diff --git a/src/libraries/System.Net.Http.WinHttpHandler/src/System.Net.Http.WinHttpHandler.csproj b/src/libraries/System.Net.Http.WinHttpHandler/src/System.Net.Http.WinHttpHandler.csproj
index 8959c43540ca16..65ec45bc444f7c 100644
--- a/src/libraries/System.Net.Http.WinHttpHandler/src/System.Net.Http.WinHttpHandler.csproj
+++ b/src/libraries/System.Net.Http.WinHttpHandler/src/System.Net.Http.WinHttpHandler.csproj
@@ -4,8 +4,8 @@
     <IncludeDllSafeSearchPathAttribute>true</IncludeDllSafeSearchPathAttribute>
     <AllowUnsafeBlocks>true</AllowUnsafeBlocks>
     <IsPackable>true</IsPackable>
-    <GeneratePackageOnBuild>false</GeneratePackageOnBuild>
-    <ServicingVersion>2</ServicingVersion>
+    <GeneratePackageOnBuild>true</GeneratePackageOnBuild>
+    <ServicingVersion>3</ServicingVersion>
     <PackageDescription>Provides a message handler for HttpClient based on the WinHTTP interface of Windows. While similar to HttpClientHandler, it provides developers more granular control over the application's HTTP communication than the HttpClientHandler.
 
 Commonly Used Types:
diff --git a/src/libraries/System.Net.Http.WinHttpHandler/src/System/Net/Http/WinHttpRequestCallback.cs b/src/libraries/System.Net.Http.WinHttpHandler/src/System/Net/Http/WinHttpRequestCallback.cs
index 13c154516ce82c..7542c42fab9b49 100644
--- a/src/libraries/System.Net.Http.WinHttpHandler/src/System/Net/Http/WinHttpRequestCallback.cs
+++ b/src/libraries/System.Net.Http.WinHttpHandler/src/System/Net/Http/WinHttpRequestCallback.cs
@@ -231,13 +231,12 @@ private static void OnRequestRedirect(WinHttpRequestState state, Uri redirectUri
         private static void OnRequestSendingRequest(WinHttpRequestState state)
         {
             Debug.Assert(state != null, "OnRequestSendingRequest: state is null");
-            Debug.Assert(state.RequestHandle != null, "OnRequestSendingRequest: state.RequestHandle is null");
             Debug.Assert(state.RequestMessage != null, "OnRequestSendingRequest: state.RequestMessage is null");
             Debug.Assert(state.RequestMessage.RequestUri != null, "OnRequestSendingRequest: state.RequestMessage.RequestUri is null");
 
-            if (state.RequestMessage.RequestUri.Scheme != UriScheme.Https)
+            if (state.RequestMessage.RequestUri.Scheme != UriScheme.Https || state.RequestHandle == null)
             {
-                // Not SSL/TLS.
+                // Not SSL/TLS or request already gone
                 return;
             }