A PC wants to attempt a very hard task (DC 25). It's not impossible that someone could succeed at this task; indeed, other members of the party could succeed. But the PC doesn't have a shot at it, because their modifiers can only get them to a +2 (and no one has provided bardic inspiration, etc.)
Some have argued for the following position: according to RAW, the DM should never call for an ability check in this situation, because a nat 20 would fail. In other words: if a nat 20 would fail, the task is by definition impossible for this PC and the die must not be rolled.
Okay. Now for my actual response to this post.
I haven't seen the bolded part at all in this thread. I have seen a few people say that they will for their game make that ruling, and that IS supported by RAW. The same RAW that I use for gating rolls behind proficiency, also allows for DMs to gate rolls behind bonuses. The new rule about autosuccess on a 20 only applies if an appropriate roll is called for. If the DM is answering the two questions I posted earlier today using the criteria of bonuses and possible success via those bonuses, then it would be inappropriate to allow the PC with +2 to roll for a DC 25 check.
One implication of this position is that the new "nat 20 auto-succeeds on ability checks" playtest rule is entirely superfluous except as a pedagogical redundancy to eliminate a persistent misunderstanding, because DMs should never call for any roll that this new rule would affect in any way.
AcererakTriple6 has expressed this position very clearly multiple times. You wrote some things that made me think this was your position, too. Perhaps I misunderstood.
@AcererakTriple6 has only said that he would rule that way, not that RAW requires it and the DM should never call for such rolls. While it's not my position to gate all rolls behind bonuses like that, I'm also not going allow a roll for anything I set a DC for and a character is proficient in.
What I am probably going to do is set a number between 3 and 5(I haven't decided yet). That will be the luck factor where an auto 20 could succeed. If I choose 5 and a PC is 1-5 short of being able to make the roll with his bonuses, he will still get a roll to get lucky with a 20. If I pick 3, that PC would need to be within 3 of possibly making the target DC.
There's no way in hell a commoner or even a PC with a 0 bonus is getting a roll to make a DC 30 on a natural 20. It's not happening.
The new rule isn't superfluous, but it is subordinate to the DMG rules. It only kicks in on rolls that the DM has deemed appropriate using whatever criteria the DM has chosen.
My position is: RAW do permit ability checks to sometimes be made even when a nat 20 will fail.
Sure, but only on those rolls the DM deems appropriate.
It has nothing to do with whether DMs are also permitted to say to some players, "If I permitted your PC to make a check for this, a nat 20 would succeed; but it is impossible for X or Y reason, so I won't permit it." Clearly, they are not only allowed to do so but should do so for some X's and Y's. But there's very little guidance in the RAW on what "X or Y reason" can or should be here, and there is certainly nothing to indicate that "X or Y reason" must include "because your mods aren't good enough and a nat 20 would fail, even though the task is possible in the sense that other PCs could succeed."
There is very little guidance, and I think that's intentional. This edition was designed to be rulings over rules and the more guidance provided, the more tightly constrained DMs will feel. They leave it wide open for the DM to determine what criteria will be used to deem a roll automatically successful, automatically unsuccessful, or require a roll.