frame
+                    _transportCts.CancelAfter(TimeSpan.FromSeconds(5));
                 }
             }
             catch (Exception ex)
diff --git a/test/Microsoft.AspNetCore.SignalR.Tests/EndToEndTests.cs b/test/Microsoft.AspNetCore.SignalR.Tests/EndToEndTests.cs
index b67b3d1442..004653180b 100644
--- a/test/Microsoft.AspNetCore.SignalR.Tests/EndToEndTests.cs
+++ b/test/Microsoft.AspNetCore.SignalR.Tests/EndToEndTests.cs
@@ -42,6 +42,17 @@ namespace Microsoft.AspNetCore.SignalR.Tests
             _serverFixture = serverFixture;
         }
 
+        [Fact]
+        public async Task CanStartConnectionUsingDefaultTransport()
+        {
+            var url = _serverFixture.BaseUrl + "/echo";
+            // The test should connect to the server using WebSockets transport on Windows 8 and newer.
+            // On Windows 7/2008R2 it should use ServerSentEvents transport to connect to the server.
+            var connection = new HttpConnection(new Uri(url));
+            await connection.StartAsync().OrTimeout();
+            await connection.DisposeAsync().OrTimeout();
+        }
+
         [ConditionalFact]
         [OSSkipCondition(OperatingSystems.Windows, WindowsVersions.Win7, WindowsVersions.Win2008R2, SkipReason = "No WebSockets Client for this platform")]
         public async Task WebSocketsTest()