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 c078faaed5c..79ec2903665 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
@@ -592,12 +592,20 @@ protected override void ProcessRecord()
                                 OutFile = null;
                             }
 
-                            // Detect insecure redirection
-                            if (!AllowInsecureRedirect && response.RequestMessage.RequestUri.Scheme == "https" && response.Headers.Location?.Scheme == "http")
+                            // Detect insecure redirection.
+                            if (!AllowInsecureRedirect)
                             {
-                                ErrorRecord er = new(new InvalidOperationException(), "InsecureRedirection", ErrorCategory.InvalidOperation, request);
-                                er.ErrorDetails = new ErrorDetails(WebCmdletStrings.InsecureRedirection);
-                                ThrowTerminatingError(er);
+                                // We will skip detection if either of the URIs is relative, because the 'Scheme' property is not supported on a relative URI.
+                                // If we have to skip the check, an error may be thrown later if it's actually an insecure https-to-http redirect.
+                                bool originIsHttps = response.RequestMessage.RequestUri.IsAbsoluteUri && response.RequestMessage.RequestUri.Scheme == "https";
+                                bool destinationIsHttp = response.Headers.Location is not null && response.Headers.Location.IsAbsoluteUri && response.Headers.Location.Scheme == "http";
+
+                                if (originIsHttps && destinationIsHttp)
+                                {
+                                    ErrorRecord er = new(new InvalidOperationException(), "InsecureRedirection", ErrorCategory.InvalidOperation, request);
+                                    er.ErrorDetails = new ErrorDetails(WebCmdletStrings.InsecureRedirection);
+                                    ThrowTerminatingError(er);
+                                }
                             }
 
                             if (ShouldCheckHttpStatus && !_isSuccess)
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 5f1e6e4bae3..b07afbe3627 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -1149,6 +1149,15 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
             $result = ExecuteWebCommand -command $command
             $result.Error.FullyQualifiedErrorId | Should -Be "InsecureRedirection,Microsoft.PowerShell.Commands.InvokeWebRequestCommand"
         }
+
+        It "Validate Invoke-WebRequest Https to Http (No Scheme) redirect without -AllowInsecureRedirect" {
+            $httpUri = Get-WebListenerUrl -Test 'Get'
+            $uri = Get-WebListenerUrl -Test 'Redirect' -Https -Query @{destination = $httpUri.Authority}
+            $command = "Invoke-WebRequest -Uri '$uri' -SkipCertificateCheck"
+
+            $result = ExecuteWebCommand -command $command
+            $result.Error.FullyQualifiedErrorId | Should -Be "WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeWebRequestCommand"
+        }
     }
 
 
@@ -3100,6 +3109,15 @@ Describe "Invoke-RestMethod tests" -Tags "Feature", "RequireAdminOnWindows" {
         $result.Error.FullyQualifiedErrorId | Should -Be "InsecureRedirection,Microsoft.PowerShell.Commands.InvokeRestMethodCommand"
     }
 
+    It "Validate Invoke-RestMethod Https to Http (No Scheme) redirect without -AllowInsecureRedirect" {
+        $httpUri = Get-WebListenerUrl -Test 'Get'
+        $uri = Get-WebListenerUrl -Test 'Redirect' -Https -Query @{destination = $httpUri.Authority}
+        $command = "Invoke-RestMethod -Uri '$uri' -SkipCertificateCheck"
+
+        $result = ExecuteWebCommand -command $command
+        $result.Error.FullyQualifiedErrorId | Should -Be "WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeRestMethodCommand"
+    }
+
     #endregion Redirect tests
 
     Context "Invoke-RestMethod SkipHeaderVerification Tests" {