diff --git a/src/Hosting/Server.IntegrationTesting/src/TestMatrix.cs b/src/Hosting/Server.IntegrationTesting/src/TestMatrix.cs
index deb7c17343..99ef336dc6 100644
--- a/src/Hosting/Server.IntegrationTesting/src/TestMatrix.cs
+++ b/src/Hosting/Server.IntegrationTesting/src/TestMatrix.cs
@@ -289,6 +289,15 @@ namespace Microsoft.AspNetCore.Server.IntegrationTesting
                     }
                 }
 
+                // https://github.com/aspnet/AspNetCore/issues/8329
+                if (hostingModel == HostingModel.OutOfProcess &&
+                    server == ServerType.IISExpress &&
+                    Environment.OSVersion.Version.Major == 6 &&
+                    Environment.OSVersion.Version.Minor == 1)
+                {
+                    continue;
+                }
+
                 variants.Add(new TestVariant()
                 {
                     Server = server,
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/AspNetCorePortTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/AspNetCorePortTests.cs
index e49d213b6b..66482eec43 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/AspNetCorePortTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/AspNetCorePortTests.cs
@@ -40,7 +40,7 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
                from s in new string[] { (_minPort - 1).ToString(), (_maxPort + 1).ToString(), "noninteger" }
                select new object[] { v, s };
 
-        [ConditionalTheory]
+        [ConditionalTheory(Skip = "https://github.com/aspnet/AspNetCore/issues/8329")]
         [MemberData(nameof(TestVariants))]
         public async Task EnvVarInWebConfig_Valid(TestVariant variant)
         {
@@ -56,7 +56,7 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
             Assert.Equal(port, new Uri(responseText).Port);
         }
 
-        [ConditionalTheory]
+        [ConditionalTheory(Skip = "https://github.com/aspnet/AspNetCore/issues/8329")]
         [MemberData(nameof(TestVariants))]
         public async Task EnvVarInWebConfig_Empty(TestVariant variant)
         {
@@ -72,7 +72,7 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
             Assert.InRange(new Uri(responseText).Port, _minPort, _maxPort);
         }
 
-        [ConditionalTheory]
+        [ConditionalTheory(Skip = "https://github.com/aspnet/AspNetCore/issues/8329")]
         [MemberData(nameof(InvalidTestVariants))]
         public async Task EnvVarInWebConfig_Invalid(TestVariant variant, string port)
         {
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/HelloWorldTest.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/HelloWorldTest.cs
index 965794248b..8166e52acd 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/HelloWorldTest.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/HelloWorldTest.cs
@@ -29,7 +29,7 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
                 .WithTfms(Tfm.NetCoreApp30)
                 .WithAllApplicationTypes();
 
-        [ConditionalTheory]
+        [ConditionalTheory(Skip = "https://github.com/aspnet/AspNetCore/issues/8329")]
         [MemberData(nameof(TestVariants))]
         public async Task HelloWorld(TestVariant variant)
         {
diff --git a/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/OutOfProcess/NtlmAuthentationTest.cs b/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/OutOfProcess/NtlmAuthentationTest.cs
index 1d1d549def..5a9df13799 100644
--- a/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/OutOfProcess/NtlmAuthentationTest.cs
+++ b/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/OutOfProcess/NtlmAuthentationTest.cs
@@ -32,7 +32,7 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
             => TestMatrix.ForServers(DeployerSelector.ServerType)
                 .WithTfms(Tfm.NetCoreApp30);
 
-        [ConditionalTheory]
+        [ConditionalTheory(Skip = "https://github.com/aspnet/AspNetCore/issues/8329")]
         [RequiresIIS(IISCapability.WindowsAuthentication)]
         [MemberData(nameof(TestVariants))]
         public async Task NtlmAuthentication(TestVariant variant)
diff --git a/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/RequiresIISAttribute.cs b/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/RequiresIISAttribute.cs
index 2e0a68b9f7..5bc43fc763 100644
--- a/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/RequiresIISAttribute.cs
+++ b/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/RequiresIISAttribute.cs
@@ -10,13 +10,22 @@ namespace Microsoft.AspNetCore.Server.IISIntegration.FunctionalTests
     [AttributeUsage(AttributeTargets.Assembly | AttributeTargets.Class | AttributeTargets.Method)]
     public sealed class RequiresIISAttribute : Attribute, ITestCondition
     {
-        public bool IsMet => IISExpressAncmSchema.SupportsInProcessHosting;
+        public bool IsMet { get ; } = IISExpressAncmSchema.SupportsInProcessHosting;
 
-        public string SkipReason => IISExpressAncmSchema.SkipReason;
+        public string SkipReason { get; } = IISExpressAncmSchema.SkipReason;
 
-        public RequiresIISAttribute() { }
+        public RequiresIISAttribute()
+        {
+            // https://github.com/aspnet/AspNetCore/issues/8329
+            if (Environment.OSVersion.Version.Major == 6 &&
+                Environment.OSVersion.Version.Minor == 1)
+            {
+                IsMet = false;
+                SkipReason = "Skipped on Windows 7";
+            }
+        }
 
-        public RequiresIISAttribute(IISCapability capabilities)
+        public RequiresIISAttribute(IISCapability capabilities) : this()
         {
             // IISCapabilities aren't pertinent to IISExpress
         }