7 Replies Latest reply: Jul 16, 2013 12:10 PM by Jon P
JT Harvey Jr. Level 2 Level 2

I recently upgraded to Mountain Lion form lion and am experiencing a MAIL issue (FAILURE)


I beleive I need to restablish or open ports on my router but the common ones don't seem to be doing the trick for users using Outlook. I have the Apple document that talks about the most common used ports but my Netgear router limits me to 20 so I need to narrow down the selction a bit.


Any assistance would be appreciated.


Right now, these are the ports being forwarded: (and yes, many can be eliminated)


#Service NameExternal Start PortExternal End PortInternal Start PortInternal End PortInternal IP address
14email rules8089808980898089192.168.15.101
  • MplsEE08 Level 1 Level 1

    The five ports you have open for mail should be just fine. This article might help you.



  • JT Harvey Jr. Level 2 Level 2

    Thank you Taylor for your response! The article you are speaking of is the article I referenced and is a great reference.


    Like you, I keep thinking that I have set everything correctly to allow a Windows Outlook client to authenticate and send/receive mail from the Mountain Lion server, but it just is working since I upgraded to Mountain Lion.



    The error I keep getting is a 504 5. 5. 2 <EI052014L33R1> error.


    Any additional assistance is greatly appreciated.


    Thank you!

  • MplsEE08 Level 1 Level 1

    Are you able to access accounts from OS X Mail or iOS Mail apps?

  • UptimeJeff Level 4 Level 4

    Regarding Outlook. Can it receive, send or neither?


    If the problem is sending, two things to look at.


    - You are configured for port 587 which is TLS.

    In outlook, select TLS (not SSL)

    I prefer to enable port 465 which is SSL, this plays well with outlook.

    To do so, you need to edit


    Look for these lines

    #465      inet  n       -       n       -       -       smtpd
    #  -o smtpd_tls_wrappermode=yes
    #  -o smtpd_sasl_auth_enable=yes
    #  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
    #  -o milter_macro_daemon_name=ORIGINATING

    Uncomment them all. DO NOT remove the space before the -o (its required)

    Then issue

    sudo postfix reload


    Make sure 465 is open in your router

    Retry Outlook


    587 = TLS

    465 = SSL



    - Look at your smtp logs, do you see helo errors when you try to send from Outlook?

    If so, do this (good idea to do this for ANY installation)




    smtpd_helo_restrictions = reject_non_fqdn_helo_hostname reject_invalid_helo_hostname

    Change to:    

    smtpd_helo_restrictions = permit_sasl_authenticated permit_mynetworkseject_non_fqdn_helo_hostname reject_invalid_helo_hostname

    Then issue    

    sudo postfix reload



    If this doesn't solve the issue.

    Please post whether this is a receiving or sending problem.

    If receiving, post output of mailaccess.log(imap) log when you attempt to pickup mail

    If sending, post output of your mail.log(smtp) when you try to send.



  • JT Harvey Jr. Level 2 Level 2

    Thank  you!


    This still did NOT resolve the issue. I also am noticing that I am unable to use the "messaging" service, new to 10.8 while working behind my router.


    I am all for security but this is getting a bot tiresome.

  • UptimeJeff Level 4 Level 4

    regarding mail (messaging is another thread)


    As requested earlier. Please post relevant lines from mail.log and mailaccess.log

    Are you having trouble sendin, receiving or both?


    These should yield clues.

  • Jon P Level 1 Level 1
    Mac OS X

    Hi JT,


    I suppose you already know it's best not to open ports that you don't need. A TCPdump might help you to see what's being called on...




    Also you said router so I assume you are connecting to a WAN using a common Broadband provider. Don't rule out their making changes on their end so you can't send. It does happen, not likely but it does happen. They could have made some changes during the time you were adding your upgrade OS.


    You might also try little snitch to assist in gleaning some additional information from the connections your computer tries to make. I use it often when trying to sort out what's making network calls.


    Good luck.