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 60ee931591a..0cc82345d5c 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
@@ -958,28 +958,25 @@ internal virtual void PrepareSession()
             {
                 WebSession.NoProxy = true;
             }
-            else
+            else if (Proxy is not null)
             {
-                if (Proxy is not null)
+                WebProxy webProxy = new(Proxy);
+
+                if (ProxyCredential is not null)
                 {
-                    WebProxy webProxy = new(Proxy);
-                    webProxy.BypassProxyOnLocal = false;
-                    if (ProxyCredential is not null)
-                    {
-                        webProxy.Credentials = ProxyCredential.GetNetworkCredential();
-                    }
-                    else
-                    {
-                        webProxy.UseDefaultCredentials =  ProxyUseDefaultCredentials;
-                    }
+                    webProxy.Credentials = ProxyCredential.GetNetworkCredential();
+                }
+                else
+                {
+                    webProxy.UseDefaultCredentials =  ProxyUseDefaultCredentials;
+                }
 
-                    // We don't want to update the WebSession unless the proxies are different
-                    // as that will require us to create a new HttpClientHandler and lose connection
-                    // persistence.
-                    if (!webProxy.Equals(WebSession.Proxy))
-                    {
-                        WebSession.Proxy = webProxy;
-                    }
+                // We don't want to update the WebSession unless the proxies are different
+                // as that will require us to create a new HttpClientHandler and lose connection
+                // persistence.
+                if (!webProxy.Equals(WebSession.Proxy))
+                {
+                    WebSession.Proxy = webProxy;
                 }
             }
 
diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebProxy.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebProxy.cs
index 6e9f6bdf98e..e806b595a55 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebProxy.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebProxy.cs
@@ -4,25 +4,21 @@
 #nullable enable
 
 using System;
-using System.Net;
+using System.Collections;
+using System.Collections.Generic;
 
 namespace Microsoft.PowerShell.Commands
 {
-    internal class WebProxy : IWebProxy, IEquatable<WebProxy>
+    internal class WebProxy : System.Net.WebProxy, IEquatable<WebProxy>
     {
-        private ICredentials? _credentials;
-        private readonly Uri _proxyAddress;
-
-        internal WebProxy(Uri address)
+        internal WebProxy(Uri? address)
         {
-            ArgumentNullException.ThrowIfNull(address);
-
-            _proxyAddress = address;
+            Address = address;
         }
 
         public override bool Equals(object? obj) => Equals(obj as WebProxy);
 
-        public override int GetHashCode() => HashCode.Combine(_proxyAddress, _credentials, BypassProxyOnLocal);
+        public override int GetHashCode() => HashCode.Combine(Address, Credentials, BypassProxyOnLocal);
 
         public bool Equals(WebProxy? other)
         {
@@ -30,36 +26,12 @@ public bool Equals(WebProxy? other)
             {
                 return false;
             }
-
-            // _proxyAddress cannot be null as it is set in the constructor            
-            return other._credentials == _credentials
-                && _proxyAddress.Equals(other._proxyAddress)
-                && BypassProxyOnLocal == other.BypassProxyOnLocal;
+      
+            return Address == other.Address
+                   && Credentials == other.Credentials
+                   && BypassProxyOnLocal == other.BypassProxyOnLocal
+                   && UseDefaultCredentials == other.UseDefaultCredentials
+                   && (BypassList as IStructuralEquatable).Equals(other.BypassList, EqualityComparer<string>.Default);
         }
-
-        public ICredentials? Credentials
-        {
-            get => _credentials;
-
-            set => _credentials = value;
-        }
-
-        internal bool BypassProxyOnLocal { get; set; }
-
-        internal bool UseDefaultCredentials
-        {
-            get => _credentials == CredentialCache.DefaultCredentials;
-
-            set => _credentials = value ? CredentialCache.DefaultCredentials : null;
-        }
-
-        public Uri GetProxy(Uri destination)
-        {
-            ArgumentNullException.ThrowIfNull(destination);
-
-            return destination.IsLoopback ? destination : _proxyAddress;
-        }
-
-        public bool IsBypassed(Uri host) => host.IsLoopback;
     }
 }