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[Steven Champeon <schampeo AT hesketh.com>]

on Tue, Dec 19, 2006 at 03:34:27PM -0500, stan briggs wrote:
> the message in /var/log/maillog is:
> 
> Dec 14 13:56:35 pb1 sm-mta[32022]: STARTTLS=server, relay=[199.72.20.170],
> version=TLSv1/SSLv3, verify=NOT, cipher=DHE-RSA-AES256-SHA, bits=256/256

OK, you're trying to use SSL. But you say the server isn't? Are you
missing some log entries here?

> Dec 14 13:56:36 pb1 sm-mta[32022]: AUTH=server, relay=[199.72.20.170],
> authid=stan_sb, mech=PLAIN, bits=0

OK, you seem to have authenticated as stan_sb using mech PLAIN. Again,
looks like you're missing some log entries here; you should see something
like:

Dec 19 08:35:22 habanero sm-mta[1308]: kBJDZMo4001308: <-- AUTH CRAM-MD5
Dec 19 08:35:22 habanero sm-mta[1308]: kBJDZMo4001308: --- 334 {elided}
Dec 19 08:35:23 habanero sm-mta[1308]: kBJDZMo4001308: --- 235 2.0.0 OK
Authenticated

...before the line you include above, which indicates success, a la:

Dec 19 08:35:23 habanero sm-mta[1308]: AUTH=server,
relay=liam.hesketh.com [216.187.232.186], authid={elided},
mech=CRAM-MD5, bits=0

> Dec 14 13:56:36 pb1 sm-mta[32022]: kBEIuX3o032022: ruleset=check_rcpt,
> arg1=<stan AT itsco.com>, relay=[199.72.20.170], reject=550 5.7.1
> <stan AT itsco.com>... Relaying denied. IP name lookup failed
> [199.72.20.170]

Those are sendmail logs. And your mail is being refused because
199.72.20.170 doesn't have reverse DNS, so presumably sendmail is
configured to reject for that reason (a /really/ good idea for an MTA's
port 25, FWIW).

Are you using a submit.cf and requiring SMTP AUTH on port 587?

Otherwise, you're just pretending, rather poorly, to be an MTA, instead
of a mail /client/. If you require AUTH on port 587, you can make that
the only restriction, and relax your rDNS requirements (in essence, if
you can auth, you can send - solves any and all roaming issues at one
fell swoop). The submit.mc file is /really/ brain-dead simple.
 
> 3. Are you using SSL?
> 
> no, the outgoing smtp server is set to not do so. the incoming server
> is set to do so.

See above (STARTTLS is "transport level security", or SSL). Why are
you trying to use SSL with a server that doesn't support it?
 
> 'SSL' is selected. 'Use secure authentication' is not.

Unselect SSL :) Select 'use secure authentication', or not; I'm not
sure how Thunderbird mistranslates SMTP AUTH - I get confused between
the way it does, and the way Outlook does. ;)
 
Oh, and Tanner already mentioned this, but SMTP != IMAP.

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