9 Replies Latest reply: May 9, 2013 7:49 AM by Alfista_SK
Alfista_SK Level 1 Level 1 (0 points)

Hi,

 

I hope that anybody can help me. I have Mountan Lion with latest OS X Server app and from installing I have problems to send mail from MS Outlook. I have Authentication on Automatic and I have removed "reject_non_fqdn_helo_hostname" from main.cf file but still can't send the messages. On Mac or iOS is it working.

Please can anybody help me and tell what I need to set that it works?


OS X Server
  • MrHoffman Level 6 Level 6 (13,005 points)

    What are the associated messages in the mail server's SMTP and related logs?

  • Alfista_SK Level 1 Level 1 (0 points)

    Loging on POP and IMAP is OK, only sneding mail fails.

    This was in SMTP Logu after automatic Outlook settings:

     

    May  6 16:26:22 server1.prostudio.sk postfix/postscreen[3595]: CONNECT from [77.247.225.215]:49240 to [100.0.0.251]:25

    May  6 16:26:22 server1.prostudio.sk postfix/postscreen[3595]: PASS OLD [77.247.225.215]:49240

    May  6 16:26:22 server1.prostudio.sk postfix/postscreen[3595]: CONNECT from [77.247.225.215]:49239 to [100.0.0.251]:25

    May  6 16:26:22 server1.prostudio.sk postfix/postscreen[3595]: PASS OLD [77.247.225.215]:49239

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: connect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: lost connection after UNKNOWN from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: disconnect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: connect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: connect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: lost connection after UNKNOWN from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: disconnect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3600]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3600]: connect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: lost connection after UNKNOWN from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: disconnect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: connect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3594]: connect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/postscreen[3595]: CONNECT from [77.247.225.215]:49246 to [100.0.0.251]:25

    May  6 16:26:22 server1.prostudio.sk postfix/postscreen[3595]: PASS OLD [77.247.225.215]:49246

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: lost connection after UNKNOWN from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: disconnect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3597]: connect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/postscreen[3595]: CONNECT from [77.247.225.215]:49248 to [100.0.0.251]:25

    May  6 16:26:22 server1.prostudio.sk postfix/postscreen[3595]: PASS OLD [77.247.225.215]:49248

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3603]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3603]: connect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3600]: lost connection after STARTTLS from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3600]: disconnect from unknown[77.247.225.215]

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3600]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:22 server1.prostudio.sk postfix/smtpd[3600]: connect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3594]: lost connection after STARTTLS from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3594]: disconnect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3597]: lost connection after STARTTLS from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3603]: lost connection after STARTTLS from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3597]: disconnect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3603]: disconnect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/postscreen[3595]: CONNECT from [77.247.225.215]:49254 to [100.0.0.251]:25

    May  6 16:26:23 server1.prostudio.sk postfix/postscreen[3595]: PASS OLD [77.247.225.215]:49254

    May  6 16:26:23 server1.prostudio.sk postfix/postscreen[3595]: CONNECT from [77.247.225.215]:49256 to [100.0.0.251]:25

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3600]: lost connection after EHLO from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/postscreen[3595]: PASS OLD [77.247.225.215]:49256

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3600]: disconnect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3594]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3594]: connect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3603]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3597]: warning: hostname suska.router-3.tvbox.sk does not resolve to address 77.247.225.215

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3603]: connect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3597]: connect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3594]: lost connection after EHLO from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3594]: disconnect from unknown[77.247.225.215]

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3597]: error: validate response: error: Authentication server failed to complete the requested operation.

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3597]: error: validate response: authentication failed for user=nora (method=DIGEST-MD5)

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3603]: error: validate response: error: Authentication server failed to complete the requested operation.

    May  6 16:26:23 server1.prostudio.sk postfix/smtpd[3603]: error: validate response: authentication failed for user=nora (method=DIGEST-MD5)

    May  6 16:26:24 server1.prostudio.sk postfix/master[2121]: warning: process /usr/libexec/postfix/smtpd pid 3603 killed by signal 6

    May  6 16:26:24 server1.prostudio.sk postfix/master[2121]: warning: process /usr/libexec/postfix/smtpd pid 3597 killed by signal 6

     

    and if I set all manualy, all ports like on macs witch works in SMTP Logs is nothing and in Outlook is:

    Your server does not support the connection encryption type you have specified. Try changing the encryption method.

     

    I know that WIn doesn't support Cram-MD5 so I have selected all methods to authenticate.

  • MrHoffman Level 6 Level 6 (13,005 points)

    The mail server DNS is incorrect; the forward and reverse translations don't match the MX record for the domain.  That'll cause some mail intended to be sent from remote servers to yours to be dropped on the floor and not sent, and it'll cause mail sent to remote servers also dropped.

     

    As a test, configure the client for plain text via SSL via the submission port.  (As part of this, don't allow your mail clients to chat with port 25 directly, and make sure SSL/TLS is enabled.)

  • Alfista_SK Level 1 Level 1 (0 points)

    OK I will test it, but when I had 10.6 system all was OK, but only when I change to 10.8 are now this problems. And I know that I have all DNS records configured properly. And I have closed port 25 and SSL is active.

  • Alfista_SK Level 1 Level 1 (0 points)

    Witch is the submission port? I have confured 993, 995 and 465, 587.

     

    And the client allways tell me thet I have wrong ancryption ... I have seted all. All macs clients use cram-md5 but I know that win clients don't know it, so I have seted all methods ... isn't possible that I need to reconfigute that? But I don't know how ...

  • MrHoffman Level 6 Level 6 (13,005 points)

    OS X Server 10.6 didn't care about local DNS quite as much as do later releases of OS X.

     

    DNS is a fundamental part of network security, and of SSL/TLS network encryption.

     

    Beyond some basics, your local mail server doesn't really care about DNS, either.  It is the other mail servers on the network that care about your DNS, as you do not want your mail server to be indistinguishable from a spam engine.  Other mail servers will evaluate your DNS, and will determine you're a spam engine, and will not bother sending you mail, or will simply drop mail your server has sent out.

     

    993 and 995 are IMAP SSL/TLS and POP SSL/TLS ports; these ports are used to read mail.

     

    Mail servers use TCP 25 to communicate server-to-server, and sometimes client-to-server.

     

    What's variously considered good networking practice has outbound TCP port 25 traffic blocked, as that suppresses the ability of spam engines and unauthorized SMTP servers from sending out messages.  This is one of the reasons why having clients communicate with servers via port 25 isn't reliable.  There are other reasons.

     

    The SMTP submission ports are TCP 587 and the legacy submission port is TCP 465.

     

    Apple has published a list of IP ports used by iOS and OS X applications (TS1629).

     

    If you're getting an encryption error rather than a credentials error, then there's either a low-level error with your SSL/TLS implementation, or a very fundamental incompatibility. 

     

    If you're getting credentials or authentication errors and not encryption errors, then you will want to look at the documentation for the particular version of the mail client(s) your folks are using and also at your mail server logs to determine what password mechanism is being used (and rejected) by the particular clients, and then use Server Admin.app or Server.app to configure the authentication available on the mail server.

     

    As mentioned in an earlier reply, ensure your server is configured to permit SSL/TLS on the submission ports and also SSL/TLS on POP and/or IMAP ports, then try enabling plain-text authentication.  I generally don't allow any non-SSL/TLS connections, and typical practices with mail servers now often deprecate unencrypted client-server connections.

     

    The exact text of the diagnostics you're getting here can be important, too.  What sort of encryption or credentials diagnostic is being displayed here.

  • Alfista_SK Level 1 Level 1 (0 points)

    The MS Outlook writes that he has problem with the wrong encryption type.

    I have in Server.app seted SSL for IMAP, POP and SMTP and in authentication are set all, Clear-text too (is it the same like the Plai-Text?)

     

    Tell me all what I should check and send it to you that we can find the problem.

     

    PS.: I have instaled Thunderbird on that PC and that can conect to the mail server without any problems like all apples clients.

  • MrHoffman Level 6 Level 6 (13,005 points)

    Confusingly, Microsoft Outlook and Microsoft Outlook Express are different products, and there are different versions of each.  Can you post details of which client and version you have here?

     

    I do not have recent experience with Microsoft Outlook or Outlook Express products, and do not have any Microsoft Outlook or Outlook Express clients connected to the local OS X Server to test with, so I'm not going to be able to provide assistance there. 

     

    Consider asking some Microsoft folks how to get that client to communicate with a generic Unix or Linux mail server that's running Postfix & Dovecot; these are common mail servers on the 'net, and somebody that knows Microsoft Outlook may (will?) know some details of connecting to these mail servers.

     

    As for the "encryption" error, please do not paraphrase the wording of the error message(s) or diagnostics you're seeing.  The exact text of the diagnostic often matters a great deal for these sorts of questions.

     

    Microsoft Outlook is a mail client primarily intended for use with Microsoft Exchange Server, and not a mail client that's more typically used with other mail servers.  AFAIK, it can work, but at least the older versions of Microsoft Outlook had all sorts of issues with non-Microsoft mail servers.

     

    Microsoft Outlook Express is a Microsoft mail client that is more commonly used with mixed-network and non-Microsoft configurations; with Unix and Linux (and OS X Server) mail servers.  Here is a write-up on getting Outlook Express working with PostfixHere are Microsoft's general Outlook Express instructionsHere are some related instructions for both Outlook and Outlook Express.

     

    Again, I have no Microsoft Outlook or Microsoft Outlook Express clients available to test with, and would suggest trying a Microsoft forum for this question — while they probably won't know from OS X Server here, they likely do have experience with connecting to Postfix and Dovecot servers, which are the packages used on OS X Server.

  • Alfista_SK Level 1 Level 1 (0 points)

    Thanks, but the problem isn't in how the outlook is set up ( i have set it up corectly, manualy), but i let there the thunderbird and it's working.

     

    I have a another question if I can.

     

    1. I have activated the calendar and foud that thera to calendar account (local and network) and one is write that it can conect to the mail server with the plai-text. I thing it is the local one. Can I delete this account?

    2. Have you set in Apples mail server the SASL Authentication?

    3. Have you installed Roudcubemail or other one web portal for mac's mail server? Witch one is good and it's possible there some automations for mails? Like Auto making JunkMail folder for all clients and moving there all junkmail.

     

    Thanks.