diff --git a/build/Branding.props b/build/Branding.props
index 9a66fdc2d..7b126782e 100644
--- a/build/Branding.props
+++ b/build/Branding.props
@@ -21,14 +21,14 @@
     <HostMonikerRid Condition=" '$(HostMonikerRid)' == '' ">$(HostOSName)-$(Architecture)</HostMonikerRid>
 
     <ArtifactNameSdk>dotnet-sdk-internal</ArtifactNameSdk>
-    <ArtifactNameSdkDebug>dotnet-sdk-debug</ArtifactNameSdkDebug>
+    <ArtifactNameSdkSymbols>dotnet-sdk-symbols</ArtifactNameSdkSymbols>
     <ArtifactNameCombinedHostHostFxrFrameworkSdk>dotnet-sdk</ArtifactNameCombinedHostHostFxrFrameworkSdk>
     <ArtifactNameSdkLanguagePack>$(ArtifactNameCombinedHostHostFxrFrameworkSdk)-langpack</ArtifactNameSdkLanguagePack>
 
     <ArtifactNameWithVersionSdk>$(ArtifactNameSdk)-$(SdkVersion)-$(ProductMonikerRid)</ArtifactNameWithVersionSdk>
     <ArtifactNameWithVersionMSBuildExtensions>dotnet-standard-support-vs2015-$(SdkVersion)-$(ProductMonikerRid)</ArtifactNameWithVersionMSBuildExtensions>
 
-    <ArtifactNameWithVersionSdkDebug>$(ArtifactNameSdkDebug)-$(SdkVersion)-$(ProductMonikerRid)</ArtifactNameWithVersionSdkDebug>
+    <ArtifactNameWithVersionSdkSymbols>$(ArtifactNameSdkSymbols)-$(SdkVersion)-$(ProductMonikerRid)</ArtifactNameWithVersionSdkSymbols>
     <ArtifactNameWithVersionCombinedHostHostFxrFrameworkSdk>$(ArtifactNameCombinedHostHostFxrFrameworkSdk)-$(SdkVersion)-$(ProductMonikerRid)</ArtifactNameWithVersionCombinedHostHostFxrFrameworkSdk>
     <ArtifactNameWithVersionSdkLanguagePack>$(ArtifactNameSdkLanguagePack)-$(SdkVersion)-$(ProductMonikerRid)</ArtifactNameWithVersionSdkLanguagePack>
     <DistroSpecificArtifactNameWithVersionCombinedHostHostFxrFrameworkSdk>$(ArtifactNameCombinedHostHostFxrFrameworkSdk)-$(SdkVersion)-$(HostMonikerRid)</DistroSpecificArtifactNameWithVersionCombinedHostHostFxrFrameworkSdk>
diff --git a/build/package/Layout.targets b/build/package/Layout.targets
index 8d37a5b36..4c14f6ee3 100644
--- a/build/package/Layout.targets
+++ b/build/package/Layout.targets
@@ -1,7 +1,7 @@
 <?xml version="1.0" encoding="utf-8"?>
 <Project ToolsVersion="14.0" xmlns="http://schemas.microsoft.com/developer/msbuild/2003">
   <PropertyGroup>
-    <SdkDebugLayoutOutputDirectory>$(LayoutDirectory)/$(ArtifactNameSdkDebug)</SdkDebugLayoutOutputDirectory>
+    <SdkSymbolsLayoutOutputDirectory>$(LayoutDirectory)/$(ArtifactNameSdkSymbols)</SdkSymbolsLayoutOutputDirectory>
     <CombinedHostHostFxrFrameworkSdkOutputDirectory>$(LayoutDirectory)/$(ArtifactNameCombinedHostHostFxrFrameworkSdk)</CombinedHostHostFxrFrameworkSdkOutputDirectory>
     <SdkLanguagePackOutputDirectory>$(LayoutDirectory)/$(ArtifactNameSdkLanguagePack)</SdkLanguagePackOutputDirectory>
     <SatelliteAssemblies>*.resources.dll</SatelliteAssemblies>
@@ -12,7 +12,7 @@
     <!-- Set up Items with Layout Input Files -->
     <ItemGroup>
       <SdkLayoutInput Include="$(OutputDirectory)/sdk/**/*" />
-      <SdkDebugLayoutInput Include="$(SymbolsDirectory)/sdk/**/*" />
+      <SdkSymbolsLayoutInput Include="$(SymbolsDirectory)/sdk/**/*" />
       <CombinedHostHostFxrFrameworkSdkInput Include="$(OutputDirectory)/**/*" />
       <SdkLanguagePackInput Include="$(OutputDirectory)/sdk/**/$(SatelliteAssemblies)" />
 
@@ -30,9 +30,10 @@
       <Output TaskParameter="RelativePath" ItemName="SdkRelativeOutputFiles" />
     </MakeRelative>
     <MakeRelative
-      Path1="$(SymbolsDirectory)"
-      Path2="%(SdkDebugLayoutInput.Identity)" >
-      <Output TaskParameter="RelativePath" ItemName="SdkDebugRelativeOutputFiles" />
+      Condition="'$(SeparateSymbolsArchive)' != 'false'"
+      Path1="$(SymbolsDirectory)/"
+      Path2="%(SdkSymbolsLayoutInput.Identity)" >
+      <Output TaskParameter="RelativePath" ItemName="SdkSymbolsRelativeOutputFiles" />
     </MakeRelative>
     <MakeRelative
       Path1="$(OutputDirectory)/"
@@ -70,11 +71,11 @@
         <Name>$(ArtifactNameSdk)</Name>
       </LayoutDefinition>
 
-      <LayoutDefinition Include="Debug">
-        <InputFiles>@(SdkDebugLayoutInput)</InputFiles>
-        <OutputFiles>@(SdkDebugRelativeOutputFiles -> '$(SdkDebugLayoutOutputDirectory)/%(Identity)')</OutputFiles>
-        <NameWithVersion>$(ArtifactNameWithVersionSdkDebug)</NameWithVersion>
-        <Name>$(ArtifactNameSdkDebug)</Name>
+      <LayoutDefinition Include="SdkSymbols" Condition="'$(SeparateSymbolsArchive)' != 'false'">
+        <InputFiles>@(SdkSymbolsLayoutInput)</InputFiles>
+        <OutputFiles>@(SdkSymbolsRelativeOutputFiles -> '$(SdkSymbolsLayoutOutputDirectory)/%(Identity)')</OutputFiles>
+        <NameWithVersion>$(ArtifactNameWithVersionSdkSymbols)</NameWithVersion>
+        <Name>$(ArtifactNameSdkSymbols)</Name>
       </LayoutDefinition>
 
       <LayoutDefinition Include="CombinedHostHostFxrFrameworkSdk">
diff --git a/build_projects/dotnet-cli-build/Crossgen.cs b/build_projects/dotnet-cli-build/Crossgen.cs
index 68129a065..48ebdebfa 100644
--- a/build_projects/dotnet-cli-build/Crossgen.cs
+++ b/build_projects/dotnet-cli-build/Crossgen.cs
@@ -3,7 +3,9 @@
 // See the LICENSE file in the project root for more information.
 
 using System;
+using System.Diagnostics;
 using System.IO;
+using System.Runtime.InteropServices;
 using Microsoft.Build.Framework;
 using Microsoft.Build.Utilities;
 
@@ -22,12 +24,18 @@ namespace Microsoft.DotNet.Build.Tasks
 
         public string CrossgenPath { get; set; }
 
+        public bool CreateSymbols { get; set; }
+
+        public string DiasymReaderPath { get; set; }
+
         public bool ReadyToRun { get; set; }
 
         public ITaskItem[] PlatformAssemblyPaths { get; set; }
 
         private string TempOutputPath { get; set; }
 
+        private bool _secondInvocationToCreateSymbols;
+
         protected override bool ValidateParameters()
         {
             base.ValidateParameters();
@@ -58,6 +66,12 @@ namespace Microsoft.DotNet.Build.Tasks
                 File.Delete(TempOutputPath);
             }
 
+            if (toolResult && CreateSymbols)
+            {
+                _secondInvocationToCreateSymbols = true;
+                toolResult = base.Execute();
+            }
+
             return toolResult;
         }
 
@@ -83,9 +97,30 @@ namespace Microsoft.DotNet.Build.Tasks
 
         protected override string GenerateCommandLineCommands()
         {
+            if (_secondInvocationToCreateSymbols)
+            {
+                return $"{GetReadyToRun()} {GetPlatformAssemblyPaths()} {GetDiasymReaderPath()} {GetCreateSymbols()}";
+            }
+
             return $"{GetReadyToRun()} {GetInPath()} {GetOutPath()} {GetPlatformAssemblyPaths()} {GetJitPath()}";
         }
 
+        private string GetCreateSymbols()
+        {
+            var option = RuntimeInformation.IsOSPlatform(OSPlatform.Windows) ? "-createpdb" : "-createperfmap";
+            return $"{option} \"{Path.GetDirectoryName(DestinationPath)}\" \"{DestinationPath}\"";
+        }
+
+        private string GetDiasymReaderPath()
+        {
+            if (string.IsNullOrEmpty(DiasymReaderPath))
+            {
+                return null;
+            }
+
+            return $"-diasymreaderpath \"{DiasymReaderPath}\"";
+        }
+
         private string GetReadyToRun()
         {
             if (ReadyToRun)
diff --git a/src/redist/redist.csproj b/src/redist/redist.csproj
index c45cd6bdf..b8e179c3b 100644
--- a/src/redist/redist.csproj
+++ b/src/redist/redist.csproj
@@ -101,7 +101,8 @@
 
     <Delete Files="$(PublishDir)/$(TargetName).deps.json;
                    $(PublishDir)/$(TargetName).runtimeconfig.json;
-                   $(PublishDir)/%(BundledToolProjects.Identity).dll" />
+                   $(PublishDir)/%(BundledToolProjects.Identity).dll;
+                   $(PublishDir)/%(BundledToolProjects.Identity).pdb" />
 
     <ChangeEntryPointLibraryName
           DepsFile="$(PublishDir)/%(BundledTools.Identity).deps.json"
@@ -198,7 +199,7 @@
 
   <Target Name="CrossgenPublishDir"
           Condition=" '$(DISABLE_CROSSGEN)' == '' "
-          AfterTargets="PublishMSBuildExtensions">
+          AfterTargets="GenerateCliRuntimeConfigurationFiles">
     <ItemGroup>
       <!-- Removing Full CLR built TestHost assemblies from getting Crossgen as it is throwing error -->
       <SdkFiles Include="$(PublishDir)/**/*" Exclude="$(PublishDir)/TestHost*/**/*;$(PublishDir)/Sdks/**/*" />
@@ -208,6 +209,11 @@
 
       <!-- Don't try to CrossGen tasks and supporting DLLs compiled for .NET Framework -->
       <SdkFiles Remove="$(PublishDir)/Microsoft\Microsoft.NET.Build.Extensions\tools\net*\**\*" />
+
+      <!-- Don't crossgen satellite assemblies -->
+      <SdkFiles Remove="$(PublishDir)/**/*.resources.dll" />
+
+      <DiasymReaderPath Include="$(SharedFrameworkNameVersionPath)/Microsoft.DiaSymReader.Native.*.dll" />
     </ItemGroup>
 
     <AddMetadataIsPE Items="@(SdkFiles)">
@@ -227,11 +233,19 @@
            Glob="$(CrossgenPath)"
            Mode="u+x" />
 
+    <!-- Crossgen does not support generating symbols on Mac  -->
+    <PropertyGroup Condition="'$(CreateCrossgenSymbols)' == ''">
+      <CreateCrossgenSymbols>true</CreateCrossgenSymbols>
+      <CreateCrossgenSymbols Condition="'$(OSName)' == 'osx'">false</CreateCrossgenSymbols>
+   </PropertyGroup>
+
     <Crossgen SourceAssembly="%(CrossgenTargets.FullPath)"
               DestinationPath="%(CrossgenTargets.FullPath)"
               JITPath="$(LibCLRJitPath)"
               CrossgenPath="$(CrossgenPath)"
               ReadyToRun="True"
+              CreateSymbols="$(CreateCrossgenSymbols)"
+              DiasymReaderPath="@(DiasymReaderPath)"
               PlatformAssemblyPaths="@(PlatformAssemblies);
                                      @(PublishDirSubDirectories);
                                      $(SharedFrameworkNameVersionPath)" />
@@ -248,23 +262,16 @@
     <Chmod Mode="755" Glob="$(SdkOutputDirectory)/FSharp/RunFsc.sh" />
   </Target>
 
-  <Target Name="CreateSymbolsDirectory"
-          AfterTargets="CrossgenPublishDir">
+  <Target Name="SeparateSymbolsFromPublishDir"
+          AfterTargets="CrossgenPublishDir"
+          Condition="'$(SeparateSymbolsArchive)' != 'false'">
     <ItemGroup>
-      <_AllSdkFiles Include="$(PublishDir)/**/*" />
+      <PdbsToMove Include="$(PublishDir)/**/*.pdb" />
+      <PdbsToMove Include="$(PublishDir)/**/*.ni.*.map" />
     </ItemGroup>
 
-    <Copy SourceFiles="@(_AllSdkFiles)"
-        DestinationFiles="@(_AllSdkFiles->'$(SymbolsDirectory)/sdk/%(RecursiveDir)%(Filename)%(Extension)')" />
-  </Target>
-
-  <Target Name="RemovePdbsFromPublishDir"
-          AfterTargets="CreateSymbolsDirectory">
-    <ItemGroup>
-      <PdbsToClean Include="$(PublishDir)/**/*.pdb" />
-    </ItemGroup>
-
-    <Delete Files="@(PdbsToClean)" />
+    <Move SourceFiles="@(PdbsToMove)" 
+          DestinationFiles="@(PdbsToMove->'$(SymbolsDirectory)/sdk/$(SdkVersion)/%(RecursiveDir)%(Filename)%(Extension)')" />
   </Target>
 
   <Target Name="PublishStage2WithBackwardsCompatibleRuntimes"
@@ -285,6 +292,7 @@
   </Target>
 
   <Target Name="RetargetVSTestConsole"
+          BeforeTargets="PublishStage2WithBackwardsCompatibleRuntimes"
           AfterTargets="Publish">
     <PropertyGroup>
       <VSTestRuntimeConfigPath>$(PublishDir)/vstest.console.runtimeconfig.json</VSTestRuntimeConfigPath>