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 70f03f5ddef..c0b237fb256 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
@@ -107,6 +107,11 @@ public abstract class WebRequestPSCmdlet : PSCmdlet
         /// </summary>
         internal int _maximumFollowRelLink = int.MaxValue;
 
+        /// <summary>
+        /// Maximum number of Redirects to follow.
+        /// </summary>
+        internal int _maximumRedirection;
+
         /// <summary>
         /// Parse Rel Links.
         /// </summary>
@@ -549,6 +554,8 @@ protected override void ProcessRecord()
 
                             WriteVerbose(reqVerboseMsg);
 
+                            _maximumRedirection = WebSession.MaximumRedirection;
+
                             using HttpResponseMessage response = GetResponse(client, request, handleRedirect);
 
                             string contentType = ContentHelper.GetContentType(response);
@@ -1230,7 +1237,7 @@ internal virtual HttpResponseMessage GetResponse(HttpClient client, HttpRequestM
                 response = client.SendAsync(currentRequest, HttpCompletionOption.ResponseHeadersRead, _cancelToken.Token).GetAwaiter().GetResult();
 
                 if (handleRedirect
-                    && WebSession.MaximumRedirection is not 0
+                    && _maximumRedirection is not 0
                     && IsRedirectCode(response.StatusCode)
                     && response.Headers.Location is not null)
                 {
@@ -1238,9 +1245,9 @@ internal virtual HttpResponseMessage GetResponse(HttpClient client, HttpRequestM
                     _cancelToken = null;
 
                     // If explicit count was provided, reduce it for this redirection.
-                    if (WebSession.MaximumRedirection > 0)
+                    if (_maximumRedirection > 0)
                     {
-                        WebSession.MaximumRedirection--;
+                        _maximumRedirection--;
                     }
 
                     // For selected redirects, GET must be used with the redirected Location.
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 2da345fcd3a..d78f57141c6 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -617,7 +617,7 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
         param($proxy_address, $name, $protocol)
 
         # use external url, but with proxy the external url should not actually be called
-        $command = "Invoke-WebRequest -Uri ${protocol}://httpbin.org -Proxy '${protocol}://${proxy_address}' -SkipCertificateCheck"
+        $command = "Invoke-WebRequest -Uri ${protocol}://httpbin.org -Proxy '${protocol}://${proxy_address}'"
         $result = ExecuteWebCommand -command $command
         $command = "Invoke-WebRequest -Uri '${protocol}://${proxy_address}' -NoProxy"
         $expectedResult = ExecuteWebCommand -command $command
@@ -969,6 +969,42 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
             $response.Content.Headers."Authorization" | Should -BeExactly "test"
         }
 
+        It "Validates Invoke-WebRequest with -WebSession and -PreserveAuthorizationOnRedirect doesn't change session variable on multiple redirects: <redirectType>" -TestCases $redirectTests {
+            param($redirectType)
+
+            #[SuppressMessage("Microsoft.Security", "CS002:SecretInNextLine", Justification="Demo/doc/test secret.")]
+            $token = "testpassword" | ConvertTo-SecureString -AsPlainText -Force
+            $credential = [pscredential]::new("testuser", $token)
+            $certificate = Get-WebListenerClientCertificate
+            $headers = @{"Authorization" = "test"}
+            $proxy = (Get-WebListenerUrl).Authority
+            $uri = Get-WebListenerUrl -Test 'Redirect' -TestValue 2 -Query @{type = $redirectType}
+
+            $session = [Microsoft.PowerShell.Commands.WebRequestSession]::new()
+            $session.MaximumRedirection = 2
+            $session.MaximumRetryCount = 2
+            $session.RetryIntervalInSeconds = 2
+            $session.UseDefaultCredentials = $true
+            $null = Invoke-WebRequest -Uri $uri -PreserveAuthorizationOnRedirect -WebSession $session -AllowUnencryptedAuthentication -Headers $headers
+            $session.MaximumRedirection | Should -BeExactly 2
+            $session.MaximumRetryCount | Should -BeExactly 2
+            $session.RetryIntervalInSeconds | Should -BeExactly 2
+            $session.UseDefaultCredentials | Should -BeExactly $true
+
+            $session = [Microsoft.PowerShell.Commands.WebRequestSession]::new()
+            $session.Credentials = $credential
+            $session.Certificates = [System.Security.Cryptography.X509Certificates.X509CertificateCollection]::new([X509Certificate]$certificate)
+            $null = Invoke-WebRequest -Uri $uri -PreserveAuthorizationOnRedirect -WebSession $session -SkipCertificateCheck -Headers $headers
+            $session.Credentials.UserName | Should -BeExactly $credential.UserName
+            $session.Credentials.Password | Should -BeExactly $credential.GetNetworkCredential().Password
+            $session.Certificates.Thumbprint | Should -BeExactly $certificate.Thumbprint
+
+            $session = [Microsoft.PowerShell.Commands.WebRequestSession]::new()
+            $session.Proxy = [System.Net.WebProxy]::new($proxy)
+            $null = Invoke-WebRequest -Uri $uri -PreserveAuthorizationOnRedirect -WebSession $session -Headers $headers
+            $session.Proxy.GetProxy($uri).Authority | Should -BeExactly $proxy
+        }
+
         It "Validates Invoke-WebRequest strips the authorization header on various redirects: <redirectType>" -TestCases $redirectTests {
             param($redirectType)
             $uri = Get-WebListenerUrl -Test 'Redirect' -Query @{type = $redirectType}
@@ -2706,6 +2742,42 @@ Describe "Invoke-RestMethod tests" -Tags "Feature", "RequireAdminOnWindows" {
         $response.Content.Headers."Authorization" | Should -BeExactly "test"
     }
 
+    It "Validates Invoke-RestMethod with -WebSession and -PreserveAuthorizationOnRedirect doesn't change session variable on multiple redirects: <redirectType>" -TestCases $redirectTests {
+        param($redirectType)
+
+        #[SuppressMessage("Microsoft.Security", "CS002:SecretInNextLine", Justification="Demo/doc/test secret.")]
+        $token = "testpassword" | ConvertTo-SecureString -AsPlainText -Force
+        $credential = [pscredential]::new("testuser", $token)
+        $certificate = Get-WebListenerClientCertificate
+        $headers = @{"Authorization" = "test"}
+        $proxy = (Get-WebListenerUrl).Authority
+        $uri = Get-WebListenerUrl -Test 'Redirect' -TestValue 2 -Query @{type = $redirectType}
+
+        $session = [Microsoft.PowerShell.Commands.WebRequestSession]::new()
+        $session.MaximumRedirection = 2
+        $session.MaximumRetryCount = 2
+        $session.RetryIntervalInSeconds = 2
+        $session.UseDefaultCredentials = $true
+        $null = Invoke-RestMethod -Uri $uri -PreserveAuthorizationOnRedirect -WebSession $session -AllowUnencryptedAuthentication -Headers $headers
+        $session.MaximumRedirection | Should -BeExactly 2
+        $session.MaximumRetryCount | Should -BeExactly 2
+        $session.RetryIntervalInSeconds | Should -BeExactly 2
+        $session.UseDefaultCredentials | Should -BeExactly $true
+
+        $session = [Microsoft.PowerShell.Commands.WebRequestSession]::new()
+        $session.Credentials = $credential
+        $session.Certificates = [System.Security.Cryptography.X509Certificates.X509CertificateCollection]::new([X509Certificate]$certificate)
+        $null = Invoke-RestMethod -Uri $uri -PreserveAuthorizationOnRedirect -WebSession $session -SkipCertificateCheck -Headers $headers
+        $session.Credentials.UserName | Should -BeExactly $credential.UserName
+        $session.Credentials.Password | Should -BeExactly $credential.GetNetworkCredential().Password
+        $session.Certificates.Thumbprint | Should -BeExactly $certificate.Thumbprint
+
+        $session = [Microsoft.PowerShell.Commands.WebRequestSession]::new()
+        $session.Proxy = [System.Net.WebProxy]::new($proxy)
+        $null = Invoke-RestMethod -Uri $uri -PreserveAuthorizationOnRedirect -WebSession $session -Headers $headers
+        $session.Proxy.GetProxy($uri).Authority | Should -BeExactly $proxy
+    }
+
     It "Validates Invoke-RestMethod strips the authorization header on various redirects: <redirectType>" -TestCases $redirectTests {
         param($redirectType)
         $uri = Get-WebListenerUrl -Test 'Redirect' -Query @{type = $redirectType}