The program in question is an accounting software called Deltek Vision. Its built on .Net and communicates to an sql database on a server. The errors we are getting happen at random and consist of " error 400 bad request" or " the underlying connection was closed". After weeks of troubleshooting with their support. They claim we are losing connection or dropping packets. I see no evidence of either one. So I decided to put Fiddler on the client, when I did I no longer had the issue. Ive narrowed it down to Windows 7 machines only. The server is a VM running 2008r2.