Recently it was time to refurbish our email infrastructure. For a very long time I was hosting everything for myself, but things don’t get easier and over time even the spam filters couldn’t catch up. Therefore I looked into a number of hosted services, and in the end settled with Google Gmail.
End of last year I ran a test, migrated one of my domains over to Gmail and tried out if Gmail offers all the required functionality. As with every change, not everything works flawlessy, but mostly I found ways to get things working. As example we have different domains, several users, multiple identities (one per domain), other servers (like a webserver) can create emails as well (needs to play well with SPF and DKIM), a number of different email programs, mobile support and more.
Like a few other people, I occasionally (very occasionally) receive encrypted emails. So far that was not a big deal, because mutt can automatically decrypt these emails, and also search in encrypted emails (by decrypting them first). However I plan to change my email setup in the near future, and allow other programs (like Thunderbird or a mobile client) access as well. This does not work well if the emails are still encrypted. Besides, the emails reside on an encrypted filesystem, there is no need for another layer of encryption on disk.
By default, the OpenPGP extension in Thunderbird (Enigmail) sends every encrypted mail as inline text, not as an attachment. Mutt as example does not recognize the encrypted mail but just displays the unreadable binary stuff.
Finally, after (I think) 13 years, I switched my mail user agent from pine to mutt. Not that I like the latter more, it has other problems and/or ways of handling mails which I don’t like. But the (non-existent) pgp support in pine drove me crazy. After configuring a while around, more than 300 .muttrc config lines and some Perl scripts to create send-hooks from nicely configured roles later, I have almost the same behaviour like before.