I sign all my mails with GPG for a few years now. Beside the huge hypothetical boner and the moral highground this provides it is also nice to get some minor benefits like a ham bonus on Debian mailinglists (even if we all know how that is implemented).
It is hard to belief sometimes, but I don't sent mails to Debian only through. Sometimes I get questions what that strange attachment is nobody can open. Its okay through, I don't blame them.
What I can't tolerate through is mails from me ending up in Spam because I don't sent mails from one of the big (free) mail providers (and to a bunch of people all at once). There are a bunch of options available to make my mails look a bit more legit even for those mailservers which don't understand gpg in the form of SPF, DKIM and DMARC. The bonus they provide isn't huge (if not non-existent) and there are problems and shortcoming involved I don't have to deal with with gpg signing but the things you do to avoid having to hear a "lets all just use a facebook/whatsapp/whatever group for communication"…
[note that I have added most of this to kalnischkies.de, but the setup was initially setup for and tested on an other domain – I will just say example.org here to not have you confused by blogpost vs. reality]
Easy to do if you have just one place you sent mails from – which in my case is true as I sent mails by letting msmtp connect to the SMTP of my hoster, which for rough emergencies also has a webfrontend so all I had to do is add a TXT record in DNS: "v=spf1 mx -all".
And as I have subdomains (for mailinglists mainly) which sent mails, too, add for all these subdomains "v=spf1 mx:example.org -all" as well. Additionally, if you have subdomains which do not sent mails, you can say that they all should fail spf unconditionally: "v=spf1 -all" (You can set this also for subdomains you don't have, but spammers use anyhow).
Is a bit harder. My hosts SMTP doesn't support it (they are equally dubious of its usefulness as I am), but don't fear: I can add a DKIM signature locally before passing it on the hosts SMTP! Arch user 2ion has documented his setup and mine is rather similar, just that I installed python3-dkim, took dkimsign.py from git (changing interpreter to python3) and adapted my already existent sendmail wrapper [= a forgot to attach attachement detection script] to use that python script.
Of course, I had to generate some private keys for this exercise. I used "opendkim-genkey -b 2048 -d example.org -s mail" for that (the default keylength is 1024 – the spec seems to suggest that implementations are required to support up to 2048, so if I have to do it, lets do it big). The "-s mail" part is freely choosable by the way for keyrollovers and stuff. Beside the private key that command also generates a textfile which contains what has to be added as another TXT record in DNS.
That's easy again: Yet another TXT record in DNS: "v=DMARC1; p=none". I think I will eventually use more stricter settings and might even explore the report facilities but for now that seems to work okayish.
Sending mails to a Google Mail account (as they make use of those features and add results to mail headers) can tell you if its working. Mail-Tester is also a nice service to test your setup (even through it targets mostly at newsletter creators) which tests various details, presents it friendly and even gives some tips (if it works that is, sometimes it seems to have problems).
A bit of busy work and I see how that could be oh so much more complex if I would have a different setup, but in the one I have it seems to have a very slight net-benefit, even if I would like to not need it in the first place…
On the upside, it gives me another bunch of ham bonuspoints on Debian mailinglists, which means I can probably spam quite a bit now… 😉︎
I just hope I also get enough bonus points on setups I was setting this up for…