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Date:      Thu, 31 Jul 2008 09:07:41 +0200
From:      Jonathan McKeown <jonathan@hst.org.za>
To:        freebsd-questions@freebsd.org
Cc:        Andrew Falanga <af300wsm@gmail.com>
Subject:   Re: Having some problems with a FreeBSD mail server (SMTP)
Message-ID:  <200807310907.41947.jonathan@hst.org.za>
In-Reply-To: <200807301835.17740.af300wsm@gmail.com>
References:  <200807301835.17740.af300wsm@gmail.com>

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On Thursday 31 July 2008 02:35, Andrew Falanga wrote:
> Hi,
>
> I run a mail server for my church.  Today I was called that folks are able
> to receive, but not send their mail.  They are all currently configured for
> POP3 (I use dovecot).
>
> At home I tried to send mail to two different e-mail accounts of mine using
> the church e-mail server and was successful.  I used KMail for this.
>
> As I look through /var/log/maillog I do not even see
> authid=<their_user_ids> in the mail log (I'm using TLS with sendmail).  One
> of the pastor's told me the error he's seeing is "timeout."  They are using
> Outlook, I'm not sure of the version.  What problems do people here usually
> encounter with Outlook mail clients and their SMTP servers?
>
> At this point, I'd just like to have some leads.  Any ideas what might be
> keeping them from sending?  They can all log in and receive e-mail POP3.

I'm using TLS and SMTP AUTH with sendmail - all my users are on Microsoft 
Outlook 2003 (bar one on Thunderbird and me on KMail).

Outlook didn't do TLS properly until Outlook 2003 Service Pack 2 or 3 - the 
symptom was repeated timeouts on trying to send mail. Even after upgrading 
all the users to SP3, we still occasionally have a similar problem. A user 
will try to send mail, the TLS negotiation will time out, and from that point 
on mail will just accumulate in the outbox. Outlook has to be closed down and 
restarted before it will correctly try the TLS connection again.

We also encountered another issue, which may or may not be related to using a 
Windows AD domain, which was that Outlook will reuse message-IDs - generally 
by copying the message-ID of an original message and using it as the 
message-ID for the reply. This one bit me twice: once when a user (quite 
correctly) complained that she was losing email. On investigation, it turned 
out that her manager had sent three or four different messages in reply to 
messages of hers, and Cyrus imapd had binned them all as duplicates based on 
the copied message-ID. I had to switch off duplicate suppression in imapd.

The second time - which I haven't found a solution for - is in Mailman. The 
HTML pages for archives are built using the assumption that message-IDs are 
unique: the result is that when two messages have the same message-ID, only 
one of them will appear in the archive. (Which one is random, so I suspect 
Mailman is using the message ID as a hash key internally).

I get the feeling that Microsoft pay lip-service to the standards, but don't 
really carry out proper testing against anything other than Microsoft 
Exchange (after all, why would you use anything else?!). Outlook doesn't 
support IMAP well.

Worst, from my point of view, I have regular complaints that people using POP3 
are losing email. By using telemetry in Cyrus imapd, I've been able to 
establish that there's no problem server-side: Outlook is downloading the 
mail, and then throwing it away. Try telling a user that Microsoft stuffed 
up, though.

(Sorry - this turned into an Outlook rant. I hope you find some benefit in the 
early paragraphs, before I started frothing at the mouth and throwing my 
toys).

Jonathan



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