diff --git a/src/Microsoft.AspNetCore.Server.HttpSys/HttpSysOptions.cs b/src/Microsoft.AspNetCore.Server.HttpSys/HttpSysOptions.cs
index 2c97b4e..fe0c6d1 100644
--- a/src/Microsoft.AspNetCore.Server.HttpSys/HttpSysOptions.cs
+++ b/src/Microsoft.AspNetCore.Server.HttpSys/HttpSysOptions.cs
@@ -81,6 +81,12 @@ public long RequestQueueLimit
             }
         }
 
+        /// <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 bd6dbec..2392156 100644
--- a/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs
+++ b/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs
@@ -221,7 +221,15 @@ public void Dispose()
             if (_outstandingRequests > 0)
             {
                 LogHelper.LogInfo(_logger, "Stopping, waiting for " + _outstandingRequests + " request(s) to drain.");
-                _shutdownSignal.WaitOne();
+                var drained = _shutdownSignal.WaitOne(Listener.Options.ShutdownTimeout);
+                if (drained)
+                {
+                    LogHelper.LogInfo(_logger, "All requests drained successfully.");
+                }
+                else
+                {
+                    LogHelper.LogInfo(_logger, "Timed out, terminating " + _outstandingRequests + " request(s).");
+                }
             }
             // All requests are finished
             _listener.Dispose();
diff --git a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/ServerTests.cs b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/ServerTests.cs
index 2794e46..2ae9440 100644
--- a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/ServerTests.cs
+++ b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/ServerTests.cs
@@ -68,7 +68,7 @@ public async Task Server_EchoHelloWorld_Success()
         }
 
         [ConditionalFact]
-        public async Task Server_ShutdownDurringRequest_Success()
+        public async Task Server_ShutdownDuringRequest_Success()
         {
             Task<string> responseTask;
             ManualResetEvent received = new ManualResetEvent(false);
@@ -87,6 +87,30 @@ public async Task Server_ShutdownDurringRequest_Success()
             Assert.Equal("Hello World", response);
         }
 
+        [ConditionalFact]
+        public async Task Server_ShutdownDuringLongRunningRequest_TimesOut()
+        {
+            Task<string> responseTask;
+            var received = new ManualResetEvent(false);
+            bool? shutdown = null;
+            var waitForShutdown = new ManualResetEvent(false);
+            string address;
+            using (Utilities.CreateHttpServer(out address, httpContext =>
+            {
+                received.Set();
+                shutdown = waitForShutdown.WaitOne(TimeSpan.FromSeconds(15));
+                httpContext.Response.ContentLength = 11;
+                return httpContext.Response.WriteAsync("Hello World");
+            }))
+            {
+                responseTask = SendRequestAsync(address);
+                Assert.True(received.WaitOne(TimeSpan.FromSeconds(10)));
+            }
+            Assert.False(shutdown.HasValue);
+            waitForShutdown.Set();
+            await Assert.ThrowsAsync<HttpRequestException>(async () => await responseTask);
+        }
+
         [ConditionalFact]
         public void Server_AppException_ClientReset()
         {