diff --git a/src/Xamarin.Android.Build.Tasks/Tasks/CreateMultiDexMainDexClassList.cs b/src/Xamarin.Android.Build.Tasks/Tasks/CreateMultiDexMainDexClassList.cs
index d2a21bd3ed5..745541847bf 100644
--- a/src/Xamarin.Android.Build.Tasks/Tasks/CreateMultiDexMainDexClassList.cs
+++ b/src/Xamarin.Android.Build.Tasks/Tasks/CreateMultiDexMainDexClassList.cs
@@ -75,31 +75,28 @@ protected override string GenerateCommandLineCommands ()
 
 		void GenerateProguardCommands (CommandLineBuilder cmd)
 		{
-			var enclosingChar = OS.IsWindows ? "\"" : string.Empty;
+			var enclosingChar = OS.IsWindows ? "\"" : "'";
 			var jars = JavaLibraries.Select (i => i.ItemSpec).Concat (new string [] { Path.Combine (ClassesOutputDirectory, "classes.zip") });
 			cmd.AppendSwitchIfNotNull ("-jar ", ProguardJarPath);
-			cmd.AppendSwitchUnquotedIfNotNull ("-injars ", $"{enclosingChar}'" + string.Join ($"{ProguardInputJarFilter}'{Path.PathSeparator}'", jars) + $"{ProguardInputJarFilter}'{enclosingChar}");
+			cmd.AppendSwitchUnquotedIfNotNull ("-injars ", $"{enclosingChar}" + string.Join ($"{ProguardInputJarFilter}{enclosingChar}{Path.PathSeparator}{enclosingChar}", jars) + $"{ProguardInputJarFilter}{enclosingChar}");
 			cmd.AppendSwitch ("-dontwarn");
 			cmd.AppendSwitch ("-forceprocessing");
 			cmd.AppendSwitchIfNotNull ("-outjars ", tempJar);
-			cmd.AppendSwitchIfNotNull ("-libraryjars ", $"'{Path.Combine (AndroidSdkBuildToolsPath, "lib", "shrinkedAndroid.jar")}'");
+			cmd.AppendSwitchIfNotNull ("-libraryjars ", $"{enclosingChar}{Path.Combine (AndroidSdkBuildToolsPath, "lib", "shrinkedAndroid.jar")}{enclosingChar}");
 			cmd.AppendSwitch ("-dontoptimize");
 			cmd.AppendSwitch ("-dontobfuscate");
 			cmd.AppendSwitch ("-dontpreverify");
-			cmd.AppendSwitchUnquotedIfNotNull ("-include ", $"{enclosingChar}'{Path.Combine (AndroidSdkBuildToolsPath, "mainDexClasses.rules")}'{enclosingChar}");
+			cmd.AppendSwitchUnquotedIfNotNull ("-include ", $"{enclosingChar}{Path.Combine (AndroidSdkBuildToolsPath, "mainDexClasses.rules")}{enclosingChar}");
 		}
 
 		void GenerateMainDexListBuilderCommands(CommandLineBuilder cmd)
 		{
-			var enclosingDoubleQuote = OS.IsWindows ? "\"" : string.Empty;
-			var enclosingQuote = OS.IsWindows ? string.Empty : "'";
+			var enclosingChar = OS.IsWindows ? "\"" : "'";
 			var jars = JavaLibraries.Select (i => i.ItemSpec).Concat (new string [] { Path.Combine (ClassesOutputDirectory, "classes.zip") });
 			cmd.AppendSwitchIfNotNull ("-Djava.ext.dirs=", Path.Combine (AndroidSdkBuildToolsPath, "lib"));
 			cmd.AppendSwitch ("com.android.multidex.MainDexListBuilder");
-			cmd.AppendSwitch ($"{enclosingDoubleQuote}{tempJar}{enclosingDoubleQuote}");
-			cmd.AppendSwitchUnquotedIfNotNull ("", $"{enclosingDoubleQuote}{enclosingQuote}" +
-				string.Join ($"{enclosingQuote}{Path.PathSeparator}{enclosingQuote}", jars) + 
-				$"{enclosingQuote}{enclosingDoubleQuote}");
+			cmd.AppendSwitchUnquotedIfNotNull ("", $"{enclosingChar}{tempJar}{enclosingChar}");
+			cmd.AppendSwitchUnquotedIfNotNull ("", enclosingChar + string.Join ($"{enclosingChar}{Path.PathSeparator}{enclosingChar}", jars) + enclosingChar);
 			writeOutputToKeepFile = true;
 		}
 
diff --git a/src/Xamarin.Android.Build.Tasks/Tasks/Proguard.cs b/src/Xamarin.Android.Build.Tasks/Tasks/Proguard.cs
index 31f716edc09..29ed6b14a35 100644
--- a/src/Xamarin.Android.Build.Tasks/Tasks/Proguard.cs
+++ b/src/Xamarin.Android.Build.Tasks/Tasks/Proguard.cs
@@ -140,10 +140,10 @@ protected override string GenerateCommandLineCommands ()
 
 			var injars = new List<string> ();
 			var libjars = new List<string> ();
-			injars.Add (classesZip);
+			injars.Add (classesZip + ProguardInputJarFilter);
 			if (JavaLibrariesToEmbed != null)
 				foreach (var jarfile in JavaLibrariesToEmbed)
-					injars.Add (jarfile.ItemSpec);
+					injars.Add (jarfile.ItemSpec + ProguardInputJarFilter);
 
 			using (var xamcfg = File.Create (ProguardCommonXamarinConfiguration))
 				GetType ().Assembly.GetManifestResourceStream ("proguard_xamarin.cfg").CopyTo (xamcfg);
@@ -158,11 +158,11 @@ protected override string GenerateCommandLineCommands ()
 				.Select (s => s.Trim ())
 				.Where (s => !string.IsNullOrWhiteSpace (s));
 
-			var enclosingChar = OS.IsWindows ? "\"" : string.Empty;
+			var enclosingChar = OS.IsWindows ? "\"" : "'";
 
 			foreach (var file in configs) {
 				if (File.Exists (file))
-					cmd.AppendSwitchUnquotedIfNotNull ("-include ", $"{enclosingChar}'{file}'{enclosingChar}");
+					cmd.AppendSwitchUnquotedIfNotNull ("-include ", $"{enclosingChar}{file}{enclosingChar}");
 				else
 					Log.LogWarning ("Proguard configuration file '{0}' was not found.", file);
 			}
@@ -172,10 +172,9 @@ protected override string GenerateCommandLineCommands ()
 				foreach (var jarfile in ExternalJavaLibraries.Select (p => p.ItemSpec))
 					libjars.Add (jarfile);
 
-			cmd.AppendSwitchUnquotedIfNotNull ("-injars ", $"{enclosingChar}'" + string.Join ($"{ProguardInputJarFilter}'{Path.PathSeparator}'", injars.Distinct ()) + $"{ProguardInputJarFilter}'{enclosingChar}");
-
-			cmd.AppendSwitchUnquotedIfNotNull ("-libraryjars ", $"{enclosingChar}'" + string.Join ($"'{Path.PathSeparator}'", libjars.Distinct ()) + $"'{enclosingChar}");
-			
+			string delimiter = $"{enclosingChar}{Path.PathSeparator}{enclosingChar}";
+			cmd.AppendSwitchUnquotedIfNotNull ("-injars ", enclosingChar + string.Join (delimiter, injars.Distinct ()) + enclosingChar);
+			cmd.AppendSwitchUnquotedIfNotNull ("-libraryjars ", enclosingChar + string.Join (delimiter, libjars.Distinct ()) + enclosingChar);
 			cmd.AppendSwitchIfNotNull ("-outjars ", ProguardJarOutput);
 
 			if (EnableLogging) {
diff --git a/src/Xamarin.Android.Build.Tasks/Tests/Xamarin.Android.Build.Tests/BuildTest.cs b/src/Xamarin.Android.Build.Tasks/Tests/Xamarin.Android.Build.Tests/BuildTest.cs
index a30f1f963c6..d77afb397cb 100644
--- a/src/Xamarin.Android.Build.Tasks/Tests/Xamarin.Android.Build.Tests/BuildTest.cs
+++ b/src/Xamarin.Android.Build.Tasks/Tests/Xamarin.Android.Build.Tests/BuildTest.cs
@@ -1656,25 +1656,31 @@ public void BuildReleaseApplication ()
 		}
 
 		[Test]
-		public void BuildReleaseApplicationWithSpacesInPath ()
+		public void BuildApplicationWithSpacesInPath ([Values (true, false)] bool isRelease, [Values (true, false)] bool enableProguard, [Values (true, false)] bool enableMultiDex)
 		{
 			var proj = new XamarinAndroidApplicationProject () {
-				IsRelease = true,
-				AotAssemblies = true,
+				IsRelease = isRelease,
+				AotAssemblies = isRelease,
+				EnableProguard = enableProguard,
 			};
-			proj.Imports.Add (new Import ("foo.targets") {
-				TextContent = () => @"<?xml version=""1.0"" encoding=""utf-16""?>
+			if (enableMultiDex)
+				proj.SetProperty ("AndroidEnableMultiDex", "True");
+
+			if (isRelease) {
+				proj.Imports.Add (new Import ("foo.targets") {
+					TextContent = () => @"<?xml version=""1.0"" encoding=""utf-16""?>
 <Project ToolsVersion=""4.0"" xmlns=""http://schemas.microsoft.com/developer/msbuild/2003"">
 <Target Name=""_Foo"" AfterTargets=""_SetLatestTargetFrameworkVersion"">
 	<PropertyGroup>
-		<AotAssemblies Condition=""!Exists('$(MonoAndroidBinDirectory)"+ Path.DirectorySeparatorChar + @"cross-arm')"">False</AotAssemblies>
+		<AotAssemblies Condition=""!Exists('$(MonoAndroidBinDirectory)" + Path.DirectorySeparatorChar + @"cross-arm')"">False</AotAssemblies>
 	</PropertyGroup>
 	<Message Text=""$(AotAssemblies)"" />
 </Target>
 </Project>
 ",
-			});
-			using (var b = CreateApkBuilder (Path.Combine ("temp", "BuildReleaseAppWithA InIt(1)"))) {
+				});
+			}
+			using (var b = CreateApkBuilder (Path.Combine ("temp", $"BuildReleaseAppWithA InIt({isRelease}{enableProguard}{enableMultiDex})"))) {
 				Assert.IsTrue (b.Build (proj), "Build should have succeeded.");
 			}
 		}
@@ -2209,6 +2215,7 @@ public void foo()
 			using (var builder = CreateApkBuilder (Path.Combine ("temp", TestContext.CurrentContext.Test.Name))) {
 				builder.ThrowOnBuildFailure = false;
 				Assert.AreEqual (enableDesugar, builder.Build (proj), "Unexpected build result");
+				Assert.IsFalse (builder.LastBuildOutput.ContainsText ("Duplicate zip entry"), "Should not get warning about [META-INF/MANIFEST.MF]");
 			}
 		}
 	}