If this isn't popping try deleting your save from the console.Then start the game and it should start trying to sync with the cloud,Don't allow it to if you click B it should give you a choice whether to try again or play with out being synced.Then start a new game and tracking of the achievement should resume (It did for me).This should work with any other achievements that weren't working.Also I recommend doing this after you've done all the other achievements because it might mess with the save that's on the cloud