diff --git a/src/Microsoft.Net.Http.Server/NativeInterop/UnsafeNativeMethods.cs b/src/Microsoft.Net.Http.Server/NativeInterop/UnsafeNativeMethods.cs
index cac47b387d..3d005ba6b7 100644
--- a/src/Microsoft.Net.Http.Server/NativeInterop/UnsafeNativeMethods.cs
+++ b/src/Microsoft.Net.Http.Server/NativeInterop/UnsafeNativeMethods.cs
@@ -193,7 +193,7 @@ namespace Microsoft.Net.Http.Server
             internal static extern uint HttpSendResponseEntityBody2(SafeHandle requestQueueHandle, ulong requestId, uint flags, ushort entityChunkCount, IntPtr pEntityChunks, out uint pBytesSent, SafeLocalFree pRequestBuffer, uint requestBufferLength, SafeHandle pOverlapped, IntPtr pLogData);
 
             [DllImport(HTTPAPI, ExactSpelling = true, CallingConvention = CallingConvention.StdCall, SetLastError = true)]
-            internal static extern uint HttpWaitForDisconnect(SafeHandle requestQueueHandle, ulong connectionId, SafeNativeOverlapped pOverlapped);
+            internal static extern uint HttpWaitForDisconnectEx(SafeHandle requestQueueHandle, ulong connectionId, uint reserved, SafeNativeOverlapped overlapped);
 
             [DllImport(HTTPAPI, ExactSpelling = true, CallingConvention = CallingConvention.StdCall, SetLastError = true)]
             internal static extern uint HttpCreateServerSession(HTTPAPI_VERSION version, ulong* serverSessionId, uint reserved);
diff --git a/src/Microsoft.Net.Http.Server/WebListener.cs b/src/Microsoft.Net.Http.Server/WebListener.cs
index d68eceb01d..e897f05e42 100644
--- a/src/Microsoft.Net.Http.Server/WebListener.cs
+++ b/src/Microsoft.Net.Http.Server/WebListener.cs
@@ -768,7 +768,7 @@ namespace Microsoft.Net.Http.Server
             uint statusCode;
             try
             {
-                statusCode = UnsafeNclNativeMethods.HttpApi.HttpWaitForDisconnect(_requestQueueHandle, connectionId, nativeOverlapped);
+                statusCode = UnsafeNclNativeMethods.HttpApi.HttpWaitForDisconnectEx(_requestQueueHandle, connectionId, 0, nativeOverlapped);
             }
             catch (Win32Exception exception)
             {
diff --git a/test/Microsoft.Net.Http.Server.FunctionalTests/ServerTests.cs b/test/Microsoft.Net.Http.Server.FunctionalTests/ServerTests.cs
index 23c641dea3..f4abdb333d 100644
--- a/test/Microsoft.Net.Http.Server.FunctionalTests/ServerTests.cs
+++ b/test/Microsoft.Net.Http.Server.FunctionalTests/ServerTests.cs
@@ -81,24 +81,25 @@ namespace Microsoft.Net.Http.Server
             string address;
             using (var server = Utilities.CreateHttpServer(out address))
             {
-                // Note: System.Net.Sockets does not RST the connection by default, it just FINs.
-                // Http.Sys's disconnect notice requires a RST.
-                Task<Socket> responseTask = SendHungRequestAsync("GET", address);
-
-                var context = await server.GetContextAsync();
-                CancellationToken ct = context.DisconnectToken;
-                Assert.True(ct.CanBeCanceled, "CanBeCanceled");
-                Assert.False(ct.IsCancellationRequested, "IsCancellationRequested");
-                ct.Register(() => canceled.Set());
-
-                using (Socket socket = await responseTask)
+                using (var client = new HttpClient())
                 {
-                    socket.Close(0); // Force a RST
-                }
-                Assert.True(canceled.WaitOne(interval), "canceled");
-                Assert.True(ct.IsCancellationRequested, "IsCancellationRequested");
+                    Task<HttpResponseMessage> responseTask = client.GetAsync(address);
 
-                context.Dispose();
+                    var context = await server.GetContextAsync();
+                    CancellationToken ct = context.DisconnectToken;
+                    Assert.True(ct.CanBeCanceled, "CanBeCanceled");
+                    Assert.False(ct.IsCancellationRequested, "IsCancellationRequested");
+                    ct.Register(() => canceled.Set());
+
+                    client.CancelPendingRequests();
+
+                    Assert.True(canceled.WaitOne(interval), "canceled");
+                    Assert.True(ct.IsCancellationRequested, "IsCancellationRequested");
+
+                    await Assert.ThrowsAsync<TaskCanceledException>(() => responseTask);
+
+                    context.Dispose();
+                }
             }
         }
 
@@ -111,9 +112,7 @@ namespace Microsoft.Net.Http.Server
             string address;
             using (var server = Utilities.CreateHttpServer(out address))
             {
-                // Note: System.Net.Sockets does not RST the connection by default, it just FINs.
-                // Http.Sys's disconnect notice requires a RST.
-                Task<Socket> responseTask = SendHungRequestAsync("GET", address);
+                var responseTask = SendRequestAsync(address);
 
                 var context = await server.GetContextAsync();
                 CancellationToken ct = context.DisconnectToken;
@@ -124,10 +123,44 @@ namespace Microsoft.Net.Http.Server
                 Assert.True(canceled.WaitOne(interval), "Aborted");
                 Assert.True(ct.IsCancellationRequested, "IsCancellationRequested");
 
-                using (Socket socket = await responseTask)
+                // HttpClient re-tries the request because it doesn't know if the request was received.
+                context = await server.GetContextAsync();
+                context.Abort();
+
+                await Assert.ThrowsAsync<HttpRequestException>(() => responseTask);
+            }
+        }
+
+        [Fact]
+        public async Task Server_ConnectionCloseHeader_CancellationTokenFires()
+        {
+            TimeSpan interval = TimeSpan.FromSeconds(1);
+            ManualResetEvent canceled = new ManualResetEvent(false);
+
+            string address;
+            using (var server = Utilities.CreateHttpServer(out address))
+            {
+                Task<string> responseTask = SendRequestAsync(address);
+
+                var context = await server.GetContextAsync();
+                CancellationToken ct = context.DisconnectToken;
+                Assert.True(ct.CanBeCanceled, "CanBeCanceled");
+                Assert.False(ct.IsCancellationRequested, "IsCancellationRequested");
+                ct.Register(() => canceled.Set());
+
+                context.Response.Headers["Connection"] = "close";
+
+                context.Response.ContentLength = 11;
+                using (var writer = new StreamWriter(context.Response.Body))
                 {
-                    Assert.Throws<SocketException>(() => socket.Receive(new byte[10]));
+                    writer.Write("Hello World");
                 }
+
+                Assert.True(canceled.WaitOne(interval), "Disconnected");
+                Assert.True(ct.IsCancellationRequested, "IsCancellationRequested");
+
+                string response = await responseTask;
+                Assert.Equal("Hello World", response);
             }
         }
 
@@ -166,48 +199,5 @@ namespace Microsoft.Net.Http.Server
                 return await response.Content.ReadAsStringAsync();
             }
         }
-
-        private async Task<Socket> SendHungRequestAsync(string method, string address)
-        {
-            // Connect with a socket
-            Uri uri = new Uri(address);
-            TcpClient client = new TcpClient();
-            try
-            {
-                await client.ConnectAsync(uri.Host, uri.Port);
-                NetworkStream stream = client.GetStream();
-
-                // Send an HTTP GET request
-                byte[] requestBytes = BuildGetRequest(method, uri);
-                await stream.WriteAsync(requestBytes, 0, requestBytes.Length);
-                
-                // Return the opaque network stream
-                return client.Client;
-            }
-            catch (Exception)
-            {
-                client.Close();
-                throw;
-            }
-        }
-
-        private byte[] BuildGetRequest(string method, Uri uri)
-        {
-            StringBuilder builder = new StringBuilder();
-            builder.Append(method);
-            builder.Append(" ");
-            builder.Append(uri.PathAndQuery);
-            builder.Append(" HTTP/1.1");
-            builder.AppendLine();
-
-            builder.Append("Host: ");
-            builder.Append(uri.Host);
-            builder.Append(':');
-            builder.Append(uri.Port);
-            builder.AppendLine();
-
-            builder.AppendLine();
-            return Encoding.ASCII.GetBytes(builder.ToString());
-        }
     }
 }