I'm at the end of my wit regarding howto configure Gnus to send mail,
similar to other mail clients I succesfully use, using port 465 and

For starters, gnus seems to refuse to use port 465 when instructed in
for instance (setq smtpmail-smtp-service 465). I find that a bit odd,
but I can live with it, *if* I could get the authentication to work. But
I can't do that either. It's me, I'm sure,

I've turned a famous Internet search engine upside down, and I think I'm
stuck between a not 100 % correctly configured exim on the server, a
borked certificate and a very precise Gnus.

quoting my .gnus (note port 465 replaced now by 25 in 2 places)

(setq smtpmail-debug-info t) ; only to debug problems
(setq smtpmail-auth-credentials  "~/.smtp-authinfo2"
      smtpmail-starttls-credentials '(("mail.hillenius.net" 25 nil nil))
      smtpmail-default-smtp-server "mail.hillenius.net"
      smtpmail-smtp-server "mail.hillenius.net"
      smtpmail-smtp-service 25
      smtpmail-local-domain nil
      send-mail-function 'smtpmail-send-it
      message-send-mail-function 'smtpmail-send-it)

and in smtp-authinfo I have 

machine mail.hillenius.net login (name) password (name) port 465

Yes, again port 465; but it does not work here either..

Using these settings I get, when trying to send email:

STARTTLS negotiation failed: TTLS
250 HELP
220 TLS go ahead
*** Starting TLS handshake
- Ephemeral Diffie-Hellman parameters
 - Using prime: 2056 bits
 - Secret key: 2043 bits
 - Peer's public key: 2048 bits
- Certificate type: X.509
 - Got a certificate list of 1 certificates.

 - Certificate[0] info:
 # The hostname in the certificate does NOT match 'mail.hillenius.net'.

smtpmail-send-command: Process SMTP not running

on the server I get:

TLS recv error on connection from bufo-sapiens.local []: A
TLS packet with unexpected length was received

The certificate on the server is by Cacert, made out to hillenius.net

I have a  (setq tls-hostmismatch nil) at the top of .gnus.

Remember that there is an outside world to see and enjoy.
                -- Hans Liepmann
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