I have a very simple desire: to receive and send email securely from my laptop, no matter what it's IP address. I'm making this a bit complicated on myself because I'm running my own mail servers on Debian: postfix for SMTP, dovecot for IMAP. And their configuration is a nightmare.
Last year I got dovecot IMAP security working. I don't really remember how, but I seem to be doing plaintext authentication (bad) over a TLS connection (good). I also remember it taking several hours to set up.
This year's project, necessitated by a DHCP-happy ISP, is SMTP authentication so I can send email. What a pain! these instructions are the best I found, but it left out a few important steps. Like you have to install libsasl2-modules by hand, and the password database copy in /var/spool/postfix/etc/ has to be readable by postfix, not just root. All that took an hour to make work; I gave up trying to get SMTP over SSL working too. Ugh.
Why is all this server setup so hard? Both dovecot and postfix support way too many security options, none of them easy. And then various clients don't support various authentication options (Outlook: I'm talking about you). It should all just work out of the box.