Jake Vickers wrote:
> I know this has been brought up before, but I see some fresh new shiny
> faces on the list and maybe there is some new knowledge floating out there.
> 
> I have a user that refuses to reboot Windows. He claims that it's a
> problem on my end, not his, and he should never have to reboot (but he
> also refuses to install updates since he says Windows and it's updates
> are not production stable yet - go figure).
> Anyway, he's running Office 2003, and every few days (about once a week
> to two weeks) his Outlook will hang sending messages. POP3 still works
> fine, but any and all messages hang in his outbox.  A reboot solves
> this, but he keeps insisting that it's my problem and not Outlook's. 
> This happens with plain messages, as well as ones with Word attachments.
> I do not show any SMTP errors on my end (I don't even show a connection
> in the logs to be honest) nor any other error messages. Outlook gives
> the error that the SMTP server is not responding and for him to contact
> his ISP. Other users can send emails fine using Outlook while his is
> giving this error message.  Once a message is hung, and other messages
> he sends will also hang.
> 
> Has anyone seen any type of solution to this? Other than changing to
> Thunderbird and/or Linux that is.
> I'm off to troll the KBs on MS's site and see if there are any solutions
> there.
> 

Very informative thread. Thanks to all for their input.

I recently discovered that Outlook has a timeout parameter, which can kick
in when sending large emails through a busy or low-powered server. When this
happens, the message is sent, but Outlook times out during the clamav scan,
so it doesn't realize it's been sent, and sends again and again, resulting
in the recipient receiving multiple copies until the sender eventually
removes it from Outlook's outbox. This doesn't sound like your client's
problem, but it'd be worth a check.

On a tangent to this, I've read many things about how Outlook doesn't do too
well as an IMAP client either. However, a customer had a strong need (desire
is more like it) to use IMAP with Outlook. Before switching to IMAP from
pop3, I installed dovecot on their toaster. I'm pleased to say that, while
there are a few things that Outlook does in peculiar ways with IMAP, I
haven't had any problems that haven't been able to be solved with a few
changes to Outlook's configuration. Overall, Outlook and dovecot seem to
play rather nicely together. Note, that dovecot has a configuration
parameter called "imap_client_workarounds", which allows dovecot to
circumvent various client bugs in imap implementation, including one in
Outlook that never aborts the IDLE command.

FWIW
-- 
-Eric 'shubes'

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