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[Lee Dilkie]

>-----Original Message-----
>From: owner-freebsd-questions at freebsd.org
>[mailto:owner-freebsd-questions at freebsd.org]On Behalf Of Richard
>Stevenson
>Outlook 2002 (from Office XP) will try STARTTLS if 
>SMTP-over-SSL doesn't 
>work for any port other than 25, apparently, but as I said, 
>it's still a 
>bit hairy.  I've got clients in .us, .uk, and .nz doing this with my 
>server in .nz.  FWIW, I believe Microsoft are still working on 
>this - I'm 
>told they might default to trying STARTTLS first for port 587.  These 
>things take time; the MSA standard is only about five years old, after 
>all...

Wow, that responsive? The only hitch is that office 2K is my last version of office (as win2K is my last version of a MS OS that'll I'll buy).

It was a challange to cover all the bases, between outlook [express] and others (Kmail, Evolution...) I have running:

25 - smtp (with or w/o auth), w/STARTTLS
587 - MSA (auth SMTP), w/ STARTTLS
465 - smtps (with or w/o auth), SSL
110 - pop3, w/STARTTLS
*996 (not 995!) - pop3s, SSL
143 - imap (don't think that supports STARTTLS)
993 - imaps, SSL

I'm using qpopper for pop3 and imap-uw for imap and sendmail for the rest. I installed cyrus-sasl to provide decent password protection on the non-ssl'ed connections.

*996 instead of 995... this was a wierd one. Outlook normally defaults to port 995 if one selects "use SSL" but when I configured qpopper to use SSL on 995 the negotation would fail. If i changed ports, it succeeded. I think I know what happened and that I could probably get it to work on 995 but I haven't had the time to work on it.

I config Outlook to use SSL on ports 465 and either 996(pop3) or 993(imap). Kmail and such use 587(MSA) and 110/993 as they support STARTTLS.
 
If anyone is interested in the relevant bits of inetd/sendmail/qpopper config files, just shout.

-lee