diff --git a/test/ServerComparison.FunctionalTests/HelloWorldTest.cs b/test/ServerComparison.FunctionalTests/HelloWorldTest.cs
index 35e84bc492..37916008fb 100644
--- a/test/ServerComparison.FunctionalTests/HelloWorldTest.cs
+++ b/test/ServerComparison.FunctionalTests/HelloWorldTest.cs
@@ -17,28 +17,31 @@ namespace ServerComparison.FunctionalTests
     public class HelloWorldTests
     {
         [ConditionalTheory]
-        [OSSkipCondition(OperatingSystems.Linux | OperatingSystems.MacOSX)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [InlineData(ServerType.IISExpress, RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "http://localhost:5061/")]
         [InlineData(ServerType.IISExpress, RuntimeFlavor.Clr, RuntimeArchitecture.x64, "http://localhost:5062/")]
         [InlineData(ServerType.WebListener, RuntimeFlavor.Clr, RuntimeArchitecture.x86, "http://localhost:5063/")]
         [InlineData(ServerType.WebListener, RuntimeFlavor.CoreClr, RuntimeArchitecture.x64, "http://localhost:5064/")]
+        [InlineData(ServerType.Kestrel, RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "http://localhost:5065/")]
+        [InlineData(ServerType.Kestrel, RuntimeFlavor.Clr, RuntimeArchitecture.x64, "http://localhost:5066/")]
         public Task HelloWorld_Windows(ServerType serverType, RuntimeFlavor runtimeFlavor, RuntimeArchitecture architecture, string applicationBaseUrl)
         {
             return HelloWorld(serverType, runtimeFlavor, architecture, applicationBaseUrl);
         }
 
         [Theory]
-        [InlineData(ServerType.Kestrel, RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "http://localhost:5065/")]
-        [InlineData(ServerType.Kestrel, RuntimeFlavor.Clr, RuntimeArchitecture.x64, "http://localhost:5066/")]
+        [OSSkipCondition(OperatingSystems.Windows)]
+        [InlineData(ServerType.Kestrel, RuntimeFlavor.CoreClr, RuntimeArchitecture.x64, "http://localhost:5067/")]
         public Task HelloWorld_Kestrel(ServerType serverType, RuntimeFlavor runtimeFlavor, RuntimeArchitecture architecture, string applicationBaseUrl)
         {
             return HelloWorld(serverType, runtimeFlavor, architecture, applicationBaseUrl);
         }
 
         [ConditionalTheory]
-        [FrameworkSkipCondition(RuntimeFrameworks.CLR)]
-        [InlineData(ServerType.Kestrel, RuntimeFlavor.Mono, RuntimeArchitecture.x86, "http://localhost:5067/")]
-        [InlineData(ServerType.Kestrel, RuntimeFlavor.Mono, RuntimeArchitecture.x64, "http://localhost:5068/")]
+        [OSSkipCondition(OperatingSystems.Windows)]
+        [InlineData(ServerType.Kestrel, RuntimeFlavor.Mono, RuntimeArchitecture.x86, "http://localhost:5068/")]
+        [InlineData(ServerType.Kestrel, RuntimeFlavor.Mono, RuntimeArchitecture.x64, "http://localhost:5069/")]
         public Task HelloWorld_Mono(ServerType serverType, RuntimeFlavor runtimeFlavor, RuntimeArchitecture architecture, string applicationBaseUrl)
         {
             return HelloWorld(serverType, runtimeFlavor, architecture, applicationBaseUrl);
@@ -46,7 +49,8 @@ namespace ServerComparison.FunctionalTests
 
         [ConditionalTheory]
         [SkipIfIISVariationsNotEnabled]
-        [OSSkipCondition(OperatingSystems.MacOSX | OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [SkipIfCurrentRuntimeIsCoreClr]
         [InlineData(ServerType.IIS, RuntimeFlavor.Clr, RuntimeArchitecture.x64, "http://localhost:5069/")]
         [InlineData(ServerType.IIS, RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "http://localhost:5070/")]