Topic: Urgent email problem with MS Outlook on Mac

[madadam]

Hi I'm hoping someone might be able to shed some light on this problem.

I've got a client trying to access his email from my server (SME 7.5.1) using his new Apple iMac. It works fine when using the Apple Mail client software, but as soon as he tries to use MS Outlook to retrieve POP mail it fails.

The server is set up to allow only secure POP3 connections using SSL. We have a valid wildcard SSL cert. He can actually send mail but it the receiving which is the problem.

As I said it works on Apple Mail app, not Outlook. Outlook reports "Connection to the server failed or was dropped".

Having said all that we did get it working for a short while yesterday after trying everything. Instead of a mail sever "mail.domain.com" I just put "domain.com" and it worked for a little while. Now it doesn't anymore.

Please help!

Adam

[madadam]

BTW: I have been able to reproduce this on my office Mac using an older version of MS Office which had Entourage (predecessor to Outlook on the Mac).

Adam

[madadam]

Found these errors in the POP3S log file:

2010-12-16 19:37:17.546885500 Couldn't verify MAC or pad of record data
2010-12-16 19:37:17.546969500 sslio[8587]: fatal: ssl decode error: bad record mac

These in itself didn't help particularly but I started looking in other directions as I saw that Entourage/Outlook was actually making a connection but failing once it began the transaction.

The client had his email software set to leave email on the server for 30 days. However his MailDir/cur folder contained email files close to two months old. After using a test account with over 2000 spam emails it too failed with Entourage/Outlook. But delete the majority of those emails and it worked fine.

So went to the client's account, backed up his /cur folder and then deleted anything over 30 days and lo and behold it worked without problem.

So, problem fixed. But what was really the problem? Any theories?

Cheers,
Adam

[CharlieBrady]

But what was really the problem? Any theories?

MS Outlook.

[madadam]

MS Outlook.

Agreed. Unfortunately the majority of my clients all run some version of Outlook.

I did subtly try to encourage my client to use Apple Mail as we've NEVER experienced any compatibility problems with that and the POP/IMAP/SMTP implementation on SME Server.

Cheers!
Adam

[mmccarn]

Post withdrawn - I had not read the original post completely...

[CharlieBrady]

Found these errors in the POP3S log file:

2010-12-16 19:37:17.546885500 Couldn't verify MAC or pad of record data
2010-12-16 19:37:17.546969500 sslio[8587]: fatal: ssl decode error: bad record mac

I would guess this would be due to Outlook sending some plain text down what should be an SSL (encrypted) socket connection.

[madadam]

I would guess this would be due to Outlook sending some plain text down what should be an SSL (encrypted) socket connection.

Possibly. It seems Outlook is getting a little confused when it finds there is a lot of emails to download and yes you might be right it might accidentally send some plain text.

Cheers,

adam