Nat,
Thanks for the reply. I could get the packet trace, but thinking about it, I am not sure which side I should trace? The outside interface is just recieving standard traffic and TLS negotiation, though maybe I would want to compare what a "working" client like checktls or Outlook does compared to non-working OpenSSL client.
If I capture on the inside, I would just capture the odd traffic that gets sent to the SMTP server, which is already in my SMTP logs, which doesn't really help either.
If you look back, the OP was talking about a "250 chunking" return when trying to get TLS negotiation working, do you see those posts in this thread? I am wondering what the actual problem with the iRule was there, because I seem to be having it with some SMTP clients even with the latest version posted here.
It seems the problem is inside the logic of the iRule, I'm not sure how to get to what the problem is there, other than logically working through the iRule in my mind, which hasn't worked out well so far ;-)
The SMTP server is an Exchange 2007 HUB server. I could easily put another type of SMTP server behind that pool to test if it is an interaction specific to the Exchange 2007 server.