diff --git a/src/Servers/HttpSys/src/StandardFeatureCollection.cs b/src/Servers/HttpSys/src/StandardFeatureCollection.cs
index 69158b62d1..88c1f7bff9 100644
--- a/src/Servers/HttpSys/src/StandardFeatureCollection.cs
+++ b/src/Servers/HttpSys/src/StandardFeatureCollection.cs
@@ -20,8 +20,6 @@ namespace Microsoft.AspNetCore.Server.HttpSys
             { typeof(IHttpResponseFeature), _identityFunc },
             { typeof(IHttpSendFileFeature), _identityFunc },
             { typeof(ITlsConnectionFeature), ctx => ctx.GetTlsConnectionFeature() },
-            { typeof(ITlsHandshakeFeature), ctx => ctx.GetTlsHandshakeFeature() },
-            // { typeof(ITlsTokenBindingFeature), ctx => ctx.GetTlsTokenBindingFeature() }, TODO: https://github.com/aspnet/HttpSysServer/issues/231
             { typeof(IHttpBufferingFeature), _identityFunc },
             { typeof(IHttpRequestLifetimeFeature), _identityFunc },
             { typeof(IHttpAuthenticationFeature), _identityFunc },
@@ -41,6 +39,8 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 // SignalR uses the presence of the feature to detect feature support.
                 // https://github.com/aspnet/HttpSysServer/issues/427
                 _featureFuncLookup[typeof(IHttpUpgradeFeature)] = _identityFunc;
+                // Win8+
+                _featureFuncLookup[typeof(ITlsHandshakeFeature)] = ctx => ctx.GetTlsHandshakeFeature();
             }
         }
 
diff --git a/src/Servers/HttpSys/test/FunctionalTests/HttpsTests.cs b/src/Servers/HttpSys/test/FunctionalTests/HttpsTests.cs
index d3e4fa54ce..7b99af24a4 100644
--- a/src/Servers/HttpSys/test/FunctionalTests/HttpsTests.cs
+++ b/src/Servers/HttpSys/test/FunctionalTests/HttpsTests.cs
@@ -102,9 +102,32 @@ namespace Microsoft.AspNetCore.Server.HttpSys
         }
 
         [ConditionalFact]
+        [OSDontSkipCondition(OperatingSystems.Windows, WindowsVersions.Win7, WindowsVersions.Win2008R2)]
+        public async Task Https_SkipsITlsHandshakeFeatureOnWin7()
+        {
+            using (Utilities.CreateDynamicHttpsServer(out var address, async httpContext =>
+            {
+                try
+                {
+                    var tlsFeature = httpContext.Features.Get<ITlsHandshakeFeature>();
+                    Assert.Null(tlsFeature);
+                }
+                catch (Exception ex)
+                {
+                    await httpContext.Response.WriteAsync(ex.ToString());
+                }
+            }))
+            {
+                string response = await SendRequestAsync(address);
+                Assert.Equal(string.Empty, response);
+            }
+        }
+
+        [ConditionalFact]
+        [OSSkipCondition(OperatingSystems.Windows, WindowsVersions.Win7, WindowsVersions.Win2008R2)]
         public async Task Https_SetsITlsHandshakeFeature()
         {
-            using (Utilities.CreateDynamicHttpsServer(out var address, httpContext =>
+            using (Utilities.CreateDynamicHttpsServer(out var address, async httpContext =>
             {
                 try
                 {
@@ -121,9 +144,8 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 }
                 catch (Exception ex)
                 {
-                    return httpContext.Response.WriteAsync(ex.ToString());
+                    await httpContext.Response.WriteAsync(ex.ToString());
                 }
-                return Task.FromResult(0);
             }))
             {
                 string response = await SendRequestAsync(address);