What's actually going on is that gpg-agent just has a "pinentry" dependency. The default pinentry is is pinentry-gtk2, which of course depends on gtk and xwindows and all that. But there's also an curses (text mode) pinentry package that satisfies the dependency. That's what you'd want if you're ssh-ing into the machine. If that's already installed, gpg-agent won't ask for anything more.
So the commands are:
sudo apt-get install pinentry-curses
sudo apt-get install gnupg-agent
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