diff --git a/eng/packaging.targets b/eng/packaging.targets
index f5a82c3d36e93e..b1d859952ccf5a 100644
--- a/eng/packaging.targets
+++ b/eng/packaging.targets
@@ -19,9 +19,8 @@
                                        '$(IsRIDSpecificProject)' == 'true') and
                                        '$(PreReleaseVersionLabel)' != 'servicing' and
                                        '$(GitHubRepositoryName)' != 'runtimelab'">true</GeneratePackageOnBuild>
-    <GeneratePackageOnBuild Condition="'$(GeneratePackageOnBuild)' != 'true'">false</GeneratePackageOnBuild>
     <!-- When in source-build we need to generate all packages when building for all configurations even in servicing. -->
-    <GeneratePackageOnBuild Condition="!$(GeneratePackageOnBuild) and
+    <GeneratePackageOnBuild Condition="'$(GeneratePackageOnBuild)' != 'true' and
                                        '$(BuildAllConfigurations)' == 'true' and
                                        '$(DotNetBuildFromSource)' == 'true'">true</GeneratePackageOnBuild>
     <!-- Search for the documentation file in the intellisense package and otherwise pick up the generated one. -->
diff --git a/src/libraries/Microsoft.Internal.Runtime.AspNetCore.Transport/src/Microsoft.Internal.Runtime.AspNetCore.Transport.proj b/src/libraries/Microsoft.Internal.Runtime.AspNetCore.Transport/src/Microsoft.Internal.Runtime.AspNetCore.Transport.proj
index cd8628c81afd08..9f63a459918dbf 100644
--- a/src/libraries/Microsoft.Internal.Runtime.AspNetCore.Transport/src/Microsoft.Internal.Runtime.AspNetCore.Transport.proj
+++ b/src/libraries/Microsoft.Internal.Runtime.AspNetCore.Transport/src/Microsoft.Internal.Runtime.AspNetCore.Transport.proj
@@ -13,6 +13,12 @@
     <NoWarn>$(NoWarn);NU5131</NoWarn>
   </PropertyGroup>
 
+  <!-- Always generate this package during servicing to flow the dependency to AspNetCore. -->
+  <PropertyGroup Condition="'$(PreReleaseVersionLabel)' == 'servicing'">
+    <GeneratePackageOnBuild>true</GeneratePackageOnBuild>
+    <ServicingVersion>$(PatchVersion)</ServicingVersion>
+  </PropertyGroup>
+
   <ItemGroup>
     <!-- Requires Private=true to calculate ReferenceCopyLocalPaths items. -->
     <ProjectReference Include="@(AspNetCoreAppLibrary->'$(LibrariesProjectRoot)%(Identity)\src\%(Identity).csproj')"
diff --git a/src/libraries/Microsoft.Internal.Runtime.WindowsDesktop.Transport/src/Microsoft.Internal.Runtime.WindowsDesktop.Transport.proj b/src/libraries/Microsoft.Internal.Runtime.WindowsDesktop.Transport/src/Microsoft.Internal.Runtime.WindowsDesktop.Transport.proj
index 4fd7866e89e358..6d7a255a94c9de 100644
--- a/src/libraries/Microsoft.Internal.Runtime.WindowsDesktop.Transport/src/Microsoft.Internal.Runtime.WindowsDesktop.Transport.proj
+++ b/src/libraries/Microsoft.Internal.Runtime.WindowsDesktop.Transport/src/Microsoft.Internal.Runtime.WindowsDesktop.Transport.proj
@@ -13,6 +13,12 @@
     <NoWarn>$(NoWarn);NU5131</NoWarn>
   </PropertyGroup>
 
+  <!-- Always generate this package during servicing to flow the dependency to WindowsDesktop. -->
+  <PropertyGroup Condition="'$(PreReleaseVersionLabel)' == 'servicing'">
+    <GeneratePackageOnBuild>true</GeneratePackageOnBuild>
+    <ServicingVersion>$(PatchVersion)</ServicingVersion>
+  </PropertyGroup>
+
   <ItemGroup>
     <!-- Requires Private=true to calculate ReferenceCopyLocalPaths items.
          ReferringTargetFramework is set to $(NetCoreAppCurrent)-windows so that we pack the Windows specific implementation assemblies -->