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 00828fec4b9..a79e40f492c 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
@@ -11,6 +11,7 @@
 using System.Collections;
 using System.Globalization;
 using System.Security;
+using System.Security.Authentication;
 using System.Security.Cryptography;
 using System.Security.Cryptography.X509Certificates;
 #if !CORECLR
@@ -46,6 +47,35 @@ public enum WebAuthenticationType
         OAuth,
     }
 
+    // WebSslProtocol is used because not all SslProtocols are supported by HttpClientHandler.
+    // Also SslProtocols.Default is not the "default" for HttpClientHandler as SslProtocols.Ssl3 is not supported.
+    /// <summary>
+    /// The valid values for the -SslProtocol parameter for Invoke-RestMethod and Invoke-WebRequest
+    /// </summary>
+    [Flags]
+    public enum WebSslProtocol
+    {
+        /// <summary>
+        ///  No SSL protocol will be set and the system defaults will be used.
+        /// </summary>
+        Default = 0,
+
+        /// <summary>
+        /// Specifies the TLS 1.0 security protocol. The TLS protocol is defined in IETF RFC 2246.
+        /// </summary>
+        Tls = SslProtocols.Tls,
+
+        /// <summary>
+        ///  Specifies the TLS 1.1 security protocol. The TLS protocol is defined in IETF RFC 4346.
+        /// </summary>
+        Tls11 = SslProtocols.Tls11,
+
+        /// <summary>
+        /// Specifies the TLS 1.2 security protocol. The TLS protocol is defined in IETF RFC 5246
+        /// </summary>
+        Tls12 = SslProtocols.Tls12
+    }
+
     /// <summary>
     /// Base class for Invoke-RestMethod and Invoke-WebRequest commands.
     /// </summary>
@@ -137,6 +167,12 @@ public abstract partial class WebRequestPSCmdlet : PSCmdlet
         [Parameter]
         public virtual SwitchParameter SkipCertificateCheck { get; set; }
 
+        /// <summary>
+        /// Gets or sets the TLS/SSL protocol used by the Web Cmdlet
+        /// </summary>
+        [Parameter]
+        public virtual WebSslProtocol SslProtocol { get; set; } = WebSslProtocol.Default;
+
         /// <summary>
         /// Gets or sets the Token property. Token is required by Authentication OAuth and Bearer.
         /// </summary>
diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebRequestPSCmdlet.CoreClr.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebRequestPSCmdlet.CoreClr.cs
index f5322ddc129..630f66804c6 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebRequestPSCmdlet.CoreClr.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebRequestPSCmdlet.CoreClr.cs
@@ -13,6 +13,7 @@
 using System.Text;
 using System.Collections;
 using System.Globalization;
+using System.Security.Authentication;
 using System.Security.Cryptography;
 using System.Threading;
 using System.Xml;
@@ -192,6 +193,9 @@ internal virtual HttpClient GetHttpClient(bool handleRedirect)
                 }
             }
 
+            handler.SslProtocols = (SslProtocols)SslProtocol;
+
+
             HttpClient httpClient = new HttpClient(handler);
 
             // check timeout setting (in seconds instead of milliseconds as in HttpWebRequest)
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 8dc1b1aaaef..fa5b15e8c24 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -1414,6 +1414,70 @@ Describe "Invoke-WebRequest tests" -Tags "Feature" {
         }
     }
 
+    Context "Invoke-WebRequest -SslProtocol Test" {
+        It "Verifies Invoke-WebRequest -SslProtocol <SslProtocol> works on <ActualProtocol>" -TestCases @(
+            @{SslProtocol = 'Default'; ActualProtocol = 'Default'}
+            @{SslProtocol = 'Tls'; ActualProtocol = 'Tls'}
+            @{SslProtocol = 'Tls11'; ActualProtocol = 'Tls11'}
+            @{SslProtocol = 'Tls12'; ActualProtocol = 'Tls12'}
+            # macOS does not support multiple SslProtocols
+            if (-not $IsMacOS) 
+            {
+                @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls12'}
+                @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls12'}
+                @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls11'}
+                @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls11'}
+                @{SslProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls11'}
+                @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls'}
+                @{SslProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls'}
+                @{SslProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls'}
+            }
+            # macOS does not support multiple SslProtocols and possible CoreFX for this combo on Linux
+            if($IsWindows)
+            {
+                
+                @{SslProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls12'}
+            }
+        ) {
+            param($SslProtocol, $ActualProtocol)
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https -SslProtocol $ActualProtocol
+                SslProtocol = $SslProtocol
+                SkipCertificateCheck = $true
+            }
+            $response = Invoke-WebRequest @params
+            $result = $Response.Content | ConvertFrom-Json
+
+            $result.headers.Host | Should Be $params.Uri.Authority
+        }
+
+        It "Verifies Invoke-WebRequest -SslProtocol -SslProtocol <IntendedProtocol> fails on a <ActualProtocol> only connection" -TestCases @(
+            @{IntendedProtocol = 'Tls';   ActualProtocol = 'Tls12'}
+            @{IntendedProtocol = 'Tls';   ActualProtocol = 'Tls11'}
+            @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls12'}
+            @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls'}
+            @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls'}
+            @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls11'}
+            # macOS does not support multiple SslProtocols
+            if (-not $IsMacOS) 
+            {
+                @{IntendedProtocol = 'Tls11, Tls12';   ActualProtocol = 'Tls'}
+                @{IntendedProtocol = 'Tls, Tls12';   ActualProtocol = 'Tls11'}
+                @{IntendedProtocol = 'Tls, Tls11';   ActualProtocol = 'Tls12'}
+            }
+        ) {
+            param( $IntendedProtocol, $ActualProtocol)
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https -SslProtocol $ActualProtocol
+                SslProtocol = $IntendedProtocol
+                SkipCertificateCheck = $true
+                ErrorAction = 'Stop'
+            }
+            { Invoke-WebRequest @params } | ShouldBeErrorId 'WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeWebRequestCommand'
+        }
+
+    }
+
     BeforeEach {
         if ($env:http_proxy) {
             $savedHttpProxy = $env:http_proxy
@@ -2332,6 +2396,69 @@ Describe "Invoke-RestMethod tests" -Tags "Feature" {
         }
     }
 
+    Context "Invoke-RestMethod -SslProtocol Test" {
+        It "Verifies Invoke-RestMethod -SslProtocol <SslProtocol> works on <ActualProtocol>" -TestCases @(
+            @{SslProtocol = 'Default'; ActualProtocol = 'Default'}
+            @{SslProtocol = 'Tls'; ActualProtocol = 'Tls'}
+            @{SslProtocol = 'Tls11'; ActualProtocol = 'Tls11'}
+            @{SslProtocol = 'Tls12'; ActualProtocol = 'Tls12'}
+            # macOS does not support multiple SslProtocols
+            if (-not $IsMacOS) 
+            {
+                @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls12'}
+                @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls12'}
+                @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls11'}
+                @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls11'}
+                @{SslProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls11'}
+                @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls'}
+                @{SslProtocol = 'Tls, Tls11'; ActualProtocol = 'Tls'}
+                @{SslProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls'}
+            }
+            # macOS does not support multiple SslProtocols and possible CoreFX for this combo on Linux
+            if($IsWindows)
+            {
+                @{SslProtocol = 'Tls, Tls12'; ActualProtocol = 'Tls12'}
+            }
+        ) {
+            param($SslProtocol, $ActualProtocol)
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https -SslProtocol $ActualProtocol
+                SslProtocol = $SslProtocol
+                SkipCertificateCheck = $true
+            }
+            $result = Invoke-RestMethod @params
+
+            $result.headers.Host | Should Be $params.Uri.Authority
+        }
+
+        It "Verifies Invoke-RestMethod -SslProtocol <IntendedProtocol> fails on a <ActualProtocol> only connection" -TestCases @(
+            @{IntendedProtocol = 'Tls';   ActualProtocol = 'Tls12'}
+            @{IntendedProtocol = 'Tls';   ActualProtocol = 'Tls11'}
+            @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls12'}
+            @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls'}
+            @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls'}
+            @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls11'}
+            # macOS does not support multiple SslProtocols
+            if (-not $IsMacOS) 
+            {
+                @{IntendedProtocol = 'Tls11, Tls12';   ActualProtocol = 'Tls'}
+                @{IntendedProtocol = 'Tls, Tls12';   ActualProtocol = 'Tls11'}
+                @{IntendedProtocol = 'Tls, Tls11';   ActualProtocol = 'Tls12'}
+            }
+        ) {
+            param( $IntendedProtocol, $ActualProtocol)
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https -SslProtocol $ActualProtocol
+                SslProtocol = $IntendedProtocol
+                SkipCertificateCheck = $true
+                ErrorAction = 'Stop'
+            }
+            { Invoke-RestMethod @params } | ShouldBeErrorId 'WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeRestMethodCommand'
+        }
+
+
+    }
+
     BeforeEach {
         if ($env:http_proxy) {
             $savedHttpProxy = $env:http_proxy
diff --git a/test/tools/Modules/WebListener/README.md b/test/tools/Modules/WebListener/README.md
index f66d94b2c16..0bb257d8f09 100644
--- a/test/tools/Modules/WebListener/README.md
+++ b/test/tools/Modules/WebListener/README.md
@@ -1,13 +1,13 @@
 # WebListener Module
 
-A PowerShell module for managing the WebListener App. The included SelF-Signed Certificate `ServerCert.pfx` has the password set to `password` and is issued for the Client and Server Authentication key usages. This certificate is used by the WebListener App for SSL/TLS. The included SelF-Signed Certificate `ClientCert.pfx` has the password set to `password` and has not been issued for any specific key usage. This Certificate is used for Client Certificate Authentication with the WebListener App.
+A PowerShell module for managing the WebListener App. The included SelF-Signed Certificate `ServerCert.pfx` has the password set to `password` and is issued for the Client and Server Authentication key usages. This certificate is used by the WebListener App for SSL/TLS. The included SelF-Signed Certificate `ClientCert.pfx` has the password set to `password` and has not been issued for any specific key usage. This Certificate is used for Client Certificate Authentication with the WebListener App. The port used for `-HttpsPort` will use TLS 1.2.
 
 # Running WebListener
 
 ```powershell
 Import-Module .\build.psm1
 Publish-PSTestTools
-$Listener = Start-WebListener -HttpPort 8083 -HttpsPort 8084
+$Listener = Start-WebListener -HttpPort 8083 -HttpsPort 8084 -Tls11Port 8085 -TlsPort 8086
 ```
 
 # Stopping WebListener
diff --git a/test/tools/Modules/WebListener/WebListener.psm1 b/test/tools/Modules/WebListener/WebListener.psm1
index a3125d07c6b..1e4ea444bf2 100644
--- a/test/tools/Modules/WebListener/WebListener.psm1
+++ b/test/tools/Modules/WebListener/WebListener.psm1
@@ -2,6 +2,8 @@ Class WebListener
 {
     [int]$HttpPort
     [int]$HttpsPort
+    [int]$Tls11Port
+    [int]$TlsPort
     [System.Management.Automation.Job]$Job
 
     WebListener () { }
@@ -36,7 +38,13 @@ function Start-WebListener
         [int]$HttpPort = 8083,
 
         [ValidateRange(1,65535)]
-        [int]$HttpsPort = 8084
+        [int]$HttpsPort = 8084,
+
+        [ValidateRange(1,65535)]
+        [int]$Tls11Port = 8085,
+
+        [ValidateRange(1,65535)]
+        [int]$TlsPort = 8086
     )
     
     process 
@@ -58,11 +66,13 @@ function Start-WebListener
         $Job = Start-Job {
             $path = Split-Path -parent (get-command WebListener).Path
             Push-Location $path
-            dotnet $using:appDll $using:serverPfxPath $using:serverPfxPassword $using:HttpPort $using:HttpsPort
+            dotnet $using:appDll $using:serverPfxPath $using:serverPfxPassword $using:HttpPort $using:HttpsPort $using:Tls11Port $using:TlsPort
         }
         $Script:WebListener = [WebListener]@{
             HttpPort  = $HttpPort 
             HttpsPort = $HttpsPort
+            Tls11Port = $Tls11Port
+            TlsPort   = $TlsPort
             Job       = $Job
         }
         # Wait until the app is running or until the initTimeoutSeconds have been reached
@@ -112,6 +122,10 @@ function Get-WebListenerUrl {
     [OutputType([Uri])]
     param (
         [switch]$Https,
+
+        [ValidateSet('Default', 'Tls12', 'Tls11', 'Tls')]
+        [string]$SslProtocol = 'Default',
+
         [ValidateSet(
             'Cert',
             'Compression',
@@ -140,9 +154,16 @@ function Get-WebListenerUrl {
         $Uri.Host = 'localhost'
         $Uri.Port = $runningListener.HttpPort
         $Uri.Scheme = 'Http'
+
         if ($Https.IsPresent)
         {
-            $Uri.Port = $runningListener.HttpsPort
+            switch ($SslProtocol)
+            {
+                'Tls11' { $Uri.Port = $runningListener.Tls11Port }
+                'Tls'   { $Uri.Port = $runningListener.TlsPort }
+                # The base HTTPs port is configured for Tls12 only
+                default { $Uri.Port = $runningListener.HttpsPort }
+            }
             $Uri.Scheme = 'Https'
         }
 
diff --git a/test/tools/WebListener/Program.cs b/test/tools/WebListener/Program.cs
index 124f28f7e8d..e0706c9a374 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() != 4)
+            if (args.Count() != 6)
             {
-                System.Console.WriteLine("Required: <CertificatePath> <CertificatePassword> <HTTPPortNumber> <HTTPSPortNumber>");  
+                System.Console.WriteLine("Required: <CertificatePath> <CertificatePassword> <HTTPPortNumber> <HTTPSPortNumberTls2> <HTTPSPortNumberTls11> <HTTPSPortNumberTls>");
                 Environment.Exit(1); 
             }
             BuildWebHost(args).Run();
@@ -44,6 +44,28 @@ public static IWebHost BuildWebHost(string[] args) =>
                        httpsOption.ServerCertificate = certificate;
                        listenOptions.UseHttps(httpsOption);
                    });
+                   options.Listen(IPAddress.Loopback, int.Parse(args[4]), listenOptions =>
+                   {
+                       var certificate = new X509Certificate2(args[0], args[1]);
+                       HttpsConnectionAdapterOptions httpsOption = new HttpsConnectionAdapterOptions();
+                       httpsOption.SslProtocols = SslProtocols.Tls11;
+                       httpsOption.ClientCertificateMode = ClientCertificateMode.AllowCertificate;
+                       httpsOption.ClientCertificateValidation = (inCertificate, inChain, inPolicy) => {return true;};
+                       httpsOption.CheckCertificateRevocation = false;
+                       httpsOption.ServerCertificate = certificate;
+                       listenOptions.UseHttps(httpsOption);
+                   });
+                   options.Listen(IPAddress.Loopback, int.Parse(args[5]), listenOptions =>
+                   {
+                       var certificate = new X509Certificate2(args[0], args[1]);
+                       HttpsConnectionAdapterOptions httpsOption = new HttpsConnectionAdapterOptions();
+                       httpsOption.SslProtocols = SslProtocols.Tls;
+                       httpsOption.ClientCertificateMode = ClientCertificateMode.AllowCertificate;
+                       httpsOption.ClientCertificateValidation = (inCertificate, inChain, inPolicy) => {return true;};
+                       httpsOption.CheckCertificateRevocation = false;
+                       httpsOption.ServerCertificate = certificate;
+                       listenOptions.UseHttps(httpsOption);
+                   });
                 })
                 .Build();
     }
diff --git a/test/tools/WebListener/README.md b/test/tools/WebListener/README.md
index 04dbd20ccb5..2a26200b826 100644
--- a/test/tools/WebListener/README.md
+++ b/test/tools/WebListener/README.md
@@ -8,24 +8,26 @@ ASP.NET Core 2.0 app for testing HTTP and HTTPS Requests.
 dotnet restore
 dotnet publish --output bin --configuration Release
 cd bin
-dotnet WebListener.dll ServerCert.pfx password 8083 8084
+dotnet WebListener.dll ServerCert.pfx password 8083 8084 8085 8086
 ```
 
-The test site can then be accessed via `http://localhost:8083/` or `https://localhost:8084/`.  
+The test site can then be accessed via `http://localhost:8083/`, `https://localhost:8084/`, `https://localhost:8085/`, or `https://localhost:8086/`.
 
-The `WebListener.dll` takes 4 arguments: 
+The `WebListener.dll` takes 6 arguments: 
 
 * The path to the Server Certificate
 * The Server Certificate Password
 * The TCP Port to bind on for HTTP
-* The TCP Port to bind on for HTTPS
+* The TCP Port to bind on for HTTPS using TLS 1.2
+* The TCP Port to bind on for HTTPS using TLS 1.1
+* The TCP Port to bind on for HTTPS using TLS 1.0
 
 # Run With WebListener Module
 
 ```powershell
 Import-Module .\build.psm1
 Publish-PSTestTools
-$Listener = Start-WebListener -HttpPort 8083 -HttpsPort 8084
+$Listener = Start-WebListener -HttpPort 8083 -HttpsPort 8084 -Tls11Port 8085 -TlsPort = 8086
 ```
 
 # Tests