Mail Authentication fails in OSX on port 465

I've been stumbling upon this for a few days now. I use OSX Mail and somehow I just can't configure it to work with my Debian Squeeze with ISPConfig 3.

Problem:
ISP blocks port 25
So I try to connect through 465
And yes I want a secure connection...

What I've done:
Decomment in /etc/postfix/master.cf

Code:

smtps     inet  n       -       -       -       -       smtpd

Restart postfix

Enable firewall port 465

Checked telnet, outcome on port 465:

Code:

Escape character is '^]'.
220 vps.domain.com ESMTP Postfix (Debian/GNU)
ehlo localhost
250-vps.domain.com
250-PIPELINING
250-SIZE
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH PLAIN LOGIN
250-AUTH=PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN

Seems okay right? But OSX mail keeps complaining it cannot reach the server. Mail retrieval is possible. In both cases I use mail.domain.com (IMAP and SMTP.

So different operating system then... Ubuntu 10.10 mail client (Evolution). It works but only if I use TLS.

Back to OSX.. nope.. doesn't work. I've already specified to use port 465 on Advanced settings. But just can't figure it out. I've even done a full reboot of the server... enabled/disables ssh, but no luck so far. Pleeezz help , how do I configure my server OSX Mail also works.

 

Are there any errors in your mail log (in the /var/log/ directory)?

 

Hi Falko, thank u for replying. I did find these messages today in mail.log:

Code:

Apr 12 17:57:35 vps postfix/smtpd[32323]: connect from isp.domain.com[xxx.xxx.xxx.xxx]
Apr 12 18:02:35 vps postfix/smtpd[32323]: lost connection after UNKNOWN from isp.domain.com[xxx.xxx.xxx.xxx]
Apr 12 18:02:35 vps postfix/smtpd[32323]: disconnect from isp.domain.com[xxx.xxx.xxx.xxx]

As follows from the timestamp the second and third message appear only after OSX Mail end because of a time-out. The telnet connect and ehlo localhost and quit appear normally.

In the working Ubuntu the following appears:

Code:

Apr 12 18:26:13 VPS postfix/smtpd[596]: connect from isp.domain.com[xxx.xxx.xxx.xxx]
Apr 12 18:26:14 VPS postfix/smtpd[596]: 38A839C511: client=isp.domain.com[xxx.xxx.xxx.xxx], sasl_method=PLAIN, [email protected]
Apr 12 18:26:14 VPS postfix/cleanup[599]: 38A839C511: message-id=<[email protected]>
Apr 12 18:26:14 VPS postfix/qmgr[2023]: 38A839C511: from=<[email protected]>, size=928, nrcpt=1 (queue active)
Apr 12 18:26:15 VPS postfix/smtpd[596]: disconnect from isp.domain.com[xxx.xxx.xxx.xxx]
Apr 12 18:26:15 VPS postfix/smtp[601]: 38A839C511: to=<[email protected]>, relay=ASPMX.L.GOOGLE.COM[xxx.xxx.xxx.xxx]:25, delay=1.6, delays=0.25/0.01/0.13/1.2, dsn=2.0.0, status=sent (250 2.0.0 OK 1302632774 p50si16587853eei.98)
Apr 12 18:26:15 vps1042 postfix/qmgr[2023]: 38A839C511: removed

And what I did was disable the virusscanner (before using mail) by editing main.cf and commenting:

Code:

#content_filter = amavis:[127.0.0.1]:10024
#receive_override_options = no_address_mappings

And in master.cf:

Code:

#amavis unix - - - - 2 smtp
#        -o smtp_data_done_timeout=1200
#        -o smtp_send_xforward_command=yes

#127.0.0.1:10025 inet n - - - - smtpd
#        -o content_filter=
#        -o local_recipient_maps=
#        -o relay_recipient_maps=
#        -o smtpd_restriction_classes=
#        -o smtpd_client_restrictions=
#        -o smtpd_helo_restrictions=
#        -o smtpd_sender_restrictions=
#        -o smtpd_recipient_restrictions=permit_mynetworks,reject
#        -o mynetworks=127.0.0.0/8
#        -o strict_rfc821_envelopes=yes
#        -o receive_override_options=no_unknown_recipient_checks,no_header_body_checks
#        -o smtpd_bind_address=127.0.0.1

But I don´t think that´s the problem since everything works in Ubuntu right?

And last but not least an error appeared while figuring this error out when connecting to the server for incoming mail (pop/imap), which was solved by installing gamin instead of fam.

 

Tried it with a ubuntu 10.04/ISP3 setup, but this results in the same problem. It's gotta be something with OSX Mail that is not working very well. But I just can't find out what the problem is.

Isn't it strange a connection pops up, but nothing seems to happen while everything seems configured allright?

Any thoughts on this are appreciated!

 

Hm, I have no idea... Unfortunately I don't have a Mac to test.

 

Ok the solution was not that hard... I also had to uncomment the following lines in master.cf for OSX Mail to work.

Code:

smtps     inet  n       -       n       -       -       smtpd
  -o smtpd_tls_wrappermode=yes
  -o smtpd_sasl_auth_enable=yes
  -o smtpd_client_restrictions=permit_sasl_authenticated,reject

Still, I haven't got a clue why it did work in Ubuntu and not in OSX Mail. So if someone has any ideas about this, share them