diff --git a/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/HelloWorldTest.cs b/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/HelloWorldTest.cs
index 27eb3106c4..9514c887c7 100644
--- a/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/HelloWorldTest.cs
+++ b/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/HelloWorldTest.cs
@@ -17,7 +17,8 @@ namespace Microsoft.AspNet.IISPlatformHandler.FunctionalTests
     public class HelloWorldTests
     {
         [ConditionalTheory]
-        [OSSkipCondition(OperatingSystems.Linux | OperatingSystems.MacOSX)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [InlineData(RuntimeFlavor.Clr, RuntimeArchitecture.x86, "http://localhost:5061/", ServerType.Kestrel)]
         [InlineData(RuntimeFlavor.Clr, RuntimeArchitecture.x64, "http://localhost:5062/", ServerType.Kestrel)]
         [InlineData(RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "http://localhost:5063/", ServerType.Kestrel)]
@@ -28,7 +29,8 @@ namespace Microsoft.AspNet.IISPlatformHandler.FunctionalTests
         }
 
         [ConditionalTheory]
-        [OSSkipCondition(OperatingSystems.Linux | OperatingSystems.MacOSX)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [InlineData(RuntimeFlavor.Clr, RuntimeArchitecture.x86, "http://localhost:5065/", ServerType.Kestrel)]
         [InlineData(RuntimeFlavor.Clr, RuntimeArchitecture.x64, "http://localhost:5066/", ServerType.Kestrel)]
         [InlineData(RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "http://localhost:5067/", ServerType.Kestrel)]
@@ -40,7 +42,8 @@ namespace Microsoft.AspNet.IISPlatformHandler.FunctionalTests
 
         [ConditionalTheory]
         [SkipIfIISVariationsNotEnabled]
-        [OSSkipCondition(OperatingSystems.MacOSX | OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [SkipIfCurrentRuntimeIsCoreClr]
         [InlineData(RuntimeFlavor.Clr, RuntimeArchitecture.x64, "http://localhost:5069/", ServerType.Kestrel)]
         [InlineData(RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "http://localhost:5070/", ServerType.Kestrel)]
diff --git a/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/HttpsTest.cs b/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/HttpsTest.cs
index 5bb3760d04..9df614b099 100644
--- a/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/HttpsTest.cs
+++ b/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/HttpsTest.cs
@@ -18,7 +18,8 @@ namespace Microsoft.AspNet.IISPlatformHandler.FunctionalTests
     public class HttpsTest
     {
         [ConditionalTheory]
-        [OSSkipCondition(OperatingSystems.MacOSX | OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [InlineData(RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "https://localhost:44399/")]
         [InlineData(RuntimeFlavor.Clr, RuntimeArchitecture.x64, "https://localhost:44398/")]
         public Task Https_HelloWorld(RuntimeFlavor runtimeFlavor, RuntimeArchitecture architecture, string applicationBaseUrl)
@@ -71,7 +72,8 @@ namespace Microsoft.AspNet.IISPlatformHandler.FunctionalTests
         }
 
         [ConditionalTheory]
-        [OSSkipCondition(OperatingSystems.MacOSX | OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [InlineData(RuntimeFlavor.CoreClr, RuntimeArchitecture.x64, "https://localhost:44397/")]
         [InlineData(RuntimeFlavor.Clr, RuntimeArchitecture.x86, "https://localhost:44396/")]
         public Task Https_HelloWorld_NoClientCert(RuntimeFlavor runtimeFlavor, RuntimeArchitecture architecture, string applicationBaseUrl)
@@ -80,7 +82,8 @@ namespace Microsoft.AspNet.IISPlatformHandler.FunctionalTests
         }
 
         [ConditionalTheory(Skip = "Manual test only, selecting a client cert is non-determanistic on different machines.")]
-        [OSSkipCondition(OperatingSystems.MacOSX | OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [InlineData(RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "https://localhost:44395/")]
         [InlineData(RuntimeFlavor.Clr, RuntimeArchitecture.x64, "https://localhost:44394/")]
         public Task Https_HelloWorld_ClientCert(RuntimeFlavor runtimeFlavor, RuntimeArchitecture architecture, string applicationBaseUrl)
diff --git a/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/NtlmAuthentationTest.cs b/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/NtlmAuthentationTest.cs
index 6402bc0718..04e281f84f 100644
--- a/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/NtlmAuthentationTest.cs
+++ b/test/Microsoft.AspNet.IISPlatformHandler.FunctionalTests/NtlmAuthentationTest.cs
@@ -19,7 +19,8 @@ namespace Microsoft.AspNet.IISPlatformHandler.FunctionalTests
     {
         // TODO: The middleware needs to implement auth handlers.
         [ConditionalTheory, Trait("ServerComparison.FunctionalTests", "ServerComparison.FunctionalTests")]
-        [OSSkipCondition(OperatingSystems.Linux | OperatingSystems.MacOSX)]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
         [InlineData(ServerType.IISExpress, RuntimeFlavor.CoreClr, RuntimeArchitecture.x86, "http://localhost:5050/")]
         [InlineData(ServerType.IISExpress, RuntimeFlavor.Clr, RuntimeArchitecture.x64, "http://localhost:5051/")]
         public async Task NtlmAuthentication(ServerType serverType, RuntimeFlavor runtimeFlavor, RuntimeArchitecture architecture, string applicationBaseUrl)