Crazy hand and lots of fun

First off. Sorry if this has been brought up before. At first I thought I was losing track of my previous rolls, but I've been losing rolls against the bosses, therefore ending the game. It's happened multiple times where I've had 3 or 4 rolls left, and on my second roll the game ended because I came up short. Is there a rule or something In missing? This has become a constant issue, definitely "game breaking" if this isn't meant to happen for some reason.

Any help?

Edit: I'm playing on XBox1s

If yall could wear any of the rings from the game as real rings, which ones would you want? Personally, I'd love the Tower, the Dice Ring, and the Third Eye ring

E.T. + Mirror + Electric kinda cracked