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 5e8055572a3..30792f3938b 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
@@ -164,6 +164,12 @@ public abstract partial class WebRequestPSCmdlet : PSCmdlet
         [Parameter]
         public virtual SwitchParameter SkipCertificateCheck { get; set; }
 
+        /// <summary>
+        /// gets or sets the CertificateValidationScript property. This will be ignored if SkipCertificateCheck is set.
+        /// </summary>
+        [Parameter]
+        public virtual ScriptBlock CertificateValidationScript { get; set; }
+
         /// <summary>
         /// Gets or sets the TLS/SSL protocol used by the Web Cmdlet
         /// </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 0163b5f0958..acfad4388d5 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
@@ -4,15 +4,18 @@
 
 using System;
 using System.Management.Automation;
+using System.Management.Automation.Runspaces;
 using System.Net;
 using System.Net.Http;
 using System.Net.Http.Headers;
+using System.Net.Security;
 using System.IO;
 using System.Text;
 using System.Collections;
 using System.Globalization;
 using System.Security.Authentication;
 using System.Security.Cryptography;
+using System.Security.Cryptography.X509Certificates;
 using System.Threading;
 using System.Xml;
 using System.Collections.Generic;
@@ -173,6 +176,45 @@ internal virtual HttpClient GetHttpClient(bool handleRedirect)
                 handler.ServerCertificateCustomValidationCallback = HttpClientHandler.DangerousAcceptAnyServerCertificateValidator;
                 handler.ClientCertificateOptions = ClientCertificateOption.Manual;
             }
+            else if (CertificateValidationScript != null)
+            {
+                // validationCallBackWrapper wraps the CertificateValidationScript ScriptBlock so the async callback properly execute ScriptBlock
+                Func<HttpRequestMessage,X509Certificate2,X509Chain,SslPolicyErrors,bool> validationCallBackWrapper = 
+                    delegate(HttpRequestMessage httpRequestMessage, X509Certificate2 x509Certificate2, X509Chain x509Chain, SslPolicyErrors sslPolicyErrors)
+                    {
+                        InitialSessionState iss = InitialSessionState.CreateDefault();
+                        
+                        // Add $_ variable with the Delegate parameters as members
+                        PSObject dollarUnderbar = new PSObject();
+                        dollarUnderbar.Members.Add(new PSNoteProperty("Request", httpRequestMessage));
+                        dollarUnderbar.Members.Add(new PSNoteProperty("Certificate", x509Certificate2));
+                        dollarUnderbar.Members.Add(new PSNoteProperty("CertificateChain", x509Chain));
+                        dollarUnderbar.Members.Add(new PSNoteProperty("SslErrors", sslPolicyErrors));
+                        iss.Variables.Add(new SessionStateVariableEntry(name: "_", value: dollarUnderbar, description: String.Empty));
+
+                        Boolean result = false;
+                        try
+                        {
+                            using (Runspace rs = RunspaceFactory.CreateRunspace(iss))
+                            using (var ps = System.Management.Automation.PowerShell.Create())
+                            {
+                                ps.Runspace = rs;
+                                rs.Open();
+                                ps.AddScript(CertificateValidationScript.ToString());
+
+                                result = LanguagePrimitives.IsTrue(ps.Invoke().First());
+                            }
+                        }
+                        catch // Treat all exceptions as Certificate failures.
+                        {
+                            result = false;
+                        }
+
+                        return result;
+                    };
+
+                handler.ServerCertificateCustomValidationCallback = validationCallBackWrapper;
+            }
 
             // This indicates GetResponse will handle redirects.
             if (handleRedirect)
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index dc3bdce61ed..5e5b5ba8669 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -1557,6 +1557,58 @@ Describe "Invoke-WebRequest tests" -Tags "Feature" {
 
     }
 
+    Context "Invoke-WebRequest CertificateValidationScript Tests" {
+        It "Verifies Invoke-WebRequest -CertificateValidationScript can accept all certificates" -Pending:$PendingCertificateTest {
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https
+                ErrorAction = 'Stop'
+                CertificateValidationScript = { $true }
+            }
+            # WebListener uses a self-signed cert. Without -SkipCertificateCheck this would normally fail
+            $result = Invoke-WebRequest @Params
+            $jsonResult = $result.Content | ConvertFrom-Json
+            $jsonResult.Headers.Host | Should BeExactly $params.Uri.Authority
+        }
+
+        It "Verifies Invoke-WebRequest -CertificateValidationScript is ignored when -SkipCertificateCheck is present" {
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https
+                ErrorAction = 'Stop'
+                SkipCertificateCheck = $true
+                # This script would fail all certificates
+                CertificateValidationScript = { $false }                
+            }
+            $result = Invoke-WebRequest @Params
+            $jsonResult = $result.Content | ConvertFrom-Json
+            $jsonResult.Headers.Host | Should BeExactly $params.Uri.Authority
+        }
+
+        It 'Verifies Invoke-WebRequest -CertificateValidationScript script has a $_' -Pending:$PendingCertificateTest {
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https
+                ErrorAction = 'Stop'
+                CertificateValidationScript = { 
+                    $_.Certificate.Thumbprint -eq 'C8747A1C4A46E52EEC688A6766967010F86C58E3' -and
+                    $_.CertificateChain.ChainElements[0].Certificate.Thumbprint -eq 'C8747A1C4A46E52EEC688A6766967010F86C58E3' -and
+                    $_.SslErrors -eq 'RemoteCertificateChainErrors' -and
+                    $_.Request.Method.Method -eq 'GET'
+                }
+            }
+            $result = Invoke-WebRequest @Params
+            $jsonResult = $result.Content | ConvertFrom-Json
+            $jsonResult.Headers.Host | Should BeExactly $params.Uri.Authority
+        }
+
+        It "Verifies Invoke-WebRequest -CertificateValidationScript treats exceptions as Certificate failures" -Pending:$PendingCertificateTest {
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https
+                ErrorAction = 'Stop'
+                CertificateValidationScript = { throw 'Bad Cert' }
+            }
+            { Invoke-WebRequest @Params } | ShouldBeErrorId 'WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeWebRequestCommand'
+        }
+    }
+
     BeforeEach {
         if ($env:http_proxy) {
             $savedHttpProxy = $env:http_proxy
@@ -2629,6 +2681,56 @@ Describe "Invoke-RestMethod tests" -Tags "Feature" {
         }
     }
 
+    Context "Invoke-RestMethod CertificateValidationScript Tests" {
+        It "Verifies Invoke-RestMethod -CertificateValidationScript can accept all certificates" -Pending:$PendingCertificateTest {
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https
+                ErrorAction = 'Stop'
+                CertificateValidationScript = { $true }
+            }
+            # WebListener uses a self-signed cert. Without -SkipCertificateCheck this would normally fail
+            $result = Invoke-RestMethod @Params
+            $result.Headers.Host | Should BeExactly $params.Uri.Authority
+        }
+
+        It "Verifies Invoke-RestMethod -CertificateValidationScript is ignored when -SkipCertificateCheck is present" {
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https
+                ErrorAction = 'Stop'
+                SkipCertificateCheck = $true
+                # This script would fail all certificates
+                CertificateValidationScript = { $false }                
+            }
+            $result = Invoke-RestMethod @Params
+            $result.Headers.Host | Should BeExactly $params.Uri.Authority
+        }
+        
+        It 'Verifies Invoke-RestMethod -CertificateValidationScript script has a $_' -Pending:$PendingCertificateTest {
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https
+                ErrorAction = 'Stop'
+                CertificateValidationScript = {
+                    $WebListenerThumbprint = 'C8747A1C4A46E52EEC688A6766967010F86C58E3'
+                    $_.Certificate.Thumbprint -eq $WebListenerThumbprint -and
+                    $_.CertificateChain.ChainElements[0].Certificate.Thumbprint -eq $WebListenerThumbprint -and
+                    $_.SslErrors -eq 'RemoteCertificateChainErrors' -and
+                    $_.Request.Method.Method -eq 'GET'
+                }
+            }
+            $result = Invoke-RestMethod @Params 
+            $result.Headers.Host | Should BeExactly $params.Uri.Authority
+        }
+
+        It "Verifies Invoke-RestMethod -CertificateValidationScript treats exceptions as Certificate failures" -Pending:$PendingCertificateTest {
+            $params = @{
+                Uri = Get-WebListenerUrl -Test 'Get' -Https
+                ErrorAction = 'Stop'
+                CertificateValidationScript = { throw 'Bad Cert' }
+            }
+            { Invoke-RestMethod @Params } | ShouldBeErrorId 'WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeRestMethodCommand'
+        }
+    }
+
     BeforeEach {
         if ($env:http_proxy) {
             $savedHttpProxy = $env:http_proxy