[SWLUG] SMTP Problems

Fri Jan 28 09:36:04 UTC 2011

Hi folks,

I am having (and always have had) a problem with my SMTP setup. Ever
since I have been running my own mail server I cannot seem to quite get
it set up right so that I can send mail from a _remote_ device. Sending
works fine 'from the server' i.e. if I ssh in and use mutt, or if I use
Roundcube installed on my server through a browser.

But I cannot get the settings quite right when trying to set up a remote
client, e.g. I am trying to use Maildroid and K9 on my Android phone. I
can access my mail fine, read all the different imap folders, but I
cannot send. 

During the set up of the account on the client, when entering SMTP
details, I am not 100% sure what I should be entering based on how I set
my system up. I set my system up using this guide >
http://www.howtoforge.com/perfect-server-ubuntu8.04-lts-p5

...so i think I should be able to use SMTP with TLS (although tbh I am a
little uncertain to what everything means).

When I try to set up the account, I get an authentication error for
SMTP.

This is what /var/log/mail.log says when I try to set up my account on
the remote device (and it tries to connect) using the following settings:

Incoming IMAP server using TLS/SSL on port 993
Outgoing SMTP server NOT using TLS/SSL on port 25

-----------------------
Jan 28 09:29:48 jcrdevelopments imapd-ssl: Connection,
ip=[::ffff:89.192.0.16]
Jan 28 09:29:48 jcrdevelopments imapd-ssl: LOGIN, user=jonr,
ip=[::ffff:89.192.0.16], port=[32512], protocol=IMAP
Jan 28 09:29:49 jcrdevelopments imapd-ssl: LOGOUT, user=jonr,
ip=[::ffff:89.192.0.16], headers=0, body=0, rcvd=26, sent=243, time=1,
starttls=1
Jan 28 09:29:54 jcrdevelopments postfix/smtpd[14282]: connect from
unknown[109.181.126.59]
Jan 28 09:29:54 jcrdevelopments postfix/smtpd[14285]: connect from
unknown[109.181.126.59]
Jan 28 09:29:54 jcrdevelopments postfix/smtpd[14285]: setting up TLS
connection from unknown[109.181.126.59]
Jan 28 09:29:55 jcrdevelopments postfix/smtpd[14282]: lost connection
after UNKNOWN from unknown[109.181.126.59]
Jan 28 09:29:55 jcrdevelopments postfix/smtpd[14282]: disconnect from
unknown[109.181.126.59]
Jan 28 09:29:55 jcrdevelopments postfix/smtpd[14285]: Anonymous TLS
connection established from unknown[109.181.126.59]: TLSv1 with cipher
DHE-RSA-AES256-SHA (256/256 bits)
Jan 28 09:29:56 jcrdevelopments postfix/smtpd[14285]: warning: SASL
authentication failure: cannot connect to saslauthd server: No such file
or directory
Jan 28 09:29:56 jcrdevelopments postfix/smtpd[14285]: warning:
unknown[109.181.126.59]: SASL LOGIN authentication failed: generic
failure
Jan 28 09:29:56 jcrdevelopments postfix/smtpd[14285]: lost connection
after AUTH from unknown[109.181.126.59]
Jan 28 09:29:56 jcrdevelopments postfix/smtpd[14285]: disconnect from
unknown[109.181.126.59]
Jan 28 09:29:56 jcrdevelopments postfix/smtpd[14282]: connect from
unknown[109.181.126.59]
Jan 28 09:29:57 jcrdevelopments postfix/smtpd[14282]: warning: SASL
authentication failure: cannot connect to saslauthd server: No such file
or directory
Jan 28 09:29:57 jcrdevelopments postfix/smtpd[14282]: warning:
unknown[109.181.126.59]: SASL LOGIN authentication failed: generic
failure
Jan 28 09:29:57 jcrdevelopments postfix/smtpd[14282]: lost connection
after AUTH from unknown[109.181.126.59]
Jan 28 09:29:57 jcrdevelopments postfix/smtpd[14282]: disconnect from
unknown[109.181.126.59]
---------------------

And if I switch outgoing SMTP server to use TLS/SSL on port 587:

--------------------------
Jan 28 09:32:30 jcrdevelopments imapd-ssl: Connection,
ip=[::ffff:89.192.0.16]
Jan 28 09:32:30 jcrdevelopments imapd-ssl: LOGIN, user=jonr,
ip=[::ffff:89.192.0.16], port=[37134], protocol=IMAP
Jan 28 09:32:31 jcrdevelopments imapd-ssl: LOGOUT, user=jonr,
ip=[::ffff:89.192.0.16], headers=0, body=0, rcvd=26, sent=243, time=1,
starttls=1
Jan 28 09:32:32 jcrdevelopments postfix/smtpd[14295]: connect from
unknown[109.181.126.59]
Jan 28 09:32:32 jcrdevelopments postfix/smtpd[14297]: connect from
unknown[109.181.126.59]
Jan 28 09:32:32 jcrdevelopments postfix/smtpd[14297]: setting up TLS
connection from unknown[109.181.126.59]
Jan 28 09:32:32 jcrdevelopments postfix/smtpd[14295]: lost connection
after UNKNOWN from unknown[109.181.126.59]
Jan 28 09:32:32 jcrdevelopments postfix/smtpd[14295]: disconnect from
unknown[109.181.126.59]
Jan 28 09:32:33 jcrdevelopments postfix/smtpd[14297]: Anonymous TLS
connection established from unknown[109.181.126.59]: TLSv1 with cipher
DHE-RSA-AES256-SHA (256/256 bits)
Jan 28 09:32:33 jcrdevelopments postfix/smtpd[14297]: warning: SASL
authentication failure: cannot connect to saslauthd server: No such file
or directory
Jan 28 09:32:33 jcrdevelopments postfix/smtpd[14297]: warning:
unknown[109.181.126.59]: SASL LOGIN authentication failed: generic
failure
Jan 28 09:32:34 jcrdevelopments postfix/smtpd[14297]: lost connection
after AUTH from unknown[109.181.126.59]
Jan 28 09:32:34 jcrdevelopments postfix/smtpd[14297]: disconnect from
unknown[109.181.126.59]
---------------------------

Please find my main.cf here:

http://www.jcrdevelopments.com/temp/main.cf.txt

Please let me know if there are any other settings that would be hand to
see.

Thanks

Jon Reynolds

p.s. when I first set this up on a fresh install, it worked, it just
seemed to stop working after a few days without any fiddling from me...
this is the second time I have experienced this working for a few days
then stopping.