On Tue, Feb 11, 2014 at 09:48:03AM -0800, fleon wrote: > After EHLO i now get: > AUTH NTLM LOGIN > > So i tried with login and it requested my username and password in base64. > > After typing then manually encoded, i got a RENEGOTIATING and finally a > handshake failure. Don't know if it's because i typed the username in wrong > format or if just it didn't like the certificate.
openssl s_client is testing tool, not a netcat replacement. It processes "R" at the beginning of a line as an SSL re-negotiate request. If you enable TLS in Postfix, it should be able to use "LOGIN", and you'll be all set. The username will likely work without any domain, but you can try a few formats if a bare username does not work. -- Viktor.