On Sun, Nov 10, 2013 at 01:15:26PM +0000, Chris Davies wrote:
> > IP address or host name of the outgoing smarthost
> > => "mail.messagingengine.com::NNN".
> 
> Should be a single colon, not double. For example, mail.example.net:587

No, this is incorrect. When you run dpkg-reconfigure exim4-config, it
says:

"Package configuration


  Mail Server configuration 
  Please enter the IP address or the host name of a mail server that
  this   
  system should use as outgoing smarthost. If the smarthost only
  accepts    
  your mail on a port different from TCP/25, append two colons and the      
  port number (for example smarthost.example::587 or                        
  192.168.254.254::2525). Colons in IPv6 addresses need to be
  doubled.      
                                                                            
  If the smarthost requires authentication, please refer to the             
  Debian-specific README files in /usr/share/doc/exim4-base for notes       
  about setting up SMTP authentication."

I can also confirm this is correct, since I am using two colons here
to send to a smarthost on 587.



> 
> If you're using 486 (SMTP/SSL) you may need to tweak the TLS entries in
> the configuration file.

Where are you getting tcp 486 as SMTP/SSL from? On my system,
/etc/services lists:

"ssmtp           465/tcp         smtps           # SMTP over SSL"

There is no mention of 486 either tcp or udp in my
/etc/services. Besides that, 465 is deprecated. The port that should
be used for smarthosts these days is tcp 587, and no ISP has a right
to block that. In fact:

"$ telnet mail.messagingengine.com 587
Trying 66.111.4.52...
Connected to mail.messagingengine.com.
Escape character is '^]'.
220 mail.messagingengine.com ESMTP ready
quit
221 2.0.0 Bye
Connection closed by foreign host."

So, the OP should have mail.messagingengine.com::587 in the exim4
config. In /etc/exim4/passwd.client, the OP should have something
like:

mail.messagingengine.com:username:clear_text_password

Greg


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