I did everything that I could think of to get the new hunspell-en_CA package working with Claws-Mail. Nothing worked, but I did find that if you ditch the hunspell-en_CA package and load the aspell-en package everything will magically start to work. No need to run ./configure or anything... Just restart the application.
If need be, uncheck the checkbox ...
msmtp only works with username and password, example /etc/msmtprc:
# Use TLS on port 465
# Syslog logging with facility LOG_MAIL instead of the default LOG_USER
# Mail account
from yourserver dom0 <email@example.com>
# Host name of the SMTP server
Answer for Alpine email client
Recent versions of Alpine are compiled for Ubuntu with many of the available patches, i.e., enhancements, and these include a feature called "smtp-rules". It's not perfectly well documented, but here is what the .pinerc section looks like for me. It handles email addresses from my employer, from my alma mater, and ...
It is unclear for me what your exact intention was. But it looks like you've setup the IMAP server with implicit TLS, as usually used on port 993. In this case it is expected that the client initiates the TLS handshake directly after the TCP connection succeeded. This means that the client is expected to send the first message (TLS ClientHello) and that's ...