diff --git a/eng/liveBuilds.targets b/eng/liveBuilds.targets
index 51f990bd229ea5..25415b2d7b091a 100644
--- a/eng/liveBuilds.targets
+++ b/eng/liveBuilds.targets
@@ -103,7 +103,9 @@
         Include="
           $(CoreCLRSharedFrameworkPdbDir)*.pdb;
           $(CoreCLRSharedFrameworkPdbDir)*.dbg;
-          $(CoreCLRSharedFrameworkPdbDir)*.dwarf" IsNative="true" />
+          $(CoreCLRSharedFrameworkPdbDir)*.dwarf;
+          $(CoreCLRSharedFrameworkPdbDir)*.dSYM"
+          IsNative="true" />
       <RuntimeFiles Condition="Exists('$(CoreCLRArtifactsPdbDir)System.Private.CoreLib.pdb')"
         Include="$(CoreCLRArtifactsPdbDir)System.Private.CoreLib.pdb" />
       <RuntimeFiles Condition="Exists('$(CoreCLRArtifactsPdbDir)System.Private.CoreLib.ni.pdb')"
@@ -113,7 +115,8 @@
         Include="
           $(CoreCLRSharedFrameworkPdbDir)*.pdb;
           $(CoreCLRSharedFrameworkPdbDir)*.dbg;
-          $(CoreCLRSharedFrameworkPdbDir)*.dwarf" />
+          $(CoreCLRSharedFrameworkPdbDir)*.dwarf;
+          $(CoreCLRSharedFrameworkPdbDir)*.dSYM" />
 
       <CoreCLRCrossTargetFiles>
         <TargetPath>runtime/$(CoreCLRCrossTargetComponentDirName)_$(TargetArchitecture)/native</TargetPath>
@@ -188,6 +191,7 @@
         $(LibrariesNativeArtifactsPath)*.so;
         $(LibrariesNativeArtifactsPath)*.dbg;
         $(LibrariesNativeArtifactsPath)*.dwarf;
+        $(LibrariesNativeArtifactsPath)*.dSYM;
         $(LibrariesNativeArtifactsPath)*.pdb"
         IsNative="true"
         Exclude="@(ExcludeNativeLibrariesRuntimeFiles)" />
diff --git a/eng/native/functions.cmake b/eng/native/functions.cmake
index 543722a9c0a59e..a0ac400cf2c835 100644
--- a/eng/native/functions.cmake
+++ b/eng/native/functions.cmake
@@ -369,7 +369,8 @@ endfunction()
 function (get_symbol_file_name targetName outputSymbolFilename)
   if (CLR_CMAKE_HOST_UNIX)
     if (CLR_CMAKE_TARGET_APPLE)
-      set(strip_destination_file $<TARGET_FILE:${targetName}>.dwarf)
+      # set(strip_destination_file $<TARGET_FILE:${targetName}>.dwarf)
+      set(strip_destination_file $<TARGET_FILE:${targetName}>.dSYM)
     else ()
       set(strip_destination_file $<TARGET_FILE:${targetName}>.dbg)
     endif ()
@@ -416,7 +417,8 @@ function(strip_symbols targetName outputFilename)
         OUTPUT_VARIABLE DSYMUTIL_HELP_OUTPUT
       )
 
-      set(DSYMUTIL_OPTS "--flat")
+      # set(DSYMUTIL_OPTS "--flat")
+      set(DSYMUTIL_OPTS "")
       if ("${DSYMUTIL_HELP_OUTPUT}" MATCHES "--minimize")
         list(APPEND DSYMUTIL_OPTS "--minimize")
       endif ()
diff --git a/eng/native/naming.props b/eng/native/naming.props
index b50c0c131cda5e..0aef054a27a252 100644
--- a/eng/native/naming.props
+++ b/eng/native/naming.props
@@ -18,7 +18,8 @@
         <LibPrefix>lib</LibPrefix>
         <LibSuffix>.dylib</LibSuffix>
         <StaticLibSuffix>.a</StaticLibSuffix>
-        <SymbolsSuffix>.dwarf</SymbolsSuffix>
+        <!-- <SymbolsSuffix>.dwarf</SymbolsSuffix> -->
+        <SymbolsSuffix>.dSYM</SymbolsSuffix>
       </PropertyGroup>
     </When>
     <Otherwise>
diff --git a/src/coreclr/.nuget/Directory.Build.targets b/src/coreclr/.nuget/Directory.Build.targets
index 379fbd65030b32..f81ddf85efc50d 100644
--- a/src/coreclr/.nuget/Directory.Build.targets
+++ b/src/coreclr/.nuget/Directory.Build.targets
@@ -47,7 +47,8 @@
       <NonWindowsNativeFile Include="@(NativeWithSymbolFile)"
                             Exclude="@(WindowsNativeFile)" />
 
-      <NonWindowsSymbolFile Include="@(NonWindowsNativeFile -> '%(Identity)$(SymbolsSuffix)')" />
+      <NonWindowsSymbolFile Condition="'$(SymbolsSuffix)'=='.dSYM'" Include="@(NonWindowsNativeFile -> '%(Identity)$(SymbolsSuffix)/**')" />
+      <NonWindowsSymbolFile Condition="'$(SymbolsSuffix)'!='.dSYM'" Include="@(NonWindowsNativeFile -> '%(Identity)$(SymbolsSuffix)')" />
 
       <ExistingWindowsSymbolFile Include="@(WindowsSymbolFile)" Condition="Exists('%(Identity)')" />
       <ExistingNonWindowsSymbolFile Include="@(NonWindowsSymbolFile)" Condition="Exists('%(Identity)') AND '$(SkipPackagingXplatSymbols)'!='true'" />
diff --git a/src/coreclr/nativeaot/BuildIntegration/Microsoft.NETCore.Native.targets b/src/coreclr/nativeaot/BuildIntegration/Microsoft.NETCore.Native.targets
index 74c2b457b9ad85..69d06b56bbdad3 100644
--- a/src/coreclr/nativeaot/BuildIntegration/Microsoft.NETCore.Native.targets
+++ b/src/coreclr/nativeaot/BuildIntegration/Microsoft.NETCore.Native.targets
@@ -71,7 +71,7 @@ The .NET Foundation licenses this file to you under the MIT license.
     <NativeBinaryExt Condition="'$(IsNativeExecutable)' != 'true' and '$(_targetOS)' == 'win' and '$(NativeLib)' == 'Static'">.lib</NativeBinaryExt>
     <NativeBinaryExt Condition="'$(IsNativeExecutable)' != 'true' and '$(_targetOS)' != 'win' and '$(NativeLib)' == 'Static'">.a</NativeBinaryExt>
 
-    <NativeSymbolExt Condition="'$(NativeSymbolExt)' == '' and '$(_IsApplePlatform)' == 'true'">.dsym</NativeSymbolExt>
+    <NativeSymbolExt Condition="'$(NativeSymbolExt)' == '' and '$(_IsApplePlatform)' == 'true'">.dSYM</NativeSymbolExt>
     <NativeSymbolExt Condition="'$(NativeSymbolExt)' == '' and '$(_targetOS)' == 'win'">.pdb</NativeSymbolExt>
     <NativeSymbolExt Condition="'$(NativeSymbolExt)' == ''">.dbg</NativeSymbolExt>
 
diff --git a/src/coreclr/tools/aot/crossgen2/crossgen2_publish.csproj b/src/coreclr/tools/aot/crossgen2/crossgen2_publish.csproj
index 8243494d1e15ad..6a8fd4061efcbf 100644
--- a/src/coreclr/tools/aot/crossgen2/crossgen2_publish.csproj
+++ b/src/coreclr/tools/aot/crossgen2/crossgen2_publish.csproj
@@ -51,8 +51,8 @@
     <IlcFrameworkNativePath>$(MicrosoftNetCoreAppRuntimePackNativeDir)</IlcFrameworkNativePath>
     <TrimmerSingleWarn>false</TrimmerSingleWarn>
     <!-- Use .dwarf files instead of .dsym files since our symbol exporting may not safely handle folders. -->
-    <NativeSymbolExt Condition="'$(_IsApplePlatform)' == 'true'">.dwarf</NativeSymbolExt>
-    <DsymUtilOptions Condition="'$(_IsApplePlatform)' == 'true'">--flat</DsymUtilOptions>
+    <!-- <NativeSymbolExt Condition="'$(_IsApplePlatform)' == 'true'">.dwarf</NativeSymbolExt> -->
+    <!-- <DsymUtilOptions Condition="'$(_IsApplePlatform)' == 'true'">--flat</DsymUtilOptions> -->
   </PropertyGroup>
 
   <ItemGroup Condition="'$(NativeAotSupported)' == 'true'">
diff --git a/src/libraries/System.IO.Ports/pkg/runtime.native.System.IO.Ports.props b/src/libraries/System.IO.Ports/pkg/runtime.native.System.IO.Ports.props
index 8ee8a9c20d8d7b..fa22d7d51298fa 100644
--- a/src/libraries/System.IO.Ports/pkg/runtime.native.System.IO.Ports.props
+++ b/src/libraries/System.IO.Ports/pkg/runtime.native.System.IO.Ports.props
@@ -20,8 +20,14 @@
   </ItemGroup>
 
   <Target Name="AddRuntimeSpecificNativeSymbolToPackage">
+    <ItemGroup Condition="'$(SymbolsSuffix)'!='.dSYM'">
+      <TfmSpecificDebugSymbolsFiles Include="$(NativeBinDir)$(LibPrefix)System.IO.Ports.Native$(LibSuffix)$(SymbolsSuffix)" />
+    </ItemGroup>
+    <ItemGroup Condition="'$(SymbolsSuffix)'=='.dSYM'">
+      <TfmSpecificDebugSymbolsFiles Include="$(NativeBinDir)$(LibPrefix)System.IO.Ports.Native$(LibSuffix)$(SymbolsSuffix)/**" />
+    </ItemGroup>
     <ItemGroup>
-      <TfmSpecificDebugSymbolsFile Include="$(NativeBinDir)$(LibPrefix)System.IO.Ports.Native$(LibSuffix)$(SymbolsSuffix)"
+      <TfmSpecificDebugSymbolsFile Include="@(TfmSpecificDebugSymbolsFiles)"
                                    TargetPath="/runtimes/$(OutputRID)/native"
                                    TargetFramework="$(TargetFramework)" />
     </ItemGroup>
diff --git a/src/native/corehost/corehost.proj b/src/native/corehost/corehost.proj
index 026cff6928567d..7b87dffd59e8e2 100644
--- a/src/native/corehost/corehost.proj
+++ b/src/native/corehost/corehost.proj
@@ -56,7 +56,12 @@
           Command="&quot;$(DotNetTool)&quot; exec @(InjectResourceTool) --bin &quot;$(DacPath)&quot; --image &quot;$(SingleFileHostDestinationPath)&quot; --name MINIDUMP_EMBEDDED_AUXILIARY_PROVIDER" />
 
     <!-- Copy symbols if they exist. We may not have separate symbols if they were not stripped from the native binary itself. -->
-    <Copy SourceFiles="$(SingleFileHostSymbolsPath)" DestinationFiles="$(SingleFileHostSymbolsDestinationPath)" Condition="Exists('$(SingleFileHostSymbolsPath)')" />
+    <ItemGroup Condition="'$(SymbolsSuffix)'=='.dSYM'">
+      <DSYMFiles Include="$(SingleFileHostSymbolsPath)/**/*"/>
+    </ItemGroup>
+
+    <Copy SourceFiles="@(DSYMFiles)" DestinationFolder="$(SingleFileHostSymbolsDestinationPath)/%(RecursiveDir)" Condition="'$(SymbolsSuffix)'=='.dSYM' and Exists('$(SingleFileHostSymbolsPath)')" />
+    <Copy SourceFiles="$(SingleFileHostSymbolsPath)" DestinationFiles="$(SingleFileHostSymbolsDestinationPath)" Condition="'$(SymbolsSuffix)'!='.dSYM' and Exists('$(SingleFileHostSymbolsPath)')" />
   </Target>
 
   <Target Name="PrepareSingleFileHostWithEmbeddedDac"