I followed few articles over the pretty attributes on Git 2.10 release note. Going through which upgraded the git to 2.10.0 and made changes to global .gitconfig
Using cygwin, I recently switched to gpg2. Then I had the same problem for signing with git after setting git config gpg.program gpg2.
Try echo "test" | gpg2 --clearsign to see whether gpg2 is working. I found it the easiest solution to just set git config gpg.program gpg, because that works. But you will also get a better error this way - e.g. that you need to install pinentry.