Outlook IMAPS/SMTPS issues with single client

[Apple_Eater]

Hello all,
While I am fully aware that this is most likely an outlook/client issue than a Zimbra issue, I've always found the people on this forum to be very knowledgeable and helpful, regardless of the issue.

I am having an issue with one client computer that seems entirely unable to connect to Zimbra, either via IMAPS to SMTPS. The errors on the Zimbra side read as follows:

Aug 29 22:22:20 mail postfix/smtpd[23419]: SSL_accept error from **client machine**[172.**.**.50]: -1
Aug 29 22:22:20 mail postfix/smtpd[23419]: lost connection after STARTTLS from **client machine** [172.**.**.50]

The client (Win XP SP3 w/ Outlook 2003) is unable to send or receive any emails. All other clients (some running Zimbra connector, some running IMAPS) all work perfectly, so something is amiss with this particular client.

The outlook logs provided no useful info whatsoever (after enabling debug logs).

Originally I was thinking perhaps some malicious program was trying to intercept outgoing SMTP/SMTPS connections to harvest emails, but a few scans of the machine reveal nothing, and after looking at a Wireshark log of the traffic, all appears to be in order.

Any ideas? The certs are all self-signed, but this has never been a problem before. The only notable thing that happened between the "working" and "non-working" states for this PC: the PC used to work fine, but then it became non-bootable due to extensive filesystem corruption. The harddrive was replaced, data was copied (dd), all was well, but now this issue. Could this have something to do with it? Perhaps the outlook install got corrupted in a strange way?

I'm certainly up for trying anything, as this issue has completely confused me. I'm thinking the next logical step is to reinstall outlook, as file corruption is a possible culprit. Anywhere else I should be looking?

Much appreciated!

[phoenix]

Which version of Outlook is this? Have you tried doing a repair of the installation? Are they using the correct port 587 as the Submission port? Can the user telnet to the server port(s) (587 & 993) from their machine? Have you tried importing the certificate into the browser (and/or Outlook) for this user? If you try the repair and the port change to you see the same errors in the log files?

BTW, does this user have any firewall and/or anti-virus software that may be interfering with the connection?

[Apple_Eater]

Just had a chance to interact with the end user computer some more today. I was going to visit the webmail interface to install the certs into the browser, but I noticed the user had chrome as their default. I opened IE (so I could get the certs into the actual machine store) and immediately noticed that I could not get the machine to connect to *any* HTTPS website (including webmail). Obviously something has gone wrong at a much lower level than Zimbra, Outlook, etc. I'll post back when I figure something out.