[Pkg-exim4-users] configuring exim4 smtp to use SSL

[Gary Dale]

I'm running a Wheezy/64 server and am trying to get exim4 to send e-mail 
using an SSL connection. My current configuration works when I use their 
normal smtp port (which is 26, not 25) but fails when I use their 
smtp/SSL port (465).

However Thunderbird is able to send e-mail from workstations to the same 
server using port 465 and have SSL/TLS identified as the connection 
security.

My update-exim4.conf.conf file is (replacing <remote host name> with the 
actual name). If dc_smarthost has the port set to 26, mail gets sent. 
However with it set to 465, it stays in the mailq.

dc_eximconfig_configtype='smarthost'
dc_other_hostnames=''
dc_local_interfaces='127.0.0.1'
dc_readhost='<remote host name>'
dc_relay_domains=''
dc_minimaldns='false'
dc_relay_nets=''
dc_smarthost='<remote host name>::465'
CFILEMODE='644'
dc_use_split_config='false'
dc_hide_mailname='false'
dc_mailname_in_oh='true'
dc_localdelivery='mail_spool'

I did add tls_on_connect_ports = 465 to exim4.conf.localmacros, which is 
supposed to cover the SSL on connect issue.

The log for an unsuccessful mail says:
2015-03-14 00:47:44 1YWdzE-0000l6-CR <= <sending e-mail address> 
U=garydale P=local S=1665
2015-03-14 00:47:44 1YWdzE-0000l6-CR ** -r at localhost: Unrouteable address
2015-03-14 00:47:44 1YWdzE-0000l6-CR ** gary at extremeground.com 
R=smarthost T=remote_smtp_smarthost: retry time not reached for any host 
after a long failure period
2015-03-14 00:47:44 1YWdzE-0000l6-CR ** <sending e-mail address> 
R=smarthost T=remote_smtp_smarthost: retry time not reached for any host 
after a long failure period
2015-03-14 00:47:44 1YWdzE-0000lB-Ik <= <> R=1YWdzE-0000l6-CR 
U=Debian-exim P=local S=2720
2015-03-14 00:47:44 1YWdzE-0000lB-Ik ** <sending e-mail address> 
R=smarthost T=remote_smtp_smarthost: retry time not reached for any host 
after a long failure period
2015-03-14 00:47:44 1YWdzE-0000lB-Ik Frozen (delivery error message)
2015-03-14 00:47:44 1YWdzE-0000l6-CR Completed

I use /etc/email-addresses to change garydale to <sending e-mail 
address>. Otherwise the e-mail just bounces.

When I change to port 26 and leave everything else the same, the mail 
goes through.

Any ideas?