Lindsay Haisley writes:

On Fri, 2008-12-05 at 22:18 -0600, Lindsay Haisley wrote:
On Fri, 2008-12-05 at 18:35 -0500, Sam Varshavchik wrote:
> Lindsay Haisley writes:
> > > I have a courier installation running courier 0.60.0 which delivers
> > _most_ email from the system and for remote clients using it for
> > relaying with no problem.  Occasionally, however, something like the
> > following happens:
> > > > Dec 5 09:02:07 shakti courieresmtp: id=000000000021DBA1.000000004939426F.00003979,from=<[EMAIL PROTECTED]>,addr=<[EMAIL PROTECTED]>: No such file or directory
> > Dec  5 09:02:07 shakti courieresmtp: 
id=000000000021DBA1.000000004939426F.00003979,from=<[EMAIL PROTECTED]>,addr=<[EMAIL 
PROTECTED]>,status: deferred
> > > > This seems to be associated with particular (remote) addresses, since
> > the emails are queued for retry and fail repeatedly.  Other (most)
> > addresses have no such problems and the emails are delivered normally.
> > If I telnet to port 25 on the server and send an email manually I don't
> > see a problem in the SMTP dialog (I get a "250 Ok" after the data
> > segment followed by the message ID), but if I check the mail log I see
> > the same "No such file or directory" message.  Is this something that's
> > coming from the remote end without a proper error code, or something
> > that's being generated by courier?
> > The error message is generated by Courier, but it's not clear why. Perhaps > looking at any preceding messages for this recipient will be helpful.

I went through a bunch of log entries on messages that failed with this
message and compared them with successful deliveries.  One thing thread
that I've noticed so far is that when I contact the MX servers
associated with the failed addresses they all advertise TLS and STARTTLS
whereas those that are successful don't do so.  Courier may be failing
to find one of it's TLS/SSL components.  Maybe I can disable client-side
TLS for these servers and see if that puts a band-aid on the problem.

OK, Sam,  I set ESMTP_USE_STARTTLS=0 in /etc/courier/courierd and the
problem goes away, however it appears that all of the files and
directories related to TLS and STARTTLS specified in the various config
files in /etc/courier are there, so courieresmtp is looking for
_something_, somewhere in the local filesystem, and not finding it.
What might this be?

Well, first you need to determine whether it is indeed some configuration file that's missing. If you can succesfully deliver mail to some hosts with SSL, but not others, that still points to some host-specific issue.

But if you do indeed fail to deliver using SSL to any host due to a missing configuration file, it may very well be that the setting is completely missing from your configuration file.

But for sending mail with SSL the only setting that's required is TLS_TRUSTCERTS which should point to your root CA list. If you're using a client certificate (unlikely) you'll also need to set TLS_CERTFILE or TLS_DHCERTFILE. Note that for sending mail, the TLS configuration settings are the one that are set in the courierd configuration file, not any of the *ssl configuration files.

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