SMTP authentication not working with Microsoft Entourage

[thewolf]

Hi,

We're running Plesk 8.1.1 on Red Hat Enteprise Linux 4.

When we try to send a message through the Plesk server with Microsoft Entourage 2004 using SMTP authentication, it fails with the following error message:

Authentication failed because Entourage doesn't support any of the available authentication methods.

Any ideas on what's the issue and how to fix it?

Thanks.

 

[webfeatus]

NTLM version 1 authentication:
Is it possible to set the server to use an auth/challenge version that mac entourage and all other email clients can accommodate?

NOTE:
This issue does not exist with cPanel.

FACT:
A very annoying and unfriendly situation.

QUESTION:
What can be done about this?

 

[reliablepenguin]

This problem is caused by Qmail on recent versions of plesk failing to include an AUTH statement in response to EHLO commands.

From older servers:

> telnet rs04.reliablepenguin.com 25
Trying 72.32.68.171...
Connected to rs04.reliablepenguin.com.
Escape character is '^]'.
220 rs04.reliablepenguin.com ESMTP
ehlo
250-rs04.reliablepenguin.com
250-AUTH=LOGIN CRAM-MD5 PLAIN
250-AUTH LOGIN CRAM-MD5 PLAIN
250-STARTTLS
250-PIPELINING
250 8BITMIME

From newer servers:

> telnet localhost 25
Trying 127.0.0.1...
Connected to localhost.
Escape character is '^]'.
220 xxx.mydomain.com ESMTP
ehlo
250-xxx.mydomains.com
250-STARTTLS
250-PIPELINING
250 8BITMIME

The lack of the AUTH lines is causing some mail clients to not attempt SMTP AUTH because they think the server does not support it.

Don't have the solution yet to this problem. Has anybody solved it already?

 

[webfeatus]

My tech knowledge is very limited.
I discussed the issue with my server administrators.
They opened the original qmail on port 26
I assume the version which is not modified by Plesk.
Obviously this has some limitations re: spam services, etc.
However, so far, if I tell a mac entourage client to use smtp port 26 - the workaround seems to be successful.

This may assist.

I would certainly appreciate any further feedback on this issue. It is very difficult to find anyone who agrees with me that this is a Plesk issue. Most people, including Plesk support, simply point to the Microsoft documentation which indicates an issue with Entourage.