diff --git a/src/libraries/sendtohelixhelp.proj b/src/libraries/sendtohelixhelp.proj
index 14ab6568ae292b..b71e0872b4eb3a 100644
--- a/src/libraries/sendtohelixhelp.proj
+++ b/src/libraries/sendtohelixhelp.proj
@@ -268,11 +268,11 @@
     <Message Importance="High" Text="Using Timeout: $(_workItemTimeout)" />
 
     <PropertyGroup Condition="'$(RuntimeFlavor)' == 'CoreCLR' and '$(BUILD_BUILDID)' != ''">
-      <HelixPostCommands Condition="'$(TargetOS)' == 'windows'">
+      <HelixPostCommands Condition="'$(WindowsShell)' == 'true'">
         $(HelixPostCommands);
         %HELIX_PYTHONPATH% %HELIX_CORRELATION_PAYLOAD%\gen-debug-dump-docs.py -buildid $(BUILD_BUILDID) -workitem %HELIX_WORKITEM_FRIENDLYNAME% -jobid %HELIX_CORRELATION_ID% -outdir %HELIX_WORKITEM_UPLOAD_ROOT% -templatedir %HELIX_CORRELATION_PAYLOAD% -dumpdir %HELIX_DUMP_FOLDER% -productver $(ProductVersion)
       </HelixPostCommands>
-      <HelixPostCommands Condition="'$(TargetOS)' != 'windows' and '$(TargetOS)' != 'browser' and '$(TargetOS)' != 'wasi'">
+      <HelixPostCommands Condition="'$(WindowsShell)' != 'true' and '$(TargetOS)' != 'browser' and '$(TargetOS)' != 'wasi'">
         $(HelixPostCommands);
         $HELIX_PYTHONPATH $HELIX_CORRELATION_PAYLOAD/gen-debug-dump-docs.py -buildid $(BUILD_BUILDID) -workitem $HELIX_WORKITEM_FRIENDLYNAME -jobid $HELIX_CORRELATION_ID -outdir $HELIX_WORKITEM_UPLOAD_ROOT -templatedir $HELIX_CORRELATION_PAYLOAD -dumpdir $HELIX_DUMP_FOLDER -productver $(ProductVersion)
       </HelixPostCommands>