Hello!
I'm using OSX 10.9 and have installed gpg (and gpg2, if it matters) through
homebrew and git-annex through cabal. I also installed
https://github.com/joeyh/git-remote-gcrypt like the UI told me.

Whenever I'm trying to add an encrypted remote through the web UI I get a
lot of "You need a passphrase to unlock the secret key for user:" on stdout
and, obviously, I can't enter my passphrase (If this was the case I wouldn't
make this post to begin with :))
Is this behavior normal? What should I do to work around it?

Yes, I am using gpg-agent. When other applications ask for my passphrase I get
the pinentry dialog from GPGTools, just like I've configured it in
~/.gnupg/gpg-agent.conf, but this isn't the case with git-annex.