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Message: <blockquote data-quote="FormerlyHemlock" data-source="post: 7069644" data-attributes="member: 6787650">If you want players to be uncertain exactly which attempt actually constitutes their "best attempt", another way to do it would be for your first roll to represent your first attempt. If you want to keep trying, the DM secretly rolls another d20: this represents your "best attempt" if you keep trying all day, which might be better than your first attempt (if you get a better idea) or might not (if you're just beating your head against a wall). After that, every time you pay the cost to re-attempt, the DM secretly re-rolls your attempt but caps it at the secret maximum.This way, you can re-try twenty times if you want to, and it might be futile, or maybe the lock actually opens on the twenty-first try. There's no way to know for sure--but most players will probably only retry once or twice at most. If you impose a suitably high cost in time, materials, narrative creativity ("what are you doing differently this time?), or other consequences, they might only retry in emergencies. "We HAVE to get through this door or the trolls are gonna find us--Bombur, could you use the last of your Oil of Slipperiness on Bilbo's lockpicks and see if that helps? If that doesn't work, maybe Gonzo can soften up the metal with a Burning Hands through the keyhole and then Bilbo can retry again?"For purely physical athletic tasks, this isn't appropriate: you're not going to be significantly better at jumping over a chasm than you were the first time you tried. For creative tasks like lock-picking and spell research, where you might or might not get a sudden break, it might be appropriate.</blockquote>

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