Eric Shubert wrote:


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.

Some very good ideas and hints in there. I'm leaning toward a script to run nightly to restart his Outlook to be honest. How did dovecot go? I've been considering benching it here, but to be honest I don't want to have to do a lot of work arounds to get Outlook working. I've got 100+ clients on one server all using Outlook and it would be a nightmare to try and wrestle that alligator. Some of them even change laptops every other month when a new model comes out, so it would be a demonstration in pain for this one.
What were some of the other issues?

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