This e-mail address used to be just a forwarder to a local ISP.
Unfortunately that service went down a while ago and won't be up until
at least tomorrow. This prompted me to make this into a real e-mail
address through my domain host (registerforless - r4l.com).
That in turn prompted me to reinstall exim4 in the hopes that I could
once again use it to handle some e-mail tasks that I perform on behalf
of some service organizations (sending customized e-mails "from" the
organization to individual e-mail addresses). I use a generic "mail"
name for this, which is also a real e-mail address through my domain host.
I can send and receive e-mail through this address using Thunderbird so
I know the basics of configuring it. Unfortunately I'm bit out of my
depth when configuring exim4 in this case. I was able to get it to
successfully work with without ssl/tls but when I try to use ssl/tls, it
fails.
Without ss/tls, my server is mail.extremeground.com:587. I can send
e-mail this way but in order to use ssl/tls, my smtp server is in the
r4l.com domain and uses port 465. I therefore updated
update-exim4.conf.conf to set the smarthost set as
dc_smarthost='<r4l server name>.r4l.com::465'
Following the
https://wiki.debian.org/Exim#Configuration, I set up a
self-generated certificate and added
MAIN_TLS_ENABLE = yes
to the exim4.conf.template. I also added the line to /etc/default/exim4
to listen on port 465 and set the port in the .template file then
updated the exim4 configuration and restarted the service.
I've tried using s-nail to send test messages since it allows you to
override the "from" header as such:
s-nail -s 'yet another test as regular user' -r mail@???
garydale@??? < garydale.text
This should be the simplest case - the from address is the address I'm
trying to use and is also the e-mail address I mentioned in the
certificate. Unfortunately my mail goes nowhere.
I've done some playing around with swaks and with the certificates to
try various things but without luck. I tried this several years ago with
a different e-mail provider and got similar results - I could send
e-mail without ssl/tls but not with it. Back then, the provider needed
STARTTLS. I was hoping this would be simpler...
Any ideas?
