I keep getting the following fail with heroku + git...
$ heroku jammit:deploy --app XXXXXXXXXXX
===== Compiling assets...[OK]
===== Commiting assets...[OK]
=====
Just force the commit every time you push and it will push it even if there are fast-forward commits. We do this in our development Heroku server all the time since we're all pushing different commits (some further behind than others).
git push -f git@heroku.com:picasso-staging.git
I don't use jammit for deploying, but you could probably get away with force pushing first and then running the jammit task second. Or check and see if jammit supports a force push flag of some sort.