diff --git a/src/Microsoft.AspNetCore.Server.HttpSys/HttpSysOptions.cs b/src/Microsoft.AspNetCore.Server.HttpSys/HttpSysOptions.cs
index 8b00e14e6a..85c8dcc2e1 100644
--- a/src/Microsoft.AspNetCore.Server.HttpSys/HttpSysOptions.cs
+++ b/src/Microsoft.AspNetCore.Server.HttpSys/HttpSysOptions.cs
@@ -79,12 +79,6 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             }
         }
 
-        /// <summary>
-        /// The amount of time to wait for active requests to drain while the server is shutting down.
-        /// New requests will receive a 503 response in this time period. The default is 5 seconds.
-        /// </summary>
-        public TimeSpan ShutdownTimeout { get; set; } = TimeSpan.FromSeconds(5);
-
         internal void SetRequestQueueLimit(RequestQueue requestQueue)
         {
             _requestQueue = requestQueue;
diff --git a/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs b/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs
index 01b8d831e8..e8aa2cca59 100644
--- a/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs
+++ b/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs
@@ -26,7 +26,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
 
         private bool _stopping;
         private int _outstandingRequests;
-        private ManualResetEvent _shutdownSignal;
+        private TaskCompletionSource<object> _shutdownSignal;
 
         private readonly ServerAddressesFeature _serverAddresses;
 
@@ -51,7 +51,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             _processRequest = new Action<object>(ProcessRequestAsync);
             _maxAccepts = _options.MaxAccepts;
             EnableResponseCaching = _options.EnableResponseCaching;
-            _shutdownSignal = new ManualResetEvent(false);
+            _shutdownSignal = new TaskCompletionSource<object>();
         }
 
         internal HttpSysListener Listener { get; }
@@ -60,7 +60,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
 
         public IFeatureCollection Features { get; }
 
-        public void Start<TContext>(IHttpApplication<TContext> application)
+        public Task StartAsync<TContext>(IHttpApplication<TContext> application, CancellationToken cancellationToken)
         {
             if (application == null)
             {
@@ -124,6 +124,8 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             Listener.Start();
 
             ActivateRequestProcessingLimits();
+
+            return Task.CompletedTask;
         }
 
         private void ActivateRequestProcessingLimits()
@@ -224,7 +226,8 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 {
                     if (Interlocked.Decrement(ref _outstandingRequests) == 0 && _stopping)
                     {
-                        _shutdownSignal.Set();
+                        LogHelper.LogInfo(_logger, "All requests drained.");
+                        _shutdownSignal.TrySetResult(0);
                     }
                 }
             }
@@ -242,24 +245,30 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             context.Dispose();
         }
 
-        public void Dispose()
+        public Task StopAsync(CancellationToken cancellationToken)
         {
             _stopping = true;
             // Wait for active requests to drain
             if (_outstandingRequests > 0)
             {
                 LogHelper.LogInfo(_logger, "Stopping, waiting for " + _outstandingRequests + " request(s) to drain.");
-                var drained = _shutdownSignal.WaitOne(Listener.Options.ShutdownTimeout);
-                if (drained)
-                {
-                    LogHelper.LogInfo(_logger, "All requests drained successfully.");
-                }
-                else
+
+                var waitForStop = new TaskCompletionSource<object>();
+                cancellationToken.Register(() =>
                 {
                     LogHelper.LogInfo(_logger, "Timed out, terminating " + _outstandingRequests + " request(s).");
-                }
+                    waitForStop.TrySetResult(0);
+                });
+
+                return Task.WhenAny(_shutdownSignal.Task, waitForStop.Task);
             }
-            // All requests are finished
+
+            return Task.CompletedTask;
+        }
+
+        public void Dispose()
+        {
+            _stopping = true;
             Listener.Dispose();
         }
 
diff --git a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/MessagePumpTests.cs b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/MessagePumpTests.cs
index 48913a746f..2bcd69e8c9 100644
--- a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/MessagePumpTests.cs
+++ b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/MessagePumpTests.cs
@@ -2,6 +2,7 @@
 // Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
 
 using System.Linq;
+using System.Threading;
 using Microsoft.AspNetCore.Hosting.Server.Features;
 using Microsoft.AspNetCore.Testing.xunit;
 using Microsoft.Extensions.Logging;
@@ -25,7 +26,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 serverAddressesFeature.PreferHostingUrls = true;
                 server.Listener.Options.UrlPrefixes.Add(serverAddress);
 
-                server.Start(new DummyApplication());
+                server.StartAsync(new DummyApplication(), CancellationToken.None).Wait();
 
                 Assert.Equal(overrideAddress, serverAddressesFeature.Addresses.Single());
             }
@@ -46,7 +47,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 serverAddressesFeature.Addresses.Add(overrideAddress);
                 server.Listener.Options.UrlPrefixes.Add(serverAddress);
 
-                server.Start(new DummyApplication());
+                server.StartAsync(new DummyApplication(), CancellationToken.None).Wait();
 
                 Assert.Equal(serverAddress, serverAddressesFeature.Addresses.Single());
             }
@@ -63,7 +64,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 serverAddressesFeature.PreferHostingUrls = true;
                 server.Listener.Options.UrlPrefixes.Add(serverAddress);
 
-                server.Start(new DummyApplication());
+                server.StartAsync(new DummyApplication(), CancellationToken.None).Wait();
 
                 Assert.Equal(serverAddress, serverAddressesFeature.Addresses.Single());
             }
@@ -84,7 +85,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 serverAddressesFeature.Addresses.Add(serverAddress);
                 server.Listener.Options.UrlPrefixes.Add(overrideAddress);
 
-                server.Start(new DummyApplication());
+                server.StartAsync(new DummyApplication(), CancellationToken.None).Wait();
 
                 Assert.Equal(overrideAddress, serverAddressesFeature.Addresses.Single());
             }
@@ -100,7 +101,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 var serverAddressesFeature = server.Features.Get<IServerAddressesFeature>();
                 serverAddressesFeature.Addresses.Add(serverAddress);
 
-                server.Start(new DummyApplication());
+                server.StartAsync(new DummyApplication(), CancellationToken.None).Wait();
             }
         }
 
@@ -109,7 +110,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
         {
             using (var server = new MessagePump(Options.Create(new HttpSysOptions()), new LoggerFactory()))
             {
-                server.Start(new DummyApplication());
+                server.StartAsync(new DummyApplication(), CancellationToken.None).Wait();
 
                 Assert.Equal(Constants.DefaultServerAddress, server.Features.Get<IServerAddressesFeature>().Addresses.Single());
             }
diff --git a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/RequestTests.cs b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/RequestTests.cs
index 1e79dff31b..91e4459b78 100644
--- a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/RequestTests.cs
+++ b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/RequestTests.cs
@@ -7,6 +7,7 @@ using System.Net;
 using System.Net.Http;
 using System.Net.Sockets;
 using System.Text;
+using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.AspNetCore.Hosting.Server;
 using Microsoft.AspNetCore.Http;
@@ -312,7 +313,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 server.Listener.Options.UrlPrefixes.Add(UrlPrefix.Create(rootUri.Scheme, rootUri.Host, rootUri.Port, path));
             }
 
-            server.Start(new DummyApplication(app));
+            server.StartAsync(new DummyApplication(app), CancellationToken.None).Wait();
             return server;
         }
 
diff --git a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/ServerTests.cs b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/ServerTests.cs
index 10a356b487..029c259b61 100644
--- a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/ServerTests.cs
+++ b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/ServerTests.cs
@@ -73,7 +73,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             Task<string> responseTask;
             ManualResetEvent received = new ManualResetEvent(false);
             string address;
-            using (Utilities.CreateHttpServer(out address, httpContext =>
+            using (var server = Utilities.CreateHttpServer(out address, httpContext =>
                 {
                     received.Set();
                     httpContext.Response.ContentLength = 11;
@@ -82,11 +82,34 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             {
                 responseTask = SendRequestAsync(address);
                 Assert.True(received.WaitOne(10000));
+                await server.StopAsync(new CancellationTokenSource(TimeSpan.FromSeconds(5)).Token);
             }
             string response = await responseTask;
             Assert.Equal("Hello World", response);
         }
 
+        [ConditionalFact]
+        public async Task Server_DisposeWithoutStopDuringRequest_Aborts()
+        {
+            Task<string> responseTask;
+            var received = new ManualResetEvent(false);
+            var stopped = new ManualResetEvent(false);
+            string address;
+            using (var server = Utilities.CreateHttpServer(out address, httpContext =>
+            {
+                received.Set();
+                Assert.True(stopped.WaitOne(TimeSpan.FromSeconds(10)));
+                httpContext.Response.ContentLength = 11;
+                return httpContext.Response.WriteAsync("Hello World");
+            }))
+            {
+                responseTask = SendRequestAsync(address);
+                Assert.True(received.WaitOne(TimeSpan.FromSeconds(10)));
+            }
+            stopped.Set();
+            await Assert.ThrowsAsync<HttpRequestException>(async () => await responseTask);
+        }
+
         [ConditionalFact]
         public async Task Server_ShutdownDuringLongRunningRequest_TimesOut()
         {
@@ -95,7 +118,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             bool? shutdown = null;
             var waitForShutdown = new ManualResetEvent(false);
             string address;
-            using (Utilities.CreateHttpServer(out address, httpContext =>
+            using (var server = Utilities.CreateHttpServer(out address, httpContext =>
             {
                 received.Set();
                 shutdown = waitForShutdown.WaitOne(TimeSpan.FromSeconds(15));
@@ -105,8 +128,9 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             {
                 responseTask = SendRequestAsync(address);
                 Assert.True(received.WaitOne(TimeSpan.FromSeconds(10)));
+                Assert.False(shutdown.HasValue);
+                await server.StopAsync(new CancellationTokenSource(TimeSpan.FromSeconds(5)).Token);
             }
-            Assert.False(shutdown.HasValue);
             waitForShutdown.Set();
             await Assert.ThrowsAsync<HttpRequestException>(async () => await responseTask);
         }
@@ -271,7 +295,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
 
             using (server)
             {
-                server.Start(new DummyApplication());
+                await server.StartAsync(new DummyApplication(), CancellationToken.None);
                 string response = await SendRequestAsync(address);
                 Assert.Equal(string.Empty, response);
             }
diff --git a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/Utilities.cs b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/Utilities.cs
index 3682e1de5e..5744e35d04 100644
--- a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/Utilities.cs
+++ b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/Utilities.cs
@@ -2,6 +2,7 @@
 // Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
 
 using System;
+using System.Threading;
 using Microsoft.AspNetCore.Hosting.Server;
 using Microsoft.AspNetCore.Hosting.Server.Features;
 using Microsoft.AspNetCore.Http;
@@ -55,7 +56,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                     server.Listener.Options.Authentication.AllowAnonymous = allowAnonymous;
                     try
                     {
-                        server.Start(new DummyApplication(app));
+                        server.StartAsync(new DummyApplication(app), CancellationToken.None).Wait();
                         return server;
                     }
                     catch (HttpSysException)
@@ -76,7 +77,7 @@ namespace Microsoft.AspNetCore.Server.HttpSys
         {
             var server = new MessagePump(Options.Create(new HttpSysOptions()), new LoggerFactory());
             server.Features.Get<IServerAddressesFeature>().Addresses.Add(UrlPrefix.Create(scheme, host, port, path).ToString());
-            server.Start(new DummyApplication(app));
+            server.StartAsync(new DummyApplication(app), CancellationToken.None).Wait();
             return server;
         }
     }