http://bugs.winehq.org/show_bug.cgi?id=30931
--- Comment #8 from Juan Lang juan.lang@gmail.com 2012-06-17 16:01:58 CDT --- (In reply to comment #6)
Since Newsbin has SSL built in with no external dependencies (that I'm aware of) and it works perfectly well with this version of SSL under windows, I'm skeptical that it has anything to do with the SSL version. If it depended on Windows to handle the SSL, then I'd agres.
Logically this argument doesn't follow. Things that work under Windows often don't work under Wine, so their working on Windows does not allow us to infer anything about their expected behavior under Wine. I agree that it's probably unlikely, but I know that, without investigation, we can't eliminate the possibility that the Windows version of openssl you use won't work when run under Wine.
I guess the question is, does wine do anything different with TCP connections on SSL ports than it does with other TCP connections?
No.
Welcome to the wonderful world of debugging under Wine: it's often complicated ;)