I don't seem to have the option to "automatically unlock this key whenever I'm logged in" when trying to SSH into another computer.
seahorse-ssh-askpass all installed. The
gnome-keyring-daemon is running in the background as well. I'm not sure why the option is missing.
I've also tried
ssh-add ~/.ssh/my_key and
ssh-askpass ~/.ssh/my_key. I'll get prompted for the private key password, but the password is still required when I follow up with an SSH command.