http://bugs.winehq.org/show_bug.cgi?id=21096
--- Comment #30 from Juan Lang juan_lang@yahoo.com 2010-09-28 15:25:22 CDT --- (In reply to comment #27)
The certificate was one I generated for just this purpose (Azureus has you generate one before setting up an https tracker).
Actually, this is probably the interesting part. Could you attach a +crypt log of this? It could be that the app installs the certificate into a local "certificate store", but since OpenSSL doesn't check the crypt32 certificate stores, that's the reason the connection is failing. That would make the scope of this bug pretty large, but still valid.