I'm running a C# web-scrapper application (that I wrote) on a Windows Server 2003 instance under a user belonging to the local Administrator group. When I run it within a desktop/remote-desktop session the application runs successfully but when I schedule it to run under the same user/security-context outside of the desktop session, all socket connections timeout. The scheduled task calls a batch file which in-turn calls the application. The Windows Server 2003 instance has a very basic configuration and isn't even connected to a domain. I cannot find anything in any firewall or security configuration which is preventing this but maybe I have overlooked something, can anyone be of any assistance? System.Net.WebException: Unable to connect to the remote server --- System.Net.Sockets.SocketException: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond X.X.X.X:443 at System.Net.Sockets.Socket.DoConnect(EndPoint endPointSnapshot, SocketAddress socketAddress) at System.Net.ServicePoint.ConnectSocketInternal(Boolean connectFailure, Socket s4, Socket s6, Socket& socket, IPAddress& address, ConnectSocketState state, IAsyncResult asyncResult, Int32 timeout, Exception& exception) --- End of inner exception stack trace --- at System.Net.HttpWebRequest.GetResponse()