Yes, they do. It does sometimes take a few failures for it to kick in though. Gear is a good improvement, but if he needs the gear then he really should just outlevel the content. If the fight is 42, then he'll either be capped at 45 or 46. Either way it's enough to have 4 pieces of AF armor, a lot more health, and some better abilities for the fight.
But again, if he's having issues there he's going to hate life going through the 2.1 through 2.55 stuff.
