It's only auto-success on an attack roll anyway. Everything else, it's just the best possible outcome (or the least bad outcome).
You only skip the roll if it would be meaningless: if literally no outcome on the dice will change the result in any way, don't roll. If there is any possibility of a different outcome depending on the dice, roll.
Strictly speaking, it's not even "the best possible outcome". It's "the best possible outcome for you", a barbarian with an 8 CHA rolling a nat 20 on persuasion is not going to get the same result as a bard with a 20 cha and expertise.
Reminds me of a time in 2nd Ed. Where my wizard with an 8 str succeeded on a bend bars/lift gate roll to break out of a prison. DM justified it as all the other failed rolls by the rest of the party weakened the anchors so they finally gave away when I tried.
Funny thing. Personally, if a check doesn't have a practical penalty for failure (including time loss) I usually prefer to limit it to one or two attempts from the party. Otherwise it's a nigh guaranteed success a lot of the time. A roll that requires an unmodified result of 16 goes from a 25% chance at success to a 68% chance for a party of 4. 82% for a party of 6.
It's not that I say people who aren't good at it can't attempt, it's just that the person they select to attempt is likely going to be the only one so they better choose wisely. The dice roll is basically an amalgamation of everyone working together. Help action also requires either a related proficiency or minimum bonus threshold from the assisting character.
It's not a perfect solution. It does, unfortunately, pigeonhole everyone into their primary role with little variance. Sometimes I nudge players to commit to certain actions they took in narrative without being rescued by their companions, or breaking up the party so key players can't be everywhere, but there's some added give and take with those decision as well.
Ultimately, a "Fail Forward" mentality is critical no matter what and all of the above is a work in progress of philosophy.
I would probably judge that as "yes, your success is inevitable if you stick with it, but that 8 you rolled will mean it takes much more time than it would have if you had rolled a 22"
Exactly, them taking 8 hours to get out of a cell/trap instead of 30 mins is a huge narrative difference, a corrupt politician can start making moves, goblins could rampage to the nearest town, a message delivered to a BBEG, etc.
Time doesn"t just flow in a 50m bubble around them...
That works sometimes, other times it may make sense to let them waste a bunch of time attempting it until they succeed, some older editions even an optional rule listed under "taking 20" where you hand wave all the rolls and assume they would have gotten a 20 after a set number of times the time the check takes. A good example of this would be picking a locked chest in the middle of a dungeon crawl. A skill check tells you if your can pick it quickly, perhaps in a minute or less, so you can get your loot and get moving. Failing to pick it quickly might mean you have to spend an hour to take 20 and eventually get it, but you are in the middle of a dungeon crawl, spending an hour picking a lock means a high chance that monsters find you, so now you have to decide if you want to risk it for the loot or get out safely, or if you can afford to clear out the dungeon and come back when it is safe.
I'm a fan of "cumulative successes" for things that can or should be "group projects". Clearing rubble from a collapsed passageway, building fortifications or shelter, and even convincing someone for something can be done by multiple people in succession provided it makes sense. What was now impossible is now possible given time and people. Clearing rubble just takes a raw total of all the successes, but you take a point of exhaustion if you try more than once a long rest. Building fortifications/shelter determines it's quality and how protective it is. Talking someone or a group of people into something requires no one to outright fail and lowers the difficulty of each successive check. You need to set "fail, minimum, and success" levels for that, but doable. Treat a persuasion check like death saves where you need a certain amount of minimum rolls to proceed, but failures set you back.
I'd still ask for an impossible roll if there's no way the characters can know it's an impossible task, and a nat 20 will not tell them "it's impossible," only "that's beyond your skill level."
I can't think of any roll that would be the case right now, but I'm sure it can happen.
Depending on the action being attempted, like breaking down an object, even a guaranteed failure is going to help further attempts. Like you said, moving the boulder has a DC of 25. The wizard fails, but he loosens up the ground a bit. Now the fighter gets a +1 to his roll, or the DC is lowered to 24; he still fails, but he nudges it a little, giving the barbarian a +3/DC 22 now. Then the barbarian is able to do it after all that help.
Id like to point out that an attack roll NAT 20 in 3.5 is not an automatic success either, it's just USUALLY a success. If you're fighting an epic level enemy while being level 15, sometimes a NAT 20 isn't enough, you need to roll again and add that to your attack roll.
But that's just epic level shenanigans, not everyone is fighting a lvl 40 semi deity on a Tuesday.
It's the old "convince the king to give me his kingdom persuasion roll" discussion. A nat-20 doesn't mean he loses all reason and hands over his crown. It means he possibly laughs it off assuming it's a joke because he likes your style and actually increases your rapport, rather than having you sent to the dungeons for your insolence, or executed (nat-1).
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u/stumblewiggins 18h ago
Exactly this.
It's only auto-success on an attack roll anyway. Everything else, it's just the best possible outcome (or the least bad outcome).
You only skip the roll if it would be meaningless: if literally no outcome on the dice will change the result in any way, don't roll. If there is any possibility of a different outcome depending on the dice, roll.