diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/ClientDisconnectStress.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/ClientDisconnectStress.cs
index b72dda791e..605c1055ac 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/ClientDisconnectStress.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/ClientDisconnectStress.cs
@@ -22,6 +22,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData(HostingModel.InProcess)]
         [InlineData(HostingModel.OutOfProcess)]
         public async Task ClientDisconnectStress(HostingModel hostingModel)
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/HttpsTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/HttpsTests.cs
index b7491f805f..e4973e3de5 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/HttpsTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/HttpsTests.cs
@@ -73,6 +73,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         [ConditionalFact]
         [RequiresNewHandler]
         [RequiresNewShim]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Unexplained casing behavior change https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task ServerAddressesIncludesBaseAddress()
         {
             var appName = "\u041C\u043E\u0451\u041F\u0440\u0438\u043B\u043E\u0436\u0435\u043D\u0438\u0435";
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ErrorPagesTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ErrorPagesTests.cs
index 5104520781..1efcdb5479 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ErrorPagesTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ErrorPagesTests.cs
@@ -20,6 +20,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         public async Task IncludesAdditionalErrorPageTextInProcessHandlerLoadFailure_CorrectString()
         {
@@ -56,6 +57,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         public async Task IncludesAdditionalErrorPageTextOutOfProcessHandlerLoadFailure_CorrectString()
         {
@@ -78,6 +80,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         [RequiresNewHandler]
         public async Task IncludesAdditionalErrorPageTextInProcessStartupFailure_CorrectString()
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/EventLogTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/EventLogTests.cs
index 4ce5cef67b..1da3d1e4dc 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/EventLogTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/EventLogTests.cs
@@ -16,6 +16,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task CheckStartupEventLogMessage()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters();
@@ -28,6 +29,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task CheckShutdownEventLogMessage()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters();
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/FrebTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/FrebTests.cs
index 7573fc021d..6aaa57c6c7 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/FrebTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/FrebTests.cs
@@ -36,6 +36,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.FailedRequestTracingModule)]
         public async Task CheckCommonFrebEvents()
         {
@@ -49,6 +50,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresNewShim]
         [RequiresIIS(IISCapability.FailedRequestTracingModule)]
         public async Task FrebIncludesHResultFailures()
@@ -65,6 +67,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.FailedRequestTracingModule)]
         public async Task CheckFailedRequestEvents()
         {
@@ -80,6 +83,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         // I think this test is flaky due to freb file not being created quickly enough.
         // Adding extra logging, marking as flaky, and repeating should help
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [QuarantinedTest("https://github.com/dotnet/aspnetcore-internal/issues/2570")]
         [Repeat(10)]
         [RequiresIIS(IISCapability.FailedRequestTracingModule)]
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/LogPipeTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/LogPipeTests.cs
index 0b5b5a7333..93286432c9 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/LogPipeTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/LogPipeTests.cs
@@ -19,6 +19,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("ConsoleErrorWrite")]
         [InlineData("ConsoleWrite")]
         public async Task CheckStdoutLoggingToPipe_DoesNotCrashProcess(string path)
@@ -37,6 +38,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("ConsoleErrorWriteStartServer")]
         [InlineData("ConsoleWriteStartServer")]
         public async Task CheckStdoutLoggingToPipeWithFirstWrite(string path)
@@ -61,6 +63,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task CheckUnicodePipe()
         {
             var path = "CheckConsoleFunctions";
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/MaxRequestBodySizeTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/MaxRequestBodySizeTests.cs
index e4d951c63f..3883c82147 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/MaxRequestBodySizeTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/MaxRequestBodySizeTests.cs
@@ -115,6 +115,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresNewHandler]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         public async Task SetIISLimitMaxRequestBodyLogsWarning()
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ResetTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ResetTests.cs
index 89ec32af43..840d526ebc 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ResetTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ResetTests.cs
@@ -24,7 +24,8 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
     [Collection(PublishedSitesCollection.Name)]
     public class ResetTests : IISFunctionalTestBase
     {
-        private const string WindowsVersionForTrailers = "10.0.20180";
+        // TODO: This is just a guess, there is no build available yet with this feature.
+        private const string WindowsVersionForTrailers = "10.0.20300";
 
         public ResetTests(PublishedSitesFixture fixture) : base(fixture)
         {
@@ -45,7 +46,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         };
 
         public static readonly IEnumerable<KeyValuePair<string, string>> PostRequestHeaders = new[]
-{
+        {
             new KeyValuePair<string, string>(HeaderNames.Method, "POST"),
             new KeyValuePair<string, string>(HeaderNames.Scheme, "https"),
             new KeyValuePair<string, string>(HeaderNames.Authority, "localhost:80"),
@@ -355,7 +356,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalFact]
-        [MinimumOSVersion(OperatingSystems.Windows, "10.0.19529", SkipReason = "Reset support was added in Win10_20H2.")]
+        [MinimumOSVersion(OperatingSystems.Windows, WindowsVersionForTrailers, SkipReason = "Reset support was added in Win10_20H2.")]
         public async Task Reset_AfterCompleteAsync_NoReset()
         {
             var deploymentParameters = GetHttpsDeploymentParameters();
@@ -387,7 +388,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalFact]
-        [MinimumOSVersion(OperatingSystems.Windows, "10.0.19529", SkipReason = "Reset support was added in Win10_20H2.")]
+        [MinimumOSVersion(OperatingSystems.Windows, WindowsVersionForTrailers, SkipReason = "Reset support was added in Win10_20H2.")]
         public async Task Reset_CompleteAsyncDuringRequestBody_Resets()
         {
             var deploymentParameters = GetHttpsDeploymentParameters();
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ResponseTrailersTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ResponseTrailersTests.cs
index 8dd82d85aa..b419a66ea0 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ResponseTrailersTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ResponseTrailersTests.cs
@@ -18,7 +18,8 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
     [Collection(PublishedSitesCollection.Name)]
     public class ResponseTrailersTests : IISFunctionalTestBase
     {
-        private const string WindowsVersionForTrailers = "10.0.20180";
+        // TODO: We're just guessing for now, there isn't a stable build with all the features yet.
+        private const string WindowsVersionForTrailers = "10.0.20300";
 
         public ResponseTrailersTests(PublishedSitesFixture fixture) : base(fixture)
         {
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ShutdownTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ShutdownTests.cs
index 89deedee17..2296665f04 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ShutdownTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/ShutdownTests.cs
@@ -19,6 +19,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task ShutdownTimeoutIsApplied()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupExceptionTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupExceptionTests.cs
index 4dcd67f63c..e9cee3e958 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupExceptionTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupExceptionTests.cs
@@ -18,6 +18,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("CheckLargeStdErrWrites")]
         [InlineData("CheckLargeStdOutWrites")]
         [InlineData("CheckOversizedStdErrWrites")]
@@ -35,6 +36,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("CheckLargeStdErrWrites")]
         [InlineData("CheckLargeStdOutWrites")]
         [InlineData("CheckOversizedStdErrWrites")]
@@ -57,6 +59,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task CheckValidConsoleFunctions()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupTests.cs
index 71ac04c80c..220489dba6 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/Inprocess/StartupTests.cs
@@ -42,6 +42,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("bogus", "", @"Executable was not found at '.*?\\bogus.exe")]
         [InlineData("c:\\random files\\dotnet.exe", "something.dll", @"Could not find dotnet.exe at '.*?\\dotnet.exe'")]
         [InlineData(".\\dotnet.exe", "something.dll", @"Could not find dotnet.exe at '.*?\\.\\dotnet.exe'")]
@@ -95,6 +96,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("dotnet")]
         [InlineData("dotnet.EXE")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
@@ -151,6 +153,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [SkipIfNotAdmin]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         public async Task DoesNotStartIfDisabled()
         {
@@ -212,6 +215,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task DetectsOverriddenServer()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
@@ -229,6 +233,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task LogsStartupExceptionExitError()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
@@ -247,6 +252,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task LogsUnexpectedThreadExitError()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
@@ -264,6 +270,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task RemoveHostfxrFromApp_InProcessHostfxrAPIAbsent()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
@@ -329,6 +336,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresNewShim]
         public async Task RemoveHostfxrFromApp_InProcessHostfxrLoadFailure()
         {
@@ -352,6 +360,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task TargedDifferenceSharedFramework_FailedToFindNativeDependencies()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
@@ -371,6 +380,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task SingleExecutable_FailedToFindNativeDependencies()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
@@ -412,6 +422,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task RemoveInProcessReference_FailedToFindRequestHandler()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(Fixture.InProcessTestSite);
@@ -474,6 +485,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task CheckInvalidHostingModelParameter()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters();
@@ -496,6 +508,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         public static IEnumerable<object[]> InvalidConfigTransformationsScenarios => InvalidConfigTransformations.ToTheoryData();
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [MemberData(nameof(InvalidConfigTransformationsScenarios))]
         public async Task ReportsWebConfigAuthoringErrors(string scenario)
         {
@@ -701,6 +714,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         [RequiresNewHandler]
         [InlineData("ASPNETCORE_ENVIRONMENT", "Development")]
@@ -730,6 +744,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresNewHandler]
         public async Task ExceptionIsLoggedToEventLogAndPutInResponseWhenDeveloperExceptionPageIsEnabledViaWebConfig()
         {
@@ -754,6 +769,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         [RequiresNewHandler]
         [InlineData("ThrowInStartup")]
@@ -778,6 +794,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         [RequiresNewHandler]
         public async Task ExceptionIsNotLoggedToResponseWhenStartupHookIsDisabled()
@@ -801,6 +818,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresNewHandler]
         public async Task ExceptionIsLoggedToEventLogDoesNotWriteToResponse()
         {
@@ -824,6 +842,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
 
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresNewHandler]
         public async Task CanAddCustomStartupHook()
         {
@@ -841,6 +860,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.InProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresNewHandler]
         public async Task CanAddCustomStartupHookWhenIISOneIsDisabled()
         {
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/LogFileTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/LogFileTests.cs
index a18346f099..b8bd9b0aeb 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/LogFileTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/LogFileTests.cs
@@ -26,6 +26,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
                 .WithAllHostingModels();
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [MemberData(nameof(TestVariants))]
         public async Task CheckStdoutLoggingToFile(TestVariant variant)
         {
@@ -33,6 +34,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [MemberData(nameof(TestVariants))]
         public async Task CheckStdoutErrLoggingToFile(TestVariant variant)
         {
@@ -59,6 +61,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
 
         // Move to separate file
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [MemberData(nameof(TestVariants))]
         public async Task InvalidFilePathForLogs_ServerStillRuns(TestVariant variant)
         {
@@ -128,6 +131,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         [MemberData(nameof(TestVariants))]
         public async Task StartupMessagesLogFileSwitchedWhenLogFilePresentInWebConfig(TestVariant variant)
@@ -160,6 +164,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [MemberData(nameof(TestVariants))]
 
         public async Task DebugLogsAreWrittenToEventLog(TestVariant variant)
@@ -172,6 +177,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [MemberData(nameof(TestVariants))]
         [QuarantinedTest("https://github.com/dotnet/aspnetcore-internal/issues/2200")]
         public async Task CheckUTF8File(TestVariant variant)
@@ -206,6 +212,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [MemberData(nameof(TestVariants))]
         public async Task OnlyOneFileCreatedWithProcessStartTime(TestVariant variant)
         {
@@ -222,6 +229,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task CaptureLogsForOutOfProcessWhenProcessFailsToStart()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(HostingModel.OutOfProcess);
@@ -236,6 +244,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresNewShim]
         public async Task DisableRedirectionNoLogs()
         {
@@ -252,6 +261,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task CaptureLogsForOutOfProcessWhenProcessFailsToStart30KbMax()
         {
             var deploymentParameters = Fixture.GetBaseDeploymentParameters(HostingModel.OutOfProcess);
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/MultiApplicationTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/MultiApplicationTests.cs
index 15a9354108..054d192166 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/MultiApplicationTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/MultiApplicationTests.cs
@@ -36,6 +36,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task FailsAndLogsWhenRunningTwoInProcessApps()
         {
             var parameters = Fixture.GetBaseDeploymentParameters(HostingModel.InProcess);
@@ -57,6 +58,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData(HostingModel.OutOfProcess)]
         [InlineData(HostingModel.InProcess)]
         public async Task FailsAndLogsEventLogForMixedHostingModel(HostingModel firstApp)
diff --git a/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/GlobalVersionTests.cs b/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/GlobalVersionTests.cs
index e94c4503fb..e0ef07f6d5 100644
--- a/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/GlobalVersionTests.cs
+++ b/src/Servers/IIS/IIS/test/Common.FunctionalTests/OutOfProcess/GlobalVersionTests.cs
@@ -41,6 +41,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.OutOfProcess
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [RequiresIIS(IISCapability.PoolEnvironmentVariables)]
         [RequiresNewShim]
         public async Task GlobalVersion_EnvironmentVariableWorks()
@@ -87,6 +88,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.OutOfProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("2.1.0")]
         [InlineData("2.1.0-preview")]
         public async Task GlobalVersion_NewVersionNumber(string version)
@@ -108,6 +110,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.OutOfProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("2.1.0")]
         [InlineData("2.1.0-preview")]
         public async Task GlobalVersion_MultipleRequestHandlers_PicksHighestOne(string version)
@@ -131,6 +134,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests.OutOfProcess
         }
 
         [ConditionalTheory]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         [InlineData("2.1.0")]
         [InlineData("2.1.0-preview")]
         public async Task GlobalVersion_MultipleRequestHandlers_UpgradeWorks(string version)
diff --git a/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/InProcess/IISExpressShutdownTests.cs b/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/InProcess/IISExpressShutdownTests.cs
index b39eabff4f..31775aa19e 100644
--- a/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/InProcess/IISExpressShutdownTests.cs
+++ b/src/Servers/IIS/IIS/test/IISExpress.FunctionalTests/InProcess/IISExpressShutdownTests.cs
@@ -65,12 +65,14 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
         }
 
         [ConditionalFact]
+        [MaximumOSVersion(OperatingSystems.Windows, WindowsVersions.Win10_20H1, SkipReason = "Shutdown hangs https://github.com/dotnet/aspnetcore/issues/25107")]
         public async Task GracefulShutdown_DoesNotCrashProcess()
         {
             var parameters = Fixture.GetBaseDeploymentParameters();
             var result = await DeployAsync(parameters);
 
             var response = await result.HttpClient.GetAsync("/HelloWorld");
+            response.EnsureSuccessStatusCode();
             StopServer(gracefulShutdown: true);
             Assert.True(result.HostProcess.ExitCode == 0);
         }
@@ -82,6 +84,7 @@ namespace Microsoft.AspNetCore.Server.IIS.FunctionalTests
             var result = await DeployAsync(parameters);
 
             var response = await result.HttpClient.GetAsync("/HelloWorld");
+            response.EnsureSuccessStatusCode();
             StopServer(gracefulShutdown: false);
             Assert.True(result.HostProcess.ExitCode == 1);
         }