From owner-freebsd-questions@FreeBSD.ORG Thu Jul 31 07:07:02 2008 Return-Path: Delivered-To: freebsd-questions@freebsd.org Received: from mx1.freebsd.org (mx1.freebsd.org [IPv6:2001:4f8:fff6::34]) by hub.freebsd.org (Postfix) with ESMTP id EAB901065674 for ; Thu, 31 Jul 2008 07:07:02 +0000 (UTC) (envelope-from jonathan@hst.org.za) Received: from hermes.hst.org.za (onix.hst.org.za [209.203.2.133]) by mx1.freebsd.org (Postfix) with ESMTP id 25E128FC14 for ; Thu, 31 Jul 2008 07:07:00 +0000 (UTC) (envelope-from jonathan@hst.org.za) Received: from sysadmin.hst.org.za (sysadmin.int.dbn.hst.org.za [10.1.1.20]) (authenticated bits=0) by hermes.hst.org.za (8.13.8/8.13.8) with ESMTP id m6V72n7C065275 (version=TLSv1/SSLv3 cipher=RC4-MD5 bits=128 verify=NO); Thu, 31 Jul 2008 09:02:49 +0200 (SAST) (envelope-from jonathan@hst.org.za) From: Jonathan McKeown Organization: Health Systems Trust To: freebsd-questions@freebsd.org Date: Thu, 31 Jul 2008 09:07:41 +0200 User-Agent: KMail/1.7.2 References: <200807301835.17740.af300wsm@gmail.com> In-Reply-To: <200807301835.17740.af300wsm@gmail.com> MIME-Version: 1.0 Content-Type: text/plain; charset="iso-8859-1" Content-Transfer-Encoding: 7bit Content-Disposition: inline Message-Id: <200807310907.41947.jonathan@hst.org.za> X-Spam-Score: -4.371 () ALL_TRUSTED,AWL,BAYES_00 X-Scanned-By: MIMEDefang 2.61 on 209.203.2.133 Cc: Andrew Falanga Subject: Re: Having some problems with a FreeBSD mail server (SMTP) X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.5 Precedence: list List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Thu, 31 Jul 2008 07:07:03 -0000 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= 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