Debian wheezy had a version of exim4 whose number was 4.7x, maybe even as high as 4.79. With a little help, I got exim to establish a smtps session with the internet service provider in our area. The recipe was to:
dpkg-reconfigure exim4-config and be sure to select mail delivered by smarthost and received via fetchmail or something comparable. set passwd.client as follows: *.suddenlink.net:marti...@suddenlink.net:somePaSsword It was also necessary to add a line to /etc/exim4/conf.d/transport/30_exim4-config_remote_smtp_smarthost in a certain place that indicated protocol=smtps and then the TLS magic worked for about 3 years until I upgraded to debian stretch using exim4 version 4.89. Then the magic black box broke. In the first place one can not add protocol=smtps to /etc/exim4/conf.d/transport/30_exim4-config_remote_smtp_smarthost as this throws an error now that protocol=smtps is not understood. Okay. When I leave that out, the conf.autogenerated file generation code is happy and produces a conf.autogenerated that indicates we are using port 465 which is true and that the smarthost is smtp.suddenlink.net which is also good but attempts to communicate with that host now end instantly as in the following from /var/log/exim4/mainlog 2018-05-28 19:32:15 1fNL0J-0003CQ-70 H=smtp.suddenlink.net [208.180.40.68]: Remote host closed connection in response to initial connection 2018-05-28 19:32:15 1fNL0J-0003CQ-70 == mar...@okstate.edu R=smarthost T=remote_smtp_smarthost defer (-18) H=smtp.suddenlink.net [208.180.40.68]: Remote host closed connection in response to initial connection 2018-05-28 19:32:26 1fNSVt-0004AS-HE H=smtp.suddenlink.net [208.180.40.68]: Remote host closed connection in response to initial connection 2018-05-28 19:32:26 1fNSVt-0004AS-HE == wb5...@arrl.net R=smarthost T=remote_smtp_smarthost defer (-18) H=smtp.suddenlink.net [208.180.40.68]: Remote host closed connection in response to initial connection I looked in exim's archives in the newer messages and didn't see anything promising. A search box, there for certain terms such as smtps and version 4.89 would be nice as this would probably drill right down to where one needs to go to get the setup right. You may wonder; How am I sending this message? I installed a bare-bones application called msmtp which does TLS connections and I can once again get to the suddenlink server. It just works but it is not a substitute for getting exim4 version 4.89 using the same smarthost. In the first place, msmtp is no good at all at delivering local mail such as when one of one's carefully-written cron jobs or other applications gets in to trouble and cries for help. Right now, I can compose an email message using nmh and cat that file to msmtp by creating a link to it called sendmail and then cat the message to the fake sendmail with the -t flag to strip off the addresses. I suspect the suddenlink.net server is fairly average so if I just knew what exim needs, I can make it happen but that kind of documentation for the newer versions seems hard to find. Here is what I had to tell msmtp to make it work: tls on # Don't use starttls. tls_starttls off tls_trust_file /etc/ssl/certs/ca-certificates.crt from marti...@suddenlink.net protocol smtp port 465 # The SMTP smarthost. host smtp.suddenlink.net user marti...@suddenlink.net password ThePassword I did try exim4 -d -M msgid but the failur message about the server closing wasn't any more detailed such as; What di I send and what did the server do after that? These are usually essential parts of debugging and TLS is a black box that even if you know basically what it is doing, when it goes wrong it is like the "Check Engine" light on a car. Thirty-thousand parts humming along and one of them has gone bad. Go figure! I would be happy with having enough plain English instructions to make the black box work again so exim4 can do it's great jobs of handling both local and external messages. Many thanks for any and all constructive suggestions. Martin McCormick -- ## List details at https://lists.exim.org/mailman/listinfo/exim-users ## Exim details at http://www.exim.org/ ## Please use the Wiki with this list - http://wiki.exim.org/