I know I should have dirted him, but was feeling wreckless and wanted to roll the dice. I wonder if i didn't hit backstab twice if it might have snuck through in time. I didn't think about his strategy with one exit favoring his flee/return strategy - always figured the biggest benefit of summoning into one exit room is more closed walls to block the walking spam. Perhaps if I was on my toes I could have walked out and waited on him and backstabbed from there, to buy myself a few more seconds when he flees (if I wanted to play sleep roulette, which I don't think I'll ever play intentionally again).