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I can provide a bit more info after redoing the fight: the softlock specifically happened by defeating him as he was preparing the big item throwing attack, which gives a plank to go to the bottom part of the arena.

Defeating Captain Bones (probably) before his head flies off seems to softlock the fight. I think this might happen because the game doesn't know how to react to Captain Bones still having his full body while at 0 hp, but that's just speculation at my part.