diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
index 94dde3c00fb..7cba6e8ba23 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
@@ -78,7 +78,12 @@ public enum WebSslProtocol
         /// <summary>
         /// Specifies the TLS 1.2 security protocol. The TLS protocol is defined in IETF RFC 5246.
         /// </summary>
-        Tls12 = SslProtocols.Tls12
+        Tls12 = SslProtocols.Tls12,
+
+        /// <summary>
+        /// Specifies the TLS 1.3 security protocol. The TLS protocol is defined in IETF RFC 8446.
+        /// </summary>
+        Tls13 = SslProtocols.Tls13
     }
 
     /// <summary>
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index ba6185777f9..6cadb0c9f65 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -1688,18 +1688,25 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
 
     Context "Invoke-WebRequest -SslProtocol Test" {
         BeforeAll {
+            # We put Tls13 tests at pending due to modern OS limitations.
+            # Tracking issue https://github.com/PowerShell/PowerShell/issues/13439
+
             ## Test cases for the 1st 'It'
             $testCases1 = @(
                 @{ Test = @{SslProtocol = 'Default'; ActualProtocol = 'Default'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls'; ActualProtocol = 'Tls'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls11'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls12'; ActualProtocol = 'Tls12'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls13'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls12'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12, Tls13'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls12'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12, Tls13'; ActualProtocol = 'Tls11'}; Pending = $true }
                 @{ Test = @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls, Tls11, Tls13'; ActualProtocol = 'Tls'}; Pending = $true }
                 @{ Test = @{SslProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls'}; Pending = $false }
                 # Skipping intermediary protocols is not supported on all platforms
                 @{ Test = @{SslProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls'}; Pending = -not $IsWindows }
@@ -1707,13 +1714,19 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
             )
 
             $testCases2 = @(
+                @{ Test = @{IntendedProtocol = 'Tls'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{IntendedProtocol = 'Tls'; ActualProtocol = 'Tls12'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls'; ActualProtocol = 'Tls11'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls12'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls13'; ActualProtocol = 'Tls'}; Pending = $true }
                 @{ Test = @{IntendedProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls11, Tls12, Tls13'; ActualProtocol = 'Tls'}; Pending = $true }
+                @{ Test = @{IntendedProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls13'}; Pending = $true }
+                @{ Test = @{IntendedProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{IntendedProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls12'}; Pending = $false }
             )
@@ -3191,17 +3204,24 @@ Describe "Invoke-RestMethod tests" -Tags "Feature", "RequireAdminOnWindows" {
 
     Context "Invoke-RestMethod -SslProtocol Test" {
         BeforeAll {
+            # We put Tls13 tests at pending due to modern OS limitations.
+            # Tracking issue https://github.com/PowerShell/PowerShell/issues/13439
+
             $testCases1 = @(
                 @{ Test = @{SslProtocol = 'Default'; ActualProtocol = 'Default'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls'; ActualProtocol = 'Tls'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls11'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls12'; ActualProtocol = 'Tls12'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls13'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls12'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12, Tls13'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls12'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12, Tls13'; ActualProtocol = 'Tls11'}; Pending = $true }
                 @{ Test = @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls, Tls11, Tls13'; ActualProtocol = 'Tls'}; Pending = $true }
                 @{ Test = @{SslProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls'}; Pending = $false }
                 # Skipping intermediary protocols is not supported on all platforms
                 @{ Test = @{SslProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls'}; Pending = -not $IsWindows }
@@ -3209,13 +3229,19 @@ Describe "Invoke-RestMethod tests" -Tags "Feature", "RequireAdminOnWindows" {
             )
 
             $testCases2 = @(
+                @{ Test = @{IntendedProtocol = 'Tls'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{IntendedProtocol = 'Tls'; ActualProtocol = 'Tls12'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls'; ActualProtocol = 'Tls11'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls12'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls13'; ActualProtocol = 'Tls'}; Pending = $true }
                 @{ Test = @{IntendedProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls11, Tls12, Tls13'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls13'}; Pending = $true }
+                @{ Test = @{IntendedProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls13'}; Pending = $true }
                 @{ Test = @{IntendedProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls12'}; Pending = $false }
             )
diff --git a/test/tools/Modules/WebListener/WebListener.psm1 b/test/tools/Modules/WebListener/WebListener.psm1
index 6122a7a8a4b..6436da97d1c 100644
--- a/test/tools/Modules/WebListener/WebListener.psm1
+++ b/test/tools/Modules/WebListener/WebListener.psm1
@@ -108,7 +108,10 @@ function Start-WebListener
         [int]$Tls11Port = 8085,
 
         [ValidateRange(1,65535)]
-        [int]$TlsPort = 8086
+        [int]$TlsPort = 8086,
+
+        [ValidateRange(1,65535)]
+        [int]$Tls13Port = 8087
     )
 
     process
@@ -141,10 +144,11 @@ function Start-WebListener
             'serverPfxPassword: {0}' -f $using:serverPfxPassword
             'HttpPort: {0}' -f $using:HttpPort
             'Https: {0}' -f $using:HttpsPort
+            'Tls13Port: {0}' -f $using:Tls13Port
             'Tls11Port: {0}' -f $using:Tls11Port
             'TlsPort: {0}' -f $using:TlsPort
             $env:ASPNETCORE_ENVIRONMENT = 'Development'
-            & $using:appExe $using:serverPfxPath $using:serverPfxPassword $using:HttpPort $using:HttpsPort $using:Tls11Port $using:TlsPort
+            & $using:appExe $using:serverPfxPath $using:serverPfxPassword $using:HttpPort $using:HttpsPort $using:Tls11Port $using:TlsPort $using:Tls13Port
         }
 
         $Script:WebListener = [WebListener]@{
@@ -208,7 +212,7 @@ function Get-WebListenerUrl {
     param (
         [switch]$Https,
 
-        [ValidateSet('Default', 'Tls12', 'Tls11', 'Tls')]
+        [ValidateSet('Default', 'Tls13', 'Tls12', 'Tls11', 'Tls')]
         [string]$SslProtocol = 'Default',
 
         [ValidateSet(
diff --git a/test/tools/WebListener/Program.cs b/test/tools/WebListener/Program.cs
index 691ef60b7c2..237e01ab744 100644
--- a/test/tools/WebListener/Program.cs
+++ b/test/tools/WebListener/Program.cs
@@ -20,9 +20,9 @@ public class Program
     {
         public static void Main(string[] args)
         {
-            if (args.Count() != 6)
+            if (args.Count() != 7)
             {
-                System.Console.WriteLine("Required: <CertificatePath> <CertificatePassword> <HTTPPortNumber> <HTTPSPortNumberTls2> <HTTPSPortNumberTls11> <HTTPSPortNumberTls>");
+                System.Console.WriteLine("Required: <CertificatePath> <CertificatePassword> <HTTPPortNumber> <HTTPSPortNumberTls12> <HTTPSPortNumberTls11> <HTTPSPortNumberTls> <HTTPSPortNumberTls12>");
                 Environment.Exit(1);
             }
 
@@ -68,6 +68,17 @@ public static IWebHost BuildWebHost(string[] args) =>
                        httpsOption.ServerCertificate = certificate;
                        listenOptions.UseHttps(httpsOption);
                    });
+                   options.Listen(IPAddress.Loopback, int.Parse(args[6]), listenOptions =>
+                   {
+                       var certificate = new X509Certificate2(args[0], args[1]);
+                       HttpsConnectionAdapterOptions httpsOption = new HttpsConnectionAdapterOptions();
+                       httpsOption.SslProtocols = SslProtocols.Tls13;
+                       httpsOption.ClientCertificateMode = ClientCertificateMode.AllowCertificate;
+                       httpsOption.ClientCertificateValidation = (inCertificate, inChain, inPolicy) => {return true;};
+                       httpsOption.CheckCertificateRevocation = false;
+                       httpsOption.ServerCertificate = certificate;
+                       listenOptions.UseHttps(httpsOption);
+                   });
                 })
                 .Build();
     }