STARTTLS - sendmail - outlook

[Vu Pham]

I am trying to recompile sendmail 8.12.9 in order to use Outlook with SSL.
After compiling, sendmail does show the 250-STARTTLS under the EHLO
greeting.

But when I set my Outlook to use SSL for sending, then it ( Outlook ) just
hangs right when it is trying to send.
/var/log/maillog does not show anything at that time.

Any idea where I can look at ?

( Cyrus Imap with SSL is working, so the OpenSsl has no problem in the mail
server ).

Thanks,

Vu