Surprisingly easy to send myself pgp-encrypted email from a server without thinking about it:
… | { printf "Subject: subject\n\n”; gpg --armor --encrypt --always-trust --recipient zac@zac.us; } | sendmail -- zac@zac.us
Grabs my key via WKD (or keys.openpgp.org), encrypts it, then emails it. In reality I’ll hard-code my key in scripts; this was just testing, but how easy!