diff --git a/src/Titanium.Web.Proxy/EventArguments/SessionEventArgsBase.cs b/src/Titanium.Web.Proxy/EventArguments/SessionEventArgsBase.cs
index 98d22c74a..07fc38536 100644
--- a/src/Titanium.Web.Proxy/EventArguments/SessionEventArgsBase.cs
+++ b/src/Titanium.Web.Proxy/EventArguments/SessionEventArgsBase.cs
@@ -22,7 +22,7 @@ public abstract class SessionEventArgsBase : EventArgs, IDisposable
     {
         private static bool isWindowsAuthenticationSupported => RunTime.IsWindows;
 
-        internal readonly CancellationTokenSource CancellationTokenSource;
+        internal readonly CancellationTokenSource? CancellationTokenSource;
 
         internal TcpServerConnection ServerConnection => HttpClient.Connection;
 
diff --git a/src/Titanium.Web.Proxy/Helpers/RunTime.cs b/src/Titanium.Web.Proxy/Helpers/RunTime.cs
index b2d1e9847..a03cbbb7f 100644
--- a/src/Titanium.Web.Proxy/Helpers/RunTime.cs
+++ b/src/Titanium.Web.Proxy/Helpers/RunTime.cs
@@ -1,6 +1,8 @@
-using System;
+using System;
+using System.Reflection;
 using System.Text;
 using System.Runtime.InteropServices;
+using System.Runtime.Versioning;
 
 namespace Titanium.Web.Proxy.Helpers
 {
@@ -41,6 +43,62 @@ public static class RunTime
         public static bool IsUwpOnWindows => IsWindows && UwpHelper.IsRunningAsUwp();
 
         public static bool IsMac => isRunningOnMac;
+        
+        /// <summary>
+        /// Is socket reuse available to use?
+        /// </summary>
+        public static bool IsSocketReuseAvailable => isSocketReuseAvailable();
+
+        private static bool? _isSocketReuseAvailable;
+
+        private static bool isSocketReuseAvailable()
+        {
+            // use the cached value if we have one
+            if (_isSocketReuseAvailable != null)
+                return _isSocketReuseAvailable.Value;
+
+            try
+            {
+                if (IsWindows)
+                {
+                    // since we are on windows just return true
+                    // store the result in our static object so we don't have to be bothered going through all this more than once
+                    _isSocketReuseAvailable = true;
+                    return true;
+                }
+
+                // get the currently running framework name and version (EX: .NETFramework,Version=v4.5.1) (Ex: .NETCoreApp,Version=v2.0)
+                string ver = Assembly.GetEntryAssembly()?.GetCustomAttribute<TargetFrameworkAttribute>()?.FrameworkName;
+
+                if (ver == null)
+                    return false; // play it safe if we can not figure out what the framework is
+
+                // make sure we are on .NETCoreApp
+                ver = ver.ToLower(); // make everything lowercase to simplify comparison
+                if (ver.Contains(".netcoreapp"))
+                {
+                    var versionString = ver.Replace(".netcoreapp,version=v", "");
+                    var versionArr = versionString.Split('.');
+                    var majorVersion = Convert.ToInt32(versionArr[0]);
+
+                    var result = majorVersion >= 3; // version 3 and up supports socket reuse
+
+                    // store the result in our static object so we don't have to be bothered going through all this more than once
+                    _isSocketReuseAvailable = result;
+                    return result;
+                }
+
+                // store the result in our static object so we don't have to be bothered going through all this more than once
+                _isSocketReuseAvailable = false;
+                return false;
+            }
+            catch
+            {
+                // store the result in our static object so we don't have to be bothered going through all this more than once
+                _isSocketReuseAvailable = false;
+                return false;
+            }
+        }
 
         // https://github.com/qmatteoq/DesktopBridgeHelpers/blob/master/DesktopBridge.Helpers/Helpers.cs
         private class UwpHelper
diff --git a/src/Titanium.Web.Proxy/Network/Tcp/TcpConnectionFactory.cs b/src/Titanium.Web.Proxy/Network/Tcp/TcpConnectionFactory.cs
index b65b554f4..8f45b0608 100644
--- a/src/Titanium.Web.Proxy/Network/Tcp/TcpConnectionFactory.cs
+++ b/src/Titanium.Web.Proxy/Network/Tcp/TcpConnectionFactory.cs
@@ -315,8 +315,7 @@ private async Task<TcpServerConnection> createServerConnection(string remoteHost
                         tcpClient.SendTimeout = proxyServer.ConnectionTimeOutSeconds * 1000;
                         tcpClient.LingerState = new LingerOption(true, proxyServer.TcpTimeWaitSeconds);
 
-                        // linux has a bug with socket reuse in .net core.
-                        if (proxyServer.ReuseSocket && RunTime.IsWindows)
+                        if (proxyServer.ReuseSocket && RunTime.IsSocketReuseAvailable)
                         {
                             tcpClient.Client.SetSocketOption(SocketOptionLevel.Socket, SocketOptionName.ReuseAddress, true);
                         }
@@ -417,7 +416,7 @@ private async Task<TcpServerConnection> createServerConnection(string remoteHost
                 throw;
             }
 
-            return new TcpServerConnection(proxyServer, tcpClient)
+            return new TcpServerConnection(proxyServer, tcpClient, stream)
             {
                 UpStreamProxy = externalProxy,
                 UpStreamEndPoint = upStreamEndPoint,
@@ -426,8 +425,6 @@ private async Task<TcpServerConnection> createServerConnection(string remoteHost
                 IsHttps = isHttps,
                 NegotiatedApplicationProtocol = negotiatedApplicationProtocol,
                 UseUpstreamProxy = useUpstreamProxy,
-                StreamWriter = new HttpRequestWriter(stream, proxyServer.BufferPool),
-                Stream = stream,
                 Version = httpVersion
             };
         }
diff --git a/src/Titanium.Web.Proxy/Network/Tcp/TcpServerConnection.cs b/src/Titanium.Web.Proxy/Network/Tcp/TcpServerConnection.cs
index 62276d8ca..d6a0e7e81 100644
--- a/src/Titanium.Web.Proxy/Network/Tcp/TcpServerConnection.cs
+++ b/src/Titanium.Web.Proxy/Network/Tcp/TcpServerConnection.cs
@@ -15,12 +15,14 @@ namespace Titanium.Web.Proxy.Network.Tcp
     /// </summary>
     internal class TcpServerConnection : IDisposable
     {
-        internal TcpServerConnection(ProxyServer proxyServer, TcpClient tcpClient)
+        internal TcpServerConnection(ProxyServer proxyServer, TcpClient tcpClient, CustomBufferedStream stream)
         {
             this.tcpClient = tcpClient;
             LastAccess = DateTime.Now;
             this.proxyServer = proxyServer;
             this.proxyServer.UpdateServerConnectionCount(true);
+            StreamWriter = new HttpRequestWriter(stream, proxyServer.BufferPool);
+            Stream = stream;
         }
 
         private ProxyServer proxyServer { get; }
@@ -59,12 +61,12 @@ internal TcpServerConnection(ProxyServer proxyServer, TcpClient tcpClient)
         /// <summary>
         ///     Used to write lines to server
         /// </summary>
-        internal HttpRequestWriter? StreamWriter { get; set; }
+        internal HttpRequestWriter StreamWriter { get; }
 
         /// <summary>
         ///     Server stream
         /// </summary>
-        internal CustomBufferedStream? Stream { get; set; }
+        internal CustomBufferedStream Stream { get; }
 
         /// <summary>
         ///     Last time this connection was used
diff --git a/src/Titanium.Web.Proxy/ProxyServer.cs b/src/Titanium.Web.Proxy/ProxyServer.cs
index d7d89eb7e..0126a9358 100644
--- a/src/Titanium.Web.Proxy/ProxyServer.cs
+++ b/src/Titanium.Web.Proxy/ProxyServer.cs
@@ -55,7 +55,7 @@ public partial class ProxyServer : IDisposable
         /// <summary>
         ///     Upstream proxy manager.
         /// </summary>
-        private WinHttpWebProxyFinder systemProxyResolver;
+        private WinHttpWebProxyFinder? systemProxyResolver;
 
         
         /// <inheritdoc />
@@ -421,7 +421,7 @@ public void SetAsSystemHttpsProxy(ExplicitProxyEndPoint endPoint)
         /// <param name="protocolType">The proxy protocol type.</param>
         public void SetAsSystemProxy(ExplicitProxyEndPoint endPoint, ProxyProtocolType protocolType)
         {
-            if (!RunTime.IsWindows)
+            if (systemProxySettingsManager == null)
             {
                 throw new NotSupportedException(@"Setting system proxy settings are only supported in Windows.
                             Please manually confugure you operating system to use this proxy's port and address.");
@@ -515,7 +515,7 @@ public void DisableSystemHttpsProxy()
         /// </summary>
         public void RestoreOriginalProxySettings()
         {
-            if (!RunTime.IsWindows)
+            if (systemProxySettingsManager == null)
             {
                 throw new NotSupportedException(@"Setting system proxy settings are only supported in Windows.
                             Please manually configure your operating system to use this proxy's port and address.");
@@ -529,7 +529,7 @@ public void RestoreOriginalProxySettings()
         /// </summary>
         public void DisableSystemProxy(ProxyProtocolType protocolType)
         {
-            if (!RunTime.IsWindows)
+            if (systemProxySettingsManager == null)
             {
                 throw new NotSupportedException(@"Setting system proxy settings are only supported in Windows.
                             Please manually configure your operating system to use this proxy's port and address.");
@@ -543,7 +543,7 @@ public void DisableSystemProxy(ProxyProtocolType protocolType)
         /// </summary>
         public void DisableAllSystemProxies()
         {
-            if (!RunTime.IsWindows)
+            if (systemProxySettingsManager == null)
             {
                 throw new NotSupportedException(@"Setting system proxy settings are only supported in Windows.
                             Please manually confugure you operating system to use this proxy's port and address.");
@@ -622,7 +622,7 @@ public void Stop()
                 throw new Exception("Proxy is not running.");
             }
 
-            if (RunTime.IsWindows && !RunTime.IsUwpOnWindows)
+            if (systemProxySettingsManager != null)
             {
                 bool setAsSystemProxy = ProxyEndPoints.OfType<ExplicitProxyEndPoint>()
                     .Any(x => x.IsSystemHttpProxy || x.IsSystemHttpsProxy);
@@ -654,8 +654,7 @@ private void listen(ProxyEndPoint endPoint)
         {
             endPoint.Listener = new TcpListener(endPoint.IpAddress, endPoint.Port);
 
-            // linux/macOS has a bug with socket reuse in .net core.
-            if (ReuseSocket && RunTime.IsWindows)
+            if (ReuseSocket && RunTime.IsSocketReuseAvailable)
             {
                 endPoint.Listener.Server.SetSocketOption(SocketOptionLevel.Socket, SocketOptionName.ReuseAddress, true);
             }