Narrowed down my issues with trophies not being awarded upon requirement completion. Basically if you're spamming dice rolls and fast-forwards (X button and O Button after) it will infinitely save your game.
You'll notice the little disc in the bottom corner spin forever, once this happens your game is glitched and you must Quit the game to XMB and reboot it. I've been able to reproduce this 5/5 times now easily.
Going to try playing with auto-animations to see if that helps or makes the problems worse.
- Also happened doing that too
not sure what's triggering it to be honest, seems to happen more frequent when after 25-30+ rolls for me.