I am working on a Windows Server 2008 box. I have a console app that I'm using to test the handshake between myself and another server. When I build this app under .net4.0 the connection is fine, but when I build the same app under 3.5 the connection will timeout.
One thing I found out is when I use fiddler on the 3.5 app, when I have fiddler "DECRYPT HTTPS TRAFFIC" the handshake goes through just fine, but if this box is not checked it will timeout as usual.
I have a feeling it has something to do with the ciphers and the way .net 3.5 uses them vs .net 4.0.
Has anybody ran into this issue before?
Sharing a NetMon or Wireshark (pcap) trace will help resolve this.
With HTTPS decryption disabled in Fiddler, compare the text of the Request TextView inspector for the CONNECT tunnels from the working and non-working application. Are different ciphers offered?
It's possible that you're hitting something like this: http://blogs.msdn.com/b/fiddler/archive/2012/03/29/https-request-hangs-.net-application-connection-on-tls-server-name-indicator-warning.aspx