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angryiphoneuser Level 1 Level 1

I have followed the advice in to solve this but the file keeps reverting back to the original meaning I am having to re-apply this patch this every few hours at the moment.


Not sure whether this is happening when I stop and restart mail, reboot or edit some of the other postfix settings as I install roundcube - but it is extremely annoying.  Any ideas?

Solved by redshift82r on Oct 10, 2012 2:39 PM Solved

To make your settings permanent , you have three options.


The least preferred is to make the change to the config file. As you've found, these changes get nuked ever time you make a change via .


Option 2 is to find the default config file , make a copy and then make the change to the default file as well. So in your case, copy to and then edit as well as .  This way, when makes the changes , it uses a file that already has the edit.  However, this doesn't protect you from OS X server updates in the future.


The most preferred is to use the tools provided by Apple.


So the easiest and most ( but not guaranteed) future-proof method is to use serveradmin from the command line for those change that can not be made in the GUI.


Any setting you see in serveradmin can be changed by serveradmin command and will be permanent unless you make a change to the same setting via the GUI.



$ sudo serveradmin settings mail:postfix:mynetworks:_array_index:0 =

I'm pretty sure that the way to specify the range is as follows - or or


Should do the trick!




  • angryiphoneuser Level 1 Level 1

    By the way the server is 10.8.2


    I have just applied this patch for the umpteenth time and a new error from my Outlook clients:


    554 5.7.1 <external mail adddres>: relay access denied


    So now nothing works!  Has anybody seen or solved this?

  • angryiphoneuser Level 1 Level 1

    I have tried:


    - wiping my outlook configuration and reinstalling my outlook accounts

    - taking a brand new machine with Outlook 2010


    and it still doesn't work.  I now get the error that any communication with the smtp server is interrupted.  Apple suport will not help - Outlook is a Microsoft Product but the problem is definately with the server



  • Mark23 Level 3 Level 3

    The problem isn't at your client, it is at the server...

  • angryiphoneuser Level 1 Level 1

    I know that, you know that, Apple support suggests I call Microsoft!


    I can't believe that getting OSX server to talk to Outlook can be so difficult and problematic.  I have been trying to solve this all day


    There is nothing obvious in the SMTP srevr logs either

  • Mark23 Level 3 Level 3

    The Apple Mail server has four authentication methodes it can use:

    - Kerberos

    - Digest (CRAM-MD5)

    - APOP (POP only)

    - Cleartext


    Microsoft Outlook and Outlook Express can't use CRAM-MD5 authentication. The free Mozilla Thunderbird can. The problem is thus not with Apple, but with Microsoft, although I don't think calling Microsoft will help a bit.


    You can lower the Mail Server security by allowing the Cleartext authentication method, use Kerberos (better) or limit yourself to POP mail if you wish to use Microsoft products to connect to the Apple Mail server.


    Screen Shot 2012-10-10 at 17.59.24.png

  • angryiphoneuser Level 1 Level 1

    I have already doen all of those:


    Authentication is by 'Any Method' - all four options ticked in Server app and I am trying to get a POP3 connection.  Whne I test from Outlook it initally shows the POP3 connection to be okay before failing on the SMTP connection and returning:Capture.PNG


    SMTP log on the server shows:

    Oct 10 17:16:56 log[13847]: auth: Error: od(nickgray, Authentication server failed to complete the requested operation.

    Oct 10 17:16:56 log[13847]: auth: Error: od(nickgray, authentication failed for user=nickgray, method=DIGEST-MD5

    Oct 10 17:17:02 log[13847]: pop3-login: Login: user=<nickgray>, method=PLAIN, rip=, lip=, mpid=13864, TLS

    Oct 10 17:17:02 log[13847]: pop3(pid 13864 user nickgray): Disconnected: Logged out top=0/0, retr=0/0, del=0/54642, size=5472292395

  is the static IP address of the machine running the Outlook client

  • angryiphoneuser Level 1 Level 1

    Sorry that is from the mail server log


    The SMTP log has:


    Oct 10 17:17:02 postfix/postscreen[13861]: CONNECT from []:55471 to []:25

    Oct 10 17:17:02 postfix/postscreen[13861]: PASS OLD []:55471

    Oct 10 17:17:02 postfix/smtpd[13890]: connect from unknown[]

    Oct 10 17:17:02 postfix/smtpd[13890]: error: validate response: error: Authentication server failed to complete the requested operation.

    Oct 10 17:17:02 postfix/smtpd[13890]: error: validate response: authentication failed for user=nickgray (method=DIGEST-MD5)

    Oct 10 17:17:02 postfix/master[13842]: warning: process /usr/libexec/postfix/smtpd pid 13890 killed by signal 6

  • Mark23 Level 3 Level 3


  • Mark23 Level 3 Level 3

    You are likely able to change the authentication method for your outgoing mail on the client, please match that to the mechanism of your incoming mail, which seems to work fine...

  • angryiphoneuser Level 1 Level 1

    I have now explicitly set the authentiaction method instead of using "Auto" on the Outlook client and I am new back to relay access denied - one step forward = one step back


    Client shows


    SMTP log on the server shows:


    Oct 10 17:34:37 postfix/smtpd[14699]: NOQUEUE: reject: RCPT from unknown[]: 554 5.7.1 <nckgry<at>>: Relay access denied; from=<nick<at>> to=<nckgry<at>> proto=ESMTP helo=<QuadCore>

    Oct 10 17:34:38 postfix/postscreen[14698]: PASS NEW []:38754


    Mark - thank you for your help with this.  As my earlier posts suggested my patience had run out with this new Mini server.  Having invested 3 days so far to get it working with all my iOS and clients this is pretty frustrating

    Your messa

  • angryiphoneuser Level 1 Level 1

    By the way all the iOS and clients work fine - just Outlook on Mac:Office and two PC clients have this problem

  • Mark23 Level 3 Level 3

    How are your DNS settings in the server app?

  • Mark23 Level 3 Level 3

    This should be a hint

  • angryiphoneuser Level 1 Level 1

    I checked that earlier - they were imported from 10.6.8 - SLS


    primary zone: - machine,nameserver and mail exchanger


    If there was an error here I would expect the iOS and clients on the LAN not to work - but they do


    I am currently looking at permitted networks:


    On the (very reliable but now broken) SLS server I had added 'Accept SMTP relays only from these hots and networks" and added the LAN address range 192.168 etc


    This option is gone on MLS but I see in serveradmin settings mail that there is a command mail:postfix:mynetworks:_array_index:0 =  - Do you know of a way to add mail:postfix:mynetworks:_array_index:1 = 192.168etc?


    The Server app rountinely adds variables to the array but I cannot see how to do it from the command line - I can edit existing lines using serveradmin settings mail:etc but not add.  I am loathe totry and find the config file and edit as MLS seems to destroy and recreate these at every opportunity


    My best guess so far....

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