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 a9c5934ecd3..1060d32129a 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
@@ -572,7 +572,15 @@ protected override void ProcessRecord()
                                     // Disable writing to the OutFile.
                                     OutFile = null;
                                 }
-
+                                
+                                // Detect insecure redirection
+                                if (!AllowInsecureRedirect && response.RequestMessage.RequestUri.Scheme == "https" && response.Headers.Location?.Scheme == "http")
+                                {
+                                        ErrorRecord er = new(new InvalidOperationException(), "InsecureRedirection", ErrorCategory.InvalidOperation, request);
+                                        er.ErrorDetails = new ErrorDetails(WebCmdletStrings.InsecureRedirection);
+                                        ThrowTerminatingError(er);
+                                }
+                                
                                 if (ShouldCheckHttpStatus && !_isSuccess)
                                 {
                                     string message = string.Format(
diff --git a/src/Microsoft.PowerShell.Commands.Utility/resources/WebCmdletStrings.resx b/src/Microsoft.PowerShell.Commands.Utility/resources/WebCmdletStrings.resx
index bea0ae7d28a..a9628c647e3 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/resources/WebCmdletStrings.resx
+++ b/src/Microsoft.PowerShell.Commands.Utility/resources/WebCmdletStrings.resx
@@ -159,12 +159,15 @@
   <data name="DuplicateKeysInJsonString" xml:space="preserve">
     <value>Cannot convert the JSON string because a dictionary that was converted from the string contains the duplicated key '{0}'.</value>
   </data>
-  <data name="KeysWithDifferentCasingInJsonString" xml:space="preserve">
-    <value>Cannot convert the JSON string because it contains keys with different casing. Please use the -AsHashTable switch instead. The key that was attempted to be added to the existing key '{0}' was '{1}'.</value>
-  </data>
   <data name="IEDomNotSupported" xml:space="preserve">
     <value>The response content cannot be parsed because the Internet Explorer engine is not available, or Internet Explorer's first-launch configuration is not complete. Specify the UseBasicParsing parameter and try again. </value>
   </data>
+  <data name="InsecureRedirection" xml:space="preserve">
+    <value>Cannot follow an insecure redirection by default. Reissue the command specifying the -AllowInsecureRedirect switch. </value>
+  </data> 
+  <data name="KeysWithDifferentCasingInJsonString" xml:space="preserve">
+    <value>Cannot convert the JSON string because it contains keys with different casing. Please use the -AsHashTable switch instead. The key that was attempted to be added to the existing key '{0}' was '{1}'.</value>
+  </data>
   <data name="MaximumRedirectionCountExceeded" xml:space="preserve">
     <value>The maximum redirection count has been exceeded. To increase the number of redirections allowed, supply a higher value to the -MaximumRedirection parameter.</value>
   </data>
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 35262d8bf41..0c65e524034 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -1029,7 +1029,7 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
             $command = "Invoke-WebRequest -Uri '$uri' -SkipCertificateCheck"
 
             $result = ExecuteWebCommand -command $command
-            $result.Error.FullyQualifiedErrorId | Should -Be "WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeWebRequestCommand"
+            $result.Error.FullyQualifiedErrorId | Should -Be "InsecureRedirection,Microsoft.PowerShell.Commands.InvokeWebRequestCommand"
         }
     }
 
@@ -2732,7 +2732,7 @@ Describe "Invoke-RestMethod tests" -Tags "Feature", "RequireAdminOnWindows" {
         $command = "Invoke-RestMethod -Uri '$uri' -SkipCertificateCheck"
 
         $result = ExecuteWebCommand -command $command
-        $result.Error.FullyQualifiedErrorId | Should -Be "WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeRestMethodCommand"
+        $result.Error.FullyQualifiedErrorId | Should -Be "InsecureRedirection,Microsoft.PowerShell.Commands.InvokeRestMethodCommand"
     }
 
     #endregion Redirect tests