@kirby @Inginsub
You can increase Pemorla's own log verbosity to debug and see what's going on.
I have hydroxide ProtonMail bridge thingie running locally, it works as SMTP server, I think I just pointed my Permombler to it, host port, login, password — and it worked, I didn't spend a lot of time on it.
But it might be tricky for remote SMTP server.
@kirby @Inginsub
Another solution might be using sendmail adapter with msmtp — I've never used this setup myself, but check it out, might be easier to pull off than both: working with remote SMTP as is and setting up your own SMTP server to run locally. msmtp uses systemwide certs in /etc/ssl — so this shouldn't be a problem, you need a very basic .msmtprc: host, port, from, user — you can specify password right in it, or put it in .netrc