You can define multiple recipients. gpg -e -r Recipient1 -r Recipient2 -r Recipient3 Also, for something as simple as your address, you don't need to create a text file (although you may want to for a long message). In the command above, simply hit enter after the last recipient, and you'll see blinking cursor. Type out your address and hit ctrl+d when you're done. Lastly, add the word "armor" to a separate line in gpg.conf so you don't have to type -a in every command. It's not caveman-ish at all. A properly configured gpg.conf makes command line gpg easy.