diff --git a/examples/Titanium.Web.Proxy.Examples.Basic/ProxyTestController.cs b/examples/Titanium.Web.Proxy.Examples.Basic/ProxyTestController.cs
index 1f9d3ed16..f7ffeb7b9 100644
--- a/examples/Titanium.Web.Proxy.Examples.Basic/ProxyTestController.cs
+++ b/examples/Titanium.Web.Proxy.Examples.Basic/ProxyTestController.cs
@@ -207,6 +207,17 @@ private async Task onRequest(object sender, SessionEventArgs e)
         {
             e.GetState().PipelineInfo.AppendLine(nameof(onRequest) + ":" + e.HttpClient.Request.RequestUri);
 
+            var clientLocalIp = e.ClientLocalEndPoint.Address;
+            if (!clientLocalIp.Equals(IPAddress.Loopback) && !clientLocalIp.Equals(IPAddress.IPv6Loopback))
+            {
+                e.HttpClient.UpStreamEndPoint = new IPEndPoint(clientLocalIp, 0);
+            }
+
+            if (e.HttpClient.Request.Url.Contains("yahoo.com"))
+            {
+                e.CustomUpStreamProxy = new ExternalProxy("localhost", 8888);
+            }
+
             await writeToConsole("Active Client Connections:" + ((ProxyServer)sender).ClientConnectionCount);
             await writeToConsole(e.HttpClient.Request.Url);
 
diff --git a/src/Titanium.Web.Proxy/EventArguments/SessionEventArgsBase.cs b/src/Titanium.Web.Proxy/EventArguments/SessionEventArgsBase.cs
index 081ea4561..c362317ae 100644
--- a/src/Titanium.Web.Proxy/EventArguments/SessionEventArgsBase.cs
+++ b/src/Titanium.Web.Proxy/EventArguments/SessionEventArgsBase.cs
@@ -59,7 +59,7 @@ private protected SessionEventArgsBase(ProxyServer server, ProxyEndPoint endPoin
 
             ClientStream = clientStream;
             HttpClient = new HttpWebClient(connectRequest, request, new Lazy<int>(() => clientStream.Connection.GetProcessId(endPoint)));
-            LocalEndPoint = endPoint;
+            ProxyEndPoint = endPoint;
             EnableWinAuth = server.EnableWinAuth && isWindowsAuthenticationSupported;
         }
 
@@ -103,6 +103,9 @@ public bool EnableWinAuth
         /// </summary>
         public IPEndPoint ClientRemoteEndPoint => (IPEndPoint)ClientConnection.RemoteEndPoint;
 
+        [Obsolete("Use ClientRemoteEndPoint instead.")]
+        public IPEndPoint ClientEndPoint => ClientRemoteEndPoint;
+
         /// <summary>
         ///    The web client used to communicate with server for this session.
         /// </summary>
@@ -111,6 +114,14 @@ public bool EnableWinAuth
         [Obsolete("Use HttpClient instead.")]
         public HttpWebClient WebSession => HttpClient;
 
+        /// <summary>
+        ///     Gets or sets the custom up stream proxy.
+        /// </summary>
+        /// <value>
+        ///     The custom up stream proxy.
+        /// </value>
+        public IExternalProxy? CustomUpStreamProxy { get; set; }
+
         /// <summary>
         ///     Are we using a custom upstream HTTP(S) proxy?
         /// </summary>
@@ -119,12 +130,15 @@ public bool EnableWinAuth
         /// <summary>
         ///     Local endpoint via which we make the request.
         /// </summary>
-        public ProxyEndPoint LocalEndPoint { get; }
+        public ProxyEndPoint ProxyEndPoint { get; }
+
+        [Obsolete("Use ProxyEndPoint instead.")]
+        public ProxyEndPoint LocalEndPoint => ProxyEndPoint;
 
         /// <summary>
         ///     Is this a transparent endpoint?
         /// </summary>
-        public bool IsTransparent => LocalEndPoint is TransparentProxyEndPoint;
+        public bool IsTransparent => ProxyEndPoint is TransparentProxyEndPoint;
 
         /// <summary>
         ///     The last exception that happened.
diff --git a/src/Titanium.Web.Proxy/Helpers/WinHttp/WinHttpWebProxyFinder.cs b/src/Titanium.Web.Proxy/Helpers/WinHttp/WinHttpWebProxyFinder.cs
index 8b8ec3295..1aed46492 100644
--- a/src/Titanium.Web.Proxy/Helpers/WinHttp/WinHttpWebProxyFinder.cs
+++ b/src/Titanium.Web.Proxy/Helpers/WinHttp/WinHttpWebProxyFinder.cs
@@ -114,11 +114,7 @@ public bool GetAutoProxies(Uri destination, out IList<string>? proxyList)
                 }
 
                 // TODO: Apply authorization
-                var systemProxy = new ExternalProxy
-                {
-                    HostName = proxyStr,
-                    Port = port
-                };
+                var systemProxy = new ExternalProxy(proxyStr, port);
 
                 return systemProxy;
             }
@@ -134,12 +130,7 @@ public bool GetAutoProxies(Uri destination, out IList<string>? proxyList)
                 HttpSystemProxyValue? value = null;
                 if (ProxyInfo?.Proxies?.TryGetValue(protocolType.Value, out value) == true)
                 {
-                    var systemProxy = new ExternalProxy
-                    {
-                        HostName = value!.HostName,
-                        Port = value.Port
-                    };
-
+                    var systemProxy = new ExternalProxy(value!.HostName, value.Port);
                     return systemProxy;
                 }
             }
diff --git a/src/Titanium.Web.Proxy/Models/ExternalProxy.cs b/src/Titanium.Web.Proxy/Models/ExternalProxy.cs
index 931248233..70ae99caf 100644
--- a/src/Titanium.Web.Proxy/Models/ExternalProxy.cs
+++ b/src/Titanium.Web.Proxy/Models/ExternalProxy.cs
@@ -69,6 +69,39 @@ public string? Password
         /// </summary>
         public int Port { get; set; }
 
+        /// <summary>
+        ///     Initializes a new instance of the <see cref="ExternalProxy"/> class.
+        /// </summary>
+        public ExternalProxy()
+        {
+        }
+
+        /// <summary>
+        ///     Initializes a new instance of the <see cref="ExternalProxy"/> class.
+        /// </summary>
+        /// <param name="hostName">Name of the host.</param>
+        /// <param name="port">The port.</param>
+        public ExternalProxy(string hostName, int port)
+        {
+            HostName = hostName; 
+            Port = port;
+        }
+
+        /// <summary>
+        ///     Initializes a new instance of the <see cref="ExternalProxy"/> class.
+        /// </summary>
+        /// <param name="hostName">Name of the host.</param>
+        /// <param name="port">The port.</param>
+        /// <param name="userName">Name of the user.</param>
+        /// <param name="password">The password.</param>
+        public ExternalProxy(string hostName, int port, string userName, string password)
+        {
+            HostName = hostName;
+            Port = port;
+            UserName = userName;
+            Password = password;
+        }
+
         /// <summary>
         ///     returns data in Hostname:port format.
         /// </summary>
@@ -77,6 +110,5 @@ public override string ToString()
         {
             return $"{HostName}:{Port}";
         }
-
     }
 }
diff --git a/src/Titanium.Web.Proxy/Network/Tcp/TcpConnectionFactory.cs b/src/Titanium.Web.Proxy/Network/Tcp/TcpConnectionFactory.cs
index 1b507802f..62d9e935e 100644
--- a/src/Titanium.Web.Proxy/Network/Tcp/TcpConnectionFactory.cs
+++ b/src/Titanium.Web.Proxy/Network/Tcp/TcpConnectionFactory.cs
@@ -114,10 +114,10 @@ internal async Task<string> GetConnectionCacheKey(ProxyServer server, SessionEve
                 applicationProtocols = new List<SslApplicationProtocol> { applicationProtocol };
             }
 
-            IExternalProxy? customUpStreamProxy = null;
+            IExternalProxy? customUpStreamProxy = session.CustomUpStreamProxy;
 
             bool isHttps = session.IsHttps;
-            if (server.GetCustomUpStreamProxyFunc != null)
+            if (customUpStreamProxy == null && server.GetCustomUpStreamProxyFunc != null)
             {
                 customUpStreamProxy = await server.GetCustomUpStreamProxyFunc(session);
             }
@@ -169,10 +169,10 @@ internal Task<TcpServerConnection> GetServerConnection(ProxyServer proxyServer,
         internal async Task<TcpServerConnection> GetServerConnection(ProxyServer proxyServer, SessionEventArgsBase session, bool isConnect,
             List<SslApplicationProtocol>? applicationProtocols, bool noCache, CancellationToken cancellationToken)
         {
-            IExternalProxy? customUpStreamProxy = null;
+            IExternalProxy? customUpStreamProxy = session.CustomUpStreamProxy;
 
             bool isHttps = session.IsHttps;
-            if (proxyServer.GetCustomUpStreamProxyFunc != null)
+            if (customUpStreamProxy == null && proxyServer.GetCustomUpStreamProxyFunc != null)
             {
                 customUpStreamProxy = await proxyServer.GetCustomUpStreamProxyFunc(session);
             }
diff --git a/src/Titanium.Web.Proxy/WinAuthHandler.cs b/src/Titanium.Web.Proxy/WinAuthHandler.cs
index c72d333e1..4ea7bd073 100644
--- a/src/Titanium.Web.Proxy/WinAuthHandler.cs
+++ b/src/Titanium.Web.Proxy/WinAuthHandler.cs
@@ -175,7 +175,7 @@ private async Task rewriteUnauthorizedResponse(SessionEventArgs args)
             // Add custom div to body to clarify that the proxy (not the client browser) failed authentication
             string authErrorMessage =
                 "<div class=\"inserted-by-proxy\"><h2>NTLM authentication through Titanium.Web.Proxy (" +
-                args.ClientConnection.LocalEndPoint +
+                args.ClientLocalEndPoint +
                 ") failed. Please check credentials.</h2></div>";
             string originalErrorMessage =
                 "<div class=\"inserted-by-proxy\"><h3>Response from remote web server below.</h3></div><br/>";
diff --git a/tests/Titanium.Web.Proxy.IntegrationTests/NestedProxyTests.cs b/tests/Titanium.Web.Proxy.IntegrationTests/NestedProxyTests.cs
index 3f1f8a2ca..ef2c088a9 100644
--- a/tests/Titanium.Web.Proxy.IntegrationTests/NestedProxyTests.cs
+++ b/tests/Titanium.Web.Proxy.IntegrationTests/NestedProxyTests.cs
@@ -59,11 +59,7 @@ public async Task Smoke_Test_Nested_Proxy_UserData()
             {
                 Assert.AreEqual("Test", session.UserData);
 
-                return await Task.FromResult(new Models.ExternalProxy
-                {
-                    HostName = "localhost",
-                    Port = proxy2.ProxyEndPoints[0].Port
-                });
+                return await Task.FromResult(new Models.ExternalProxy("localhost", proxy2.ProxyEndPoints[0].Port));
             };
 
             var client = testSuite.GetClient(proxy1, true);
diff --git a/tests/Titanium.Web.Proxy.IntegrationTests/Setup/TestProxyServer.cs b/tests/Titanium.Web.Proxy.IntegrationTests/Setup/TestProxyServer.cs
index 7a8d80c3d..d85ef4240 100644
--- a/tests/Titanium.Web.Proxy.IntegrationTests/Setup/TestProxyServer.cs
+++ b/tests/Titanium.Web.Proxy.IntegrationTests/Setup/TestProxyServer.cs
@@ -22,17 +22,8 @@ public TestProxyServer(bool isReverseProxy, ProxyServer upStreamProxy = null)
 
             if (upStreamProxy != null)
             {
-                ProxyServer.UpStreamHttpProxy = new ExternalProxy
-                {
-                    HostName = "localhost",
-                    Port = upStreamProxy.ProxyEndPoints[0].Port
-                };
-
-                ProxyServer.UpStreamHttpsProxy = new ExternalProxy
-                {
-                    HostName = "localhost",
-                    Port = upStreamProxy.ProxyEndPoints[0].Port
-                };
+                ProxyServer.UpStreamHttpProxy = new ExternalProxy("localhost", upStreamProxy.ProxyEndPoints[0].Port);
+                ProxyServer.UpStreamHttpsProxy = new ExternalProxy("localhost", upStreamProxy.ProxyEndPoints[0].Port);
             }
 
             ProxyServer.Start();