diff --git a/eng/packaging.targets b/eng/packaging.targets
index 3c14f61ae32b6..72401ef6da063 100644
--- a/eng/packaging.targets
+++ b/eng/packaging.targets
@@ -44,9 +44,9 @@
     <VersionPrefix>$(MajorVersion).$(MinorVersion).$(ServicingVersion)</VersionPrefix>
     <_IsWindowsDesktopApp Condition="$(WindowsDesktopCoreAppLibrary.Contains('$(AssemblyName);'))">true</_IsWindowsDesktopApp>
     <_IsAspNetCoreApp Condition="$(AspNetCoreAppLibrary.Contains('$(AssemblyName);'))">true</_IsAspNetCoreApp>
-    <_AssemblyInTargetingPack Condition="'$(IsNETCoreAppSrc)' == 'true' or '$(_IsAspNetCoreApp)' == 'true' or '$(_IsWindowsDesktopApp)' == 'true'">true</_AssemblyInTargetingPack>
+    <_AssemblyInTargetingPack Condition="('$(IsNETCoreAppSrc)' == 'true' or '$(_IsAspNetCoreApp)' == 'true' or '$(_IsWindowsDesktopApp)' == 'true') and '$(TargetFrameworkIdentifier)' != '.NETFramework'">true</_AssemblyInTargetingPack>
     <!-- Assembly version do not get updated in non-netfx ref pack assemblies. -->
-    <AssemblyVersion Condition="'$(_AssemblyInTargetingPack)' != 'true' or '$(TargetFrameworkIdentifier)' == '.NETFramework'">$(MajorVersion).$(MinorVersion).0.$(ServicingVersion)</AssemblyVersion>
+    <AssemblyVersion Condition="'$(_AssemblyInTargetingPack)' != 'true'">$(MajorVersion).$(MinorVersion).0.$(ServicingVersion)</AssemblyVersion>
   </PropertyGroup>
 
   <ItemGroup Condition="'$(EnablePackageValidation)' == 'true'">
diff --git a/src/libraries/System.IO.Pipelines/src/System.IO.Pipelines.csproj b/src/libraries/System.IO.Pipelines/src/System.IO.Pipelines.csproj
index 34f79827374ac..a58b8c1af08d0 100644
--- a/src/libraries/System.IO.Pipelines/src/System.IO.Pipelines.csproj
+++ b/src/libraries/System.IO.Pipelines/src/System.IO.Pipelines.csproj
@@ -9,6 +9,8 @@ Commonly Used Types:
 System.IO.Pipelines.Pipe
 System.IO.Pipelines.PipeWriter
 System.IO.Pipelines.PipeReader</PackageDescription>
+    <GeneratePackageOnBuild>true</GeneratePackageOnBuild>
+    <ServicingVersion>1</ServicingVersion>
   </PropertyGroup>
   <ItemGroup>
     <Compile Include="$(CommonPath)System\Threading\Tasks\TaskToApm.cs"
diff --git a/src/libraries/System.IO.Pipelines/src/System/IO/Pipelines/PipeAwaitable.cs b/src/libraries/System.IO.Pipelines/src/System/IO/Pipelines/PipeAwaitable.cs
index fb25780a3fab4..aba52f13e9646 100644
--- a/src/libraries/System.IO.Pipelines/src/System/IO/Pipelines/PipeAwaitable.cs
+++ b/src/libraries/System.IO.Pipelines/src/System/IO/Pipelines/PipeAwaitable.cs
@@ -47,16 +47,33 @@ public void BeginOperation(CancellationToken cancellationToken, Action<object?>
         {
             cancellationToken.ThrowIfCancellationRequested();
 
-            _awaitableState |= AwaitableState.Running;
-
             // Don't register if already completed, we would immediately unregistered in ObserveCancellation
             if (cancellationToken.CanBeCanceled && !IsCompleted)
             {
+#if DEBUG
+                var previousAwaitableState = _awaitableState;
+#endif
+
+                _cancellationTokenRegistration = cancellationToken.UnsafeRegister(callback, state);
+
+                // If we get back the default CancellationTokenRegistration then it means the
+                // callback synchronously and we can throw inline. This is safe because we haven't changed
+                // the state of the awaitable as yet.
+                if (_cancellationTokenRegistration == default(CancellationTokenRegistration))
+                {
+#if DEBUG
+                    Debug.Assert(previousAwaitableState == _awaitableState, "The awaitable state changed!");
+#endif
+
+                    cancellationToken.ThrowIfCancellationRequested();
+                }
+
 #if (NETSTANDARD2_0 || NETFRAMEWORK)
                 _cancellationToken = cancellationToken;
 #endif
-                _cancellationTokenRegistration = cancellationToken.UnsafeRegister(callback, state);
             }
+
+            _awaitableState |= AwaitableState.Running;
         }
 
         [MethodImpl(MethodImplOptions.AggressiveInlining)]