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SMTP authentication not working with Microsoft Entourage

Discussion in 'Plesk for Linux - 8.x and Older' started by thewolf, Sep 24, 2007.

  1. thewolf

    thewolf Regular Pleskian

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

    Thanks.
     
  2. webfeatus

    webfeatus Guest

    0
     
    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?
     
  3. reliablepenguin

    reliablepenguin New Pleskian

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    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?
     
  4. webfeatus

    webfeatus Guest

    0
     
    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.
     
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