Take the 2-minute tour ×  I set up a server running Postfix +
Dovecot w/ SASL auth and SSL everywhere (actually, STARTTLS).
It's about as "bog-standard" as you can get (meaning I followed
one of the innumerable cookbooks on the topic).  My outbound
SMTP uses port 587 and IMAP is on 993. The auth mechanism is
PLAIN. Like I said, STARTTLS everywhere.  Connections work fine
- sending and receving - and as expected in: Postbox,
Thunderbird, Mail Pilot, Mailmate, Airmail (all on Mavericks),
iOS 7, whatever the recent Android candy flavor is, and
Thunderbird on Windows 7.  Mail.app will not connect. It throws
the warning triangle up immediately when you start Mail.
Connection Doctor shows 'INITIATING CONNECTION' and the host IP
with some hex strings but no other information.  Now here's the
rub: before starting any mail client, I started a tcpdump
filtering on the destination address. If I start any other mail
client, or just do openssl s_client -connect to the server
address, I see packets flowing from here to the