diff --git a/src/Xamarin.Android.Build.Tasks/Microsoft.Android.Sdk/targets/Microsoft.Android.Sdk.AssemblyResolution.targets b/src/Xamarin.Android.Build.Tasks/Microsoft.Android.Sdk/targets/Microsoft.Android.Sdk.AssemblyResolution.targets
index 47faa397635..e0f64889336 100644
--- a/src/Xamarin.Android.Build.Tasks/Microsoft.Android.Sdk/targets/Microsoft.Android.Sdk.AssemblyResolution.targets
+++ b/src/Xamarin.Android.Build.Tasks/Microsoft.Android.Sdk/targets/Microsoft.Android.Sdk.AssemblyResolution.targets
@@ -33,6 +33,10 @@ _ResolveAssemblies MSBuild target.
       <IntermediateAssembly Remove="@(IntermediateAssembly)" />
       <IntermediateAssembly Include="$(_OuterIntermediateAssembly)" />
     </ItemGroup>
+    <ItemGroup Condition=" '@(_DebugSymbolsIntermediatePath->Count())' != '0' ">
+      <_DebugSymbolsIntermediatePath Remove="@(_DebugSymbolsIntermediatePath)" />
+      <_DebugSymbolsIntermediatePath Include="$([System.IO.Path]::ChangeExtension ($(_OuterIntermediateAssembly), '.pdb'))" />
+    </ItemGroup>
   </Target>
 
   <Target Name="_ResolveAssemblies">
@@ -67,8 +71,8 @@ _ResolveAssemblies MSBuild target.
         Condition=" '%(Identity)' != '' "
     />
     <ProcessAssemblies
-        InputAssemblies="@(_ResolvedAssemblyFiles)"
-        ResolvedSymbols="@(_ResolvedSymbolFiles)"
+        InputAssemblies="@(_ResolvedAssemblyFiles->Distinct())"
+        ResolvedSymbols="@(_ResolvedSymbolFiles->Distinct())"
         IncludeDebugSymbols="$(AndroidIncludeDebugSymbols)"
         LinkMode="$(AndroidLinkMode)">
       <Output TaskParameter="OutputAssemblies" ItemName="_ProcessedAssemblies" />
@@ -121,10 +125,10 @@ _ResolveAssemblies MSBuild target.
   <Target Name="_PrepareAssemblies"
       DependsOnTargets="$(_PrepareAssembliesDependsOnTargets)">
     <ItemGroup Condition=" '$(AndroidLinkMode)' == 'None' And '$(AndroidIncludeDebugSymbols)' == 'true'  ">
-      <_ResolvedAssemblies          Include="@(ResolvedAssemblies->'$(MonoAndroidIntermediateAssemblyDir)%(DestinationSubPath)')" />
-      <_ResolvedUserAssemblies      Include="@(ResolvedUserAssemblies->'$(MonoAndroidIntermediateAssemblyDir)%(DestinationSubPath)')" />
-      <_ResolvedFrameworkAssemblies Include="@(ResolvedFrameworkAssemblies->'$(MonoAndroidIntermediateAssemblyDir)%(DestinationSubPath)')" />
-      <_ResolvedSymbols             Include="@(ResolvedSymbols->'$(MonoAndroidIntermediateAssemblyDir)%(DestinationSubPath)')" />
+      <_ResolvedAssemblies          Include="@(ResolvedAssemblies->'$(MonoAndroidIntermediateAssemblyDir)%(DestinationSubPath)')"          Condition=" '%(DestinationSubPath)' != '' " />
+      <_ResolvedUserAssemblies      Include="@(ResolvedUserAssemblies->'$(MonoAndroidIntermediateAssemblyDir)%(DestinationSubPath)')"      Condition=" '%(DestinationSubPath)' != '' " />
+      <_ResolvedFrameworkAssemblies Include="@(ResolvedFrameworkAssemblies->'$(MonoAndroidIntermediateAssemblyDir)%(DestinationSubPath)')" Condition=" '%(DestinationSubPath)' != '' " />
+      <_ResolvedSymbols             Include="@(ResolvedSymbols->'$(MonoAndroidIntermediateAssemblyDir)%(DestinationSubPath)')"             Condition=" '%(DestinationSubPath)' != '' " />
       <_ShrunkAssemblies            Include="@(_ResolvedAssemblies)" />
       <_ShrunkUserAssemblies        Include="@(_ResolvedUserAssemblies)" />
       <_ShrunkFrameworkAssemblies   Include="@(_ResolvedFrameworkAssemblies)" />
diff --git a/src/Xamarin.Android.Build.Tasks/Tasks/ProcessAssemblies.cs b/src/Xamarin.Android.Build.Tasks/Tasks/ProcessAssemblies.cs
index a400eb9b3c3..56643f355eb 100644
--- a/src/Xamarin.Android.Build.Tasks/Tasks/ProcessAssemblies.cs
+++ b/src/Xamarin.Android.Build.Tasks/Tasks/ProcessAssemblies.cs
@@ -66,12 +66,7 @@ public override bool RunTask ()
 						assembly.SetMetadata ("FrameworkAssembly", frameworkAssembly.ToString ());
 						assembly.SetMetadata ("HasMonoAndroidReference", MonoAndroidHelper.HasMonoAndroidReference (reader).ToString ());
 					} else {
-						Log.LogDebugMessage ($"Removing duplicate: {assembly.ItemSpec}");
-
-						var symbolPath = Path.ChangeExtension (assembly.ItemSpec, ".pdb");
-						if (symbols.Remove (symbolPath)) {
-							Log.LogDebugMessage ($"Removing duplicate: {symbolPath}");
-						}
+						symbols.Remove (Path.ChangeExtension (assembly.ItemSpec, ".pdb"));
 					}
 				}
 			}
diff --git a/src/Xamarin.Android.Build.Tasks/Tests/Xamarin.Android.Build.Tests/XASdkTests.cs b/src/Xamarin.Android.Build.Tasks/Tests/Xamarin.Android.Build.Tests/XASdkTests.cs
index b76e6c99e96..033a77641b5 100644
--- a/src/Xamarin.Android.Build.Tasks/Tests/Xamarin.Android.Build.Tests/XASdkTests.cs
+++ b/src/Xamarin.Android.Build.Tasks/Tests/Xamarin.Android.Build.Tests/XASdkTests.cs
@@ -359,14 +359,16 @@ public void DotNetBuild (string runtimeIdentifiers, bool isRelease)
 			var apkPath = Path.Combine (outputPath, "UnnamedProject.UnnamedProject.apk");
 			FileAssert.Exists (apkPath);
 			using (var apk = ZipHelper.OpenZip (apkPath)) {
+				apk.AssertContainsEntry (apkPath, $"assemblies/{proj.ProjectName}.dll", shouldContainEntry: expectEmbeddedAssembies);
+				apk.AssertContainsEntry (apkPath, $"assemblies/{proj.ProjectName}.pdb", shouldContainEntry: !CommercialBuildAvailable && !isRelease);
 				var rids = runtimeIdentifiers.Split (';');
 				foreach (var abi in rids.Select (MonoAndroidHelper.RuntimeIdentifierToAbi)) {
 					apk.AssertContainsEntry (apkPath, $"lib/{abi}/libmonodroid.so");
 					apk.AssertContainsEntry (apkPath, $"lib/{abi}/libmonosgen-2.0.so");
 					if (rids.Length > 1) {
-						apk.AssertContainsEntry (apkPath, $"assemblies/{abi}/System.Private.CoreLib.dll", expectEmbeddedAssembies);
+						apk.AssertContainsEntry (apkPath, $"assemblies/{abi}/System.Private.CoreLib.dll", shouldContainEntry: expectEmbeddedAssembies);
 					} else {
-						apk.AssertContainsEntry (apkPath, "assemblies/System.Private.CoreLib.dll", expectEmbeddedAssembies);
+						apk.AssertContainsEntry (apkPath, "assemblies/System.Private.CoreLib.dll", shouldContainEntry: expectEmbeddedAssembies);
 					}
 				}
 			}