diff --git a/src/Titanium.Web.Proxy/Exceptions/ServerConnectionException.cs b/src/Titanium.Web.Proxy/Exceptions/RetryableServerConnectionException.cs
similarity index 51%
rename from src/Titanium.Web.Proxy/Exceptions/ServerConnectionException.cs
rename to src/Titanium.Web.Proxy/Exceptions/RetryableServerConnectionException.cs
index d885c74e7..ad07df990 100644
--- a/src/Titanium.Web.Proxy/Exceptions/ServerConnectionException.cs
+++ b/src/Titanium.Web.Proxy/Exceptions/RetryableServerConnectionException.cs
@@ -3,12 +3,12 @@
 namespace Titanium.Web.Proxy.Exceptions
 {
     /// <summary>
-    /// The server connection was closed upon first read with the new connection from pool.
+    /// The server connection was closed upon first write with the new connection from pool.
     /// Should retry the request with a new connection.
     /// </summary>
-    public class ServerConnectionException : ProxyException
+    public class RetryableServerConnectionException : ProxyException
     {
-        internal ServerConnectionException(string message) : base(message)
+        internal RetryableServerConnectionException(string message) : base(message)
         {
         }
 
@@ -17,9 +17,8 @@ internal ServerConnectionException(string message) : base(message)
         /// </summary>
         /// <param name="message"></param>
         /// <param name="e"></param>
-        internal ServerConnectionException(string message, Exception e) : base(message, e)
+        internal RetryableServerConnectionException(string message, Exception e) : base(message, e)
         {
         }
-
     }
 }
diff --git a/src/Titanium.Web.Proxy/Network/RetryPolicy.cs b/src/Titanium.Web.Proxy/Network/RetryPolicy.cs
index a2f724554..19863cba0 100644
--- a/src/Titanium.Web.Proxy/Network/RetryPolicy.cs
+++ b/src/Titanium.Web.Proxy/Network/RetryPolicy.cs
@@ -35,14 +35,12 @@ internal async Task<RetryResult> ExecuteAsync(Func<TcpServerConnection, Task<boo
 
             while (true)
             {
+                // setup connection
+                currentConnection ??= await generator();
+
                 try
                 {
-                    // setup connection
-                    currentConnection ??= await generator();
-
-                    // try
                     @continue = await action(currentConnection);
-
                 }
                 catch (Exception ex)
                 {
diff --git a/src/Titanium.Web.Proxy/Network/Streams/HttpServerStream.cs b/src/Titanium.Web.Proxy/Network/Streams/HttpServerStream.cs
index 5b95e9c1c..a646d64b8 100644
--- a/src/Titanium.Web.Proxy/Network/Streams/HttpServerStream.cs
+++ b/src/Titanium.Web.Proxy/Network/Streams/HttpServerStream.cs
@@ -30,25 +30,19 @@ internal async ValueTask WriteRequestAsync(Request request, CancellationToken ca
 
         internal async ValueTask<ResponseStatusInfo> ReadResponseStatus(CancellationToken cancellationToken = default)
         {
-            try
-            {
-                string httpStatus = await ReadLineAsync(cancellationToken) ??
-                                    throw new ServerConnectionException("Server connection was closed.");
-
-                if (httpStatus == string.Empty)
-                {
-                    // is this really possible?
-                    httpStatus = await ReadLineAsync(cancellationToken) ??
-                                 throw new ServerConnectionException("Server connection was closed. Response status is empty.");
-                }
+            string httpStatus = await ReadLineAsync(cancellationToken) ??
+                                throw new IOException("Invalid http status code.");
 
-                Response.ParseResponseLine(httpStatus, out var version, out int statusCode, out string description);
-                return new ResponseStatusInfo { Version = version, StatusCode = statusCode, Description = description };
-            }
-            catch (Exception e) when (!(e is ServerConnectionException))
+            if (httpStatus == string.Empty)
             {
-                throw new ServerConnectionException("Server connection was closed. Exception while reading the response status.", e);
+                // is this really possible?
+                httpStatus = await ReadLineAsync(cancellationToken) ??
+                             throw new IOException("Response status is empty.");
             }
+
+            Response.ParseResponseLine(httpStatus, out var version, out int statusCode, out string description);
+            return new ResponseStatusInfo { Version = version, StatusCode = statusCode, Description = description };
+
         }
     }
 }
diff --git a/src/Titanium.Web.Proxy/Network/Streams/HttpStream.cs b/src/Titanium.Web.Proxy/Network/Streams/HttpStream.cs
index 3f4e2f75b..9e38996ee 100644
--- a/src/Titanium.Web.Proxy/Network/Streams/HttpStream.cs
+++ b/src/Titanium.Web.Proxy/Network/Streams/HttpStream.cs
@@ -932,7 +932,21 @@ public ValueTask WriteLineAsync(string value, CancellationToken cancellationToke
         internal async Task WriteHeadersAsync(HeaderBuilder headerBuilder, CancellationToken cancellationToken = default)
         {
             var buffer = headerBuilder.GetBuffer();
-            await WriteAsync(buffer.Array, buffer.Offset, buffer.Count, true, cancellationToken);
+
+            try
+            {
+                await WriteAsync(buffer.Array, buffer.Offset, buffer.Count, true, cancellationToken);
+            }
+            catch (IOException e)
+            {
+                //throw this as ServerConnectionException so that RetryPolicy can retry with a new server connection.
+                if (this is HttpServerStream)
+                {
+                    throw new RetryableServerConnectionException("Server connection was closed. Exception while sending request line and headers.", e);
+                }
+
+                throw;
+            }
         }
 
         /// <summary>
@@ -1226,7 +1240,6 @@ private async Task copyBytesToStream(IHttpStreamWriter writer, long count, bool
         protected async ValueTask WriteAsync(RequestResponseBase requestResponse, HeaderBuilder headerBuilder, CancellationToken cancellationToken = default)
         {
             var body = requestResponse.CompressBodyAndUpdateContentLength();
-
             headerBuilder.WriteHeaders(requestResponse.Headers);
             await WriteHeadersAsync(headerBuilder, cancellationToken);
 
diff --git a/src/Titanium.Web.Proxy/Network/TcpConnection/TcpConnectionFactory.cs b/src/Titanium.Web.Proxy/Network/TcpConnection/TcpConnectionFactory.cs
index 429e1dadc..5d1c433fb 100644
--- a/src/Titanium.Web.Proxy/Network/TcpConnection/TcpConnectionFactory.cs
+++ b/src/Titanium.Web.Proxy/Network/TcpConnection/TcpConnectionFactory.cs
@@ -520,15 +520,17 @@ internal Task<TcpServerConnection> GetServerConnection(ProxyServer proxyServer,
 
                 if (externalProxy != null && externalProxy.ProxyType == ExternalProxyType.Http && (isConnect || isHttps))
                 {
-                    var authority = $"{remoteHostName}:{remotePort}".GetByteString();
-                    var connectRequest = new ConnectRequest(authority)
+                    var authority = $"{remoteHostName}:{remotePort}";
+                    var authorityBytes = authority.GetByteString();
+                    var connectRequest = new ConnectRequest(authorityBytes)
                     {
                         IsHttps = isHttps,
-                        RequestUriString8 = authority,
+                        RequestUriString8 = authorityBytes,
                         HttpVersion = httpVersion
                     };
 
                     connectRequest.Headers.AddHeader(KnownHeaders.Connection, KnownHeaders.ConnectionKeepAlive);
+                    connectRequest.Headers.AddHeader(KnownHeaders.Host, authority);
 
                     if (!string.IsNullOrEmpty(externalProxy.UserName) && externalProxy.Password != null)
                     {
diff --git a/src/Titanium.Web.Proxy/ProxyServer.cs b/src/Titanium.Web.Proxy/ProxyServer.cs
index 377e31d6a..a0bca42c0 100644
--- a/src/Titanium.Web.Proxy/ProxyServer.cs
+++ b/src/Titanium.Web.Proxy/ProxyServer.cs
@@ -123,7 +123,7 @@ public ProxyServer(string? rootCertificateName, string? rootCertificateIssuerNam
         /// <summary>
         ///     Number of times to retry upon network failures when connection pool is enabled.
         /// </summary>
-        public int NetworkFailureRetryAttempts { get; set; } = 0;
+        public int NetworkFailureRetryAttempts { get; set; } = 1;
 
         /// <summary>
         ///     Is the proxy currently running?
@@ -208,9 +208,9 @@ public ProxyServer(string? rootCertificateName, string? rootCertificateIssuerNam
         /// <summary>
         ///     Maximum number of concurrent connections per remote host in cache.
         ///     Only valid when connection pooling is enabled.
-        ///     Default value is 2.
+        ///     Default value is 4.
         /// </summary>
-        public int MaxCachedConnections { get; set; } = 2;
+        public int MaxCachedConnections { get; set; } = 4;
 
         /// <summary>
         ///     Number of seconds to linger when Tcp connection is in TIME_WAIT state.
diff --git a/src/Titanium.Web.Proxy/RequestHandler.cs b/src/Titanium.Web.Proxy/RequestHandler.cs
index 103f309f9..005c2daa7 100644
--- a/src/Titanium.Web.Proxy/RequestHandler.cs
+++ b/src/Titanium.Web.Proxy/RequestHandler.cs
@@ -288,8 +288,13 @@ private async Task<RetryResult> handleHttpSessionRequest(SessionEventArgs args,
                     noCache,
                     cancellationToken);
 
-            // for connection pool, retry fails until cache is exhausted.   
-            return await retryPolicy<ServerConnectionException>().ExecuteAsync(async connection =>
+            /// Retry with new connection if the initial stream.WriteAsync call to server fails.
+            /// i.e if request line and headers failed to get send.
+            /// Do not retry after reading data from client stream, 
+            /// because subsequent try will not have data to read from client 
+            /// and will hang at clientStream.ReadAsync call.
+            /// So, throw RetryableServerConnectionException only when we are sure we can retry safely.
+            return await retryPolicy<RetryableServerConnectionException>().ExecuteAsync(async connection =>
             {
                 // set the connection and send request headers
                 args.HttpClient.SetConnection(connection);
diff --git a/tests/Titanium.Web.Proxy.IntegrationTests/NestedProxyTests.cs b/tests/Titanium.Web.Proxy.IntegrationTests/NestedProxyTests.cs
index 84d23eadc..5a95aa8fd 100644
--- a/tests/Titanium.Web.Proxy.IntegrationTests/NestedProxyTests.cs
+++ b/tests/Titanium.Web.Proxy.IntegrationTests/NestedProxyTests.cs
@@ -202,7 +202,6 @@ public async Task Nested_Proxy_Farm_With_Connection_Cache_Should_Not_Hang()
                 {
                     return Task.FromResult(true);
                 };
-
                 proxies2.Add(proxy2);
             }
 
@@ -212,9 +211,7 @@ public async Task Nested_Proxy_Farm_With_Connection_Cache_Should_Not_Hang()
             for (int i = 0; i < 10; i++)
             {
                 var proxy1 = testSuite.GetProxy();
-                //proxy1.EnableConnectionPool = false;
                 var proxy2 = proxies2[rnd.Next() % proxies2.Count];
-
                 var explicitEndpoint = proxy1.ProxyEndPoints.OfType<ExplicitProxyEndPoint>().First();
                 explicitEndpoint.BeforeTunnelConnectRequest += (_, e) =>
                 {