diff --git a/eng/pipelines/runtime-linker-tests.yml b/eng/pipelines/runtime-linker-tests.yml
index a14af99374f919..ceffb1e237e76c 100644
--- a/eng/pipelines/runtime-linker-tests.yml
+++ b/eng/pipelines/runtime-linker-tests.yml
@@ -59,7 +59,7 @@ jobs:
     jobTemplate: /eng/pipelines/common/global-build-job.yml
     buildConfig: release
     platforms:
-#    - Windows_NT_x64
+    - Windows_NT_x64
     - OSX_x64
     - Linux_x64
     jobParameters:
diff --git a/src/libraries/pretest.proj b/src/libraries/pretest.proj
index 1ba9c731246433..23a4041ff30a66 100644
--- a/src/libraries/pretest.proj
+++ b/src/libraries/pretest.proj
@@ -87,11 +87,9 @@
     <ItemGroup>
       <_refPackLibFile Include="$(MicrosoftNetCoreAppRefPackRefDir)*.*">
         <TargetPath>ref/$(NetCoreAppCurrent)</TargetPath>
-        <IsSymbolFile Condition="$([System.String]::Copy('%(Identity)').EndsWith('pdb'))">true</IsSymbolFile>
       </_refPackLibFile>
       <_runtimePackLibFiles Include="$(MicrosoftNetCoreAppRuntimePackRidLibTfmDir)*.*">
         <TargetPath>runtimes/$(PackageRID)/lib/$(NetCoreAppCurrent)</TargetPath>
-        <IsSymbolFile Condition="$([System.String]::Copy('%(Identity)').EndsWith('pdb'))">true</IsSymbolFile>
       </_runtimePackLibFiles>
       <_runtimePackNativeFiles Include="$(MicrosoftNetCoreAppRuntimePackNativeDir)*.*">
         <TargetPath>runtimes/$(PackageRID)/native</TargetPath>
@@ -106,6 +104,20 @@
       <FrameworkListRootAttributes Include="FrameworkName" Value="$(SharedFrameworkName)" />
     </ItemGroup>
 
+    <!-- We need to set this metadata in a separate ItemGroup than when the Items are initially populated in order to
+    have access to the Extension metadata. -->
+    <ItemGroup>
+      <_refPackLibFile>
+        <IsSymbolFile Condition="'%(Extension)' == '.pdb'">true</IsSymbolFile>
+      </_refPackLibFile>
+      <_runtimePackLibFiles>
+        <IsSymbolFile Condition="'%(Extension)' == '.pdb'">true</IsSymbolFile>
+      </_runtimePackLibFiles>
+      <_runtimePackNativeFiles>
+        <IsSymbolFile Condition="'%(Extension)' == '.pdb'">true</IsSymbolFile>
+      </_runtimePackNativeFiles>
+    </ItemGroup>
+
     <CreateFrameworkListFile Files="@(_refPackLibFile)"
                              TargetFile="$(MicrosoftNetCoreAppRefPackDataDir)FrameworkList.xml"
                              TargetFilePrefixes="ref/;runtimes/"