On Nov 19, 2013, at 5:50, bitozoid <bitoz...@gmail.com> wrote: > > I'm getting a TLS timeout (4.4.2) when connecting to the smarthost > (port 465).
Port 465 is a legacy port and was only ever used by Outlook, as I recall. It is generally not supported by other MUAs, and I seriously doubt any MUA that is using it will support much of anything beyond the default Outlook methods for securing port 465. For example, it wouldn't support STARTTLS still is should be initiating an SSL connection from the start. Ther is no reason to use ports 465 unless you are supporting Windows95 users using Outlook (which can't use port 587, or at least not easily). Port 465 was actually reassigned for something to do with SMS and the use of it for email was deprecated 15-20 years ago.
