diff --git a/src/coreclr/nativeaot/BuildIntegration/Microsoft.NETCore.Native.Publish.targets b/src/coreclr/nativeaot/BuildIntegration/Microsoft.NETCore.Native.Publish.targets
index 610ae55338e49d..f44198d00af9a6 100644
--- a/src/coreclr/nativeaot/BuildIntegration/Microsoft.NETCore.Native.Publish.targets
+++ b/src/coreclr/nativeaot/BuildIntegration/Microsoft.NETCore.Native.Publish.targets
@@ -52,7 +52,10 @@
       </ResolvedFileToPublish>
       <_AggregateExecutableShimSymbolRecursivePath Include="%(_AggregateExecutableReferencePath.ShimSymbol)/**/*"
                                              Condition="'$(_AggregateExecutable)' == 'true' and '$(CopyOutputSymbolsToPublishDirectory)' == 'true' and '$(NativeSymbolExt)' == '.dSYM' and Exists('%(_AggregateExecutableReferencePath.ShimSymbol)')">
-        <RelativePath>%(_AggregateExecutableReferencePath.AssemblyName)$(NativeSymbolExt)/%(RecursiveDir)%(Filename)%(Extension)</RelativePath>
+        <SymbolBundleName>%(_AggregateExecutableReferencePath.AssemblyName)$(NativeSymbolExt)</SymbolBundleName>
+      </_AggregateExecutableShimSymbolRecursivePath>
+      <_AggregateExecutableShimSymbolRecursivePath Update="@(_AggregateExecutableShimSymbolRecursivePath)">
+        <RelativePath>%(_AggregateExecutableShimSymbolRecursivePath.SymbolBundleName)/%(_AggregateExecutableShimSymbolRecursivePath.RecursiveDir)%(_AggregateExecutableShimSymbolRecursivePath.Filename)%(_AggregateExecutableShimSymbolRecursivePath.Extension)</RelativePath>
       </_AggregateExecutableShimSymbolRecursivePath>
       <ResolvedFileToPublish Include="@(_AggregateExecutableShimSymbolRecursivePath)"
                              Condition="'$(_AggregateExecutable)' == 'true' and '$(CopyOutputSymbolsToPublishDirectory)' == 'true'">
diff --git a/src/tests/nativeaot/AggregateExecutableLibrary/AggregateLibrary.csproj b/src/tests/nativeaot/AggregateExecutableLibrary/AggregateLibrary.csproj
index 730c7c1181824d..6252c8284f7ee3 100644
--- a/src/tests/nativeaot/AggregateExecutableLibrary/AggregateLibrary.csproj
+++ b/src/tests/nativeaot/AggregateExecutableLibrary/AggregateLibrary.csproj
@@ -16,6 +16,8 @@
     <CLRTestRunFile Condition="'$(TargetsWindows)' != 'true'">./native/ValidatorExe</CLRTestRunFile>
     <SkipInferOutputType>true</SkipInferOutputType>
     <EnablePreviewFeatures>true</EnablePreviewFeatures>
+    <NativeDebugSymbols Condition="'$(TargetsOSX)' == 'true'">true</NativeDebugSymbols>
+    <CopyOutputSymbolsToPublishDirectory Condition="'$(TargetsOSX)' == 'true'">true</CopyOutputSymbolsToPublishDirectory>
     <!-- warning CS2008: No source files specified -->
     <NoWarn>$(NoWarn);CS2008</NoWarn>
   </PropertyGroup>
@@ -31,6 +33,12 @@
     </PropertyGroup>
   </Target>
 
+  <Target Name="UseDsymAggregateExecutableShimSymbols" BeforeTargets="ComputeAggregateExecutableInputs" Condition="'$(TargetsOSX)' == 'true'">
+    <PropertyGroup>
+      <NativeSymbolExt>.dSYM</NativeSymbolExt>
+    </PropertyGroup>
+  </Target>
+
   <Target Name="WriteHelixExtraExecutablesList" AfterTargets="NativeCompile" Condition="'$(TargetsWindows)' != 'true'">
     <PropertyGroup>
       <_HelloExeRelative>$(BuildProjectRelativeDir)native/HelloExe</_HelloExeRelative>
@@ -39,4 +47,16 @@
 
     <WriteLinesToFile File="$(TargetDir)helix-extra-executables.list" Lines="$(_HelloExeRelative)" Overwrite="true" WriteOnlyWhenDifferent="true" />
   </Target>
+
+  <Target Name="ValidateAggregateExecutableShimSymbols" AfterTargets="NativeCompile" Condition="'$(TargetsOSX)' == 'true'">
+    <ItemGroup>
+      <_ExpectedAggregateExecutableShimSymbol Include="HelloExe.dSYM/Contents/Info.plist" />
+      <_ExpectedAggregateExecutableShimSymbol Include="HelloExe.dSYM/Contents/Resources/DWARF/HelloExe" />
+      <_PublishedFileRelativePath Include="@(ResolvedFileToPublish->'%(RelativePath)')" />
+      <_MissingAggregateExecutableShimSymbol Include="@(_ExpectedAggregateExecutableShimSymbol)" Exclude="@(_PublishedFileRelativePath)" />
+    </ItemGroup>
+
+    <Error Condition="'@(_MissingAggregateExecutableShimSymbol)' != ''"
+           Text="Aggregate executable shim symbol files have incorrect publish paths: @(_MissingAggregateExecutableShimSymbol, ', ')" />
+  </Target>
 </Project>