diff --git a/src/Servers/HttpSys/samples/SelfHostServer/SelfHostServer.csproj b/src/Servers/HttpSys/samples/SelfHostServer/SelfHostServer.csproj
index cf4b7f8a960e..35450964c9ef 100644
--- a/src/Servers/HttpSys/samples/SelfHostServer/SelfHostServer.csproj
+++ b/src/Servers/HttpSys/samples/SelfHostServer/SelfHostServer.csproj
@@ -1,10 +1,15 @@
-<Project Sdk="Microsoft.NET.Sdk">
+<Project Sdk="Microsoft.NET.Sdk">
 
   <PropertyGroup>
     <TargetFramework>$(DefaultNetCoreTargetFramework)</TargetFramework>
     <OutputType>Exe</OutputType>
     <ServerGarbageCollection>true</ServerGarbageCollection>
   </PropertyGroup>
+  
+  <PropertyGroup>
+    <!--Imitate IIS Express so we can use it's cert bindings-->
+    <PackageTags>214124cd-d05b-4309-9af9-9caa44b2b74a</PackageTags>
+  </PropertyGroup>
 
   <ItemGroup>
     <Reference Include="Microsoft.AspNetCore.Server.HttpSys" />
diff --git a/src/Servers/HttpSys/samples/SelfHostServer/Startup.cs b/src/Servers/HttpSys/samples/SelfHostServer/Startup.cs
index 52b65bd248c0..42f6d11f81e5 100644
--- a/src/Servers/HttpSys/samples/SelfHostServer/Startup.cs
+++ b/src/Servers/HttpSys/samples/SelfHostServer/Startup.cs
@@ -37,6 +37,8 @@ public static void Main(string[] args)
                 .UseHttpSys(options =>
                 {
                     options.UrlPrefixes.Add("http://localhost:5000");
+                    // This is a pre-configured IIS express port. See the PackageTags in the csproj.
+                    options.UrlPrefixes.Add("https://localhost:44319");
                     options.Authentication.Schemes = AuthenticationSchemes.None;
                     options.Authentication.AllowAnonymous = true;
                 })
diff --git a/src/Servers/HttpSys/src/NativeInterop/ComNetOS.cs b/src/Servers/HttpSys/src/NativeInterop/ComNetOS.cs
index 12d1381baeb7..f2b693c1d150 100644
--- a/src/Servers/HttpSys/src/NativeInterop/ComNetOS.cs
+++ b/src/Servers/HttpSys/src/NativeInterop/ComNetOS.cs
@@ -2,7 +2,6 @@
 // Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
 
 using System;
-using Microsoft.Extensions.Internal;
 
 namespace Microsoft.AspNetCore.Server.HttpSys
 {
diff --git a/src/Servers/HttpSys/src/RequestProcessing/Response.cs b/src/Servers/HttpSys/src/RequestProcessing/Response.cs
index b31dc4809ef5..5f29763d2ff5 100644
--- a/src/Servers/HttpSys/src/RequestProcessing/Response.cs
+++ b/src/Servers/HttpSys/src/RequestProcessing/Response.cs
@@ -4,7 +4,6 @@
 using System;
 using System.Collections.Generic;
 using System.Diagnostics;
-using System.Globalization;
 using System.IO;
 using System.Runtime.InteropServices;
 using System.Threading;
@@ -18,6 +17,9 @@ namespace Microsoft.AspNetCore.Server.HttpSys
 {
     internal sealed class Response
     {
+        // Support is assumed until we get an error and turn it off.
+        private static bool SupportsGoAway = true;
+
         private ResponseState _responseState;
         private string _reasonPhrase;
         private ResponseBody _nativeStream;
@@ -314,6 +316,31 @@ internal unsafe uint SendHeaders(HttpApiTypes.HTTP_DATA_CHUNK[] dataChunks,
                                 asyncResult == null ? SafeNativeOverlapped.Zero : asyncResult.NativeOverlapped,
                                 IntPtr.Zero);
 
+                        // GoAway is only supported on later versions. Retry.
+                        if (statusCode == ErrorCodes.ERROR_INVALID_PARAMETER
+                            && (flags & HttpApiTypes.HTTP_FLAGS.HTTP_SEND_RESPONSE_FLAG_GOAWAY) != 0)
+                        {
+                            flags &= ~HttpApiTypes.HTTP_FLAGS.HTTP_SEND_RESPONSE_FLAG_GOAWAY;
+                            statusCode =
+                                HttpApi.HttpSendHttpResponse(
+                                    RequestContext.Server.RequestQueue.Handle,
+                                    Request.RequestId,
+                                    (uint)flags,
+                                    pResponse,
+                                    &cachePolicy,
+                                    &bytesSent,
+                                    IntPtr.Zero,
+                                    0,
+                                    asyncResult == null ? SafeNativeOverlapped.Zero : asyncResult.NativeOverlapped,
+                                    IntPtr.Zero);
+
+                            // Succeeded without GoAway, disable them.
+                            if (statusCode != ErrorCodes.ERROR_INVALID_PARAMETER)
+                            {
+                                SupportsGoAway = false;
+                            }
+                        }
+
                         if (asyncResult != null &&
                             statusCode == ErrorCodes.ERROR_SUCCESS &&
                             HttpSysListener.SkipIOCPCallbackOnSuccess)
@@ -417,6 +444,10 @@ internal HttpApiTypes.HTTP_FLAGS ComputeHeaders(long writeCount, bool endOfReque
                     Headers.Append(HttpKnownHeaderNames.Connection, Constants.Close);
                 }
                 flags = HttpApiTypes.HTTP_FLAGS.HTTP_SEND_RESPONSE_FLAG_DISCONNECT;
+                if (responseCloseSet && requestVersion >= Constants.V2 && SupportsGoAway)
+                {
+                    flags |= HttpApiTypes.HTTP_FLAGS.HTTP_SEND_RESPONSE_FLAG_GOAWAY;
+                }
             }
 
             Headers.IsReadOnly = true;
diff --git a/src/Shared/HttpSys/NativeInterop/HttpApiTypes.cs b/src/Shared/HttpSys/NativeInterop/HttpApiTypes.cs
index 324426c60dbc..80a06607cbad 100644
--- a/src/Shared/HttpSys/NativeInterop/HttpApiTypes.cs
+++ b/src/Shared/HttpSys/NativeInterop/HttpApiTypes.cs
@@ -602,6 +602,7 @@ internal enum HTTP_FLAGS : uint
             HTTP_INITIALIZE_SERVER = 0x00000001,
             HTTP_INITIALIZE_CBT = 0x00000004,
             HTTP_SEND_RESPONSE_FLAG_OPAQUE = 0x00000040,
+            HTTP_SEND_RESPONSE_FLAG_GOAWAY = 0x00000100,
         }
 
         [Flags]