Re: Postfix + AUTH/TLS + Outlook/OE problem

On Thu, Aug 17, 2006 at 03:52:02PM -0500, Adrian Gonzalez wrote:
I'm seeing some very strange behavior with Outlook 2003 and Outlook Express
trying to send mail using TLS/SMTP Auth with Postfix 2.3 and FreeBSD
6.1-STABLE

It seems like Outlook/OE don't like the SSL handshake for some reason.
They connect to the server, issue STARTTLS, and disconnect during the
handshake, giving an "Error Number: 0x800CCC0B". I've tried both STARTTLS
and using 'wrapper mode' on port 465 with the same results. Other clients
like Thunderbird are able to send just fine using the same server
w/STARTTLS, so I'm assuming it's not a configuration/authentication issue.

I thought it could be related to the chained SSL certificate we're using
(GoDaddy), but the results were the same with a self-signed cert.

I also tried updating OpenSSL to the latest 'stable' release (0.9.7j), same
results.

I've been banging my head against the wall with this one

You don't seem to have considered the possibility that Microsoft software is
simply broken. When another client connects without any problem at all, this
would seem to be a pretty fair conclusion. You could always go and ask
Microsoft what "Error 0x800CCC0B" means though.

To make matters even stranger, in Outlook Express, when you create the
message and click send, you get the error message and the email stays in
the outbox. After that if you do a Send/Receive, OE is able to negotiate
TLS properly and sends the message just fine.

So the client fails first time, and works correctly the second. Sounds like
a client bug to me.
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