D&D 5E Questioning Nat 20's: Opposing Skills Checks.

[Unwise]

Part of me is willing to legit give them an one-time auto Nat 20 on ANY roll of their choice during the session or future session in that regard basically.

My advice is never try to make anything up to the players in-game. That is not a healthy dynamic. You make calls and the whole table has to respect that and move on with the game. If you get something wrong, let them know later, but you don't owe them anything.

 

[Campbell]

The only D&D adjacent game I am aware of that does anything special on a Natural 20 for a skill check is Pathfinder Second Edition.

 

[iserith]

Actually, I don't think it is - certainly, in 3e skill checks didn't grant auto-success on a 20 (only for attack rolls and saves), and in 1st and 2nd Ed proficiencies were roll-under. I'm not super-familiar with 4e, but a quick scan of the PHB didn't spot an auto-success for skill checks there either.

That said, it was always a common house rule, and appears to be far from uncommon in 5e too.

The person you are quoting is referring to saving throws specifically which is a rule from a previous edition of the game (not all previous editions of the game)

 

[Lyxen]

My advice is never try to make anything up to the players in-game. That is not a healthy dynamic. You make calls and the whole table has to respect that and move on with the game. If you get something wrong, let them know later, but you don't owe them anything.

This. Again, remember that you are not playing against the players but with them, it's not a question of anyone owing anything to anyone else.

 

[Dausuul]

Part of me is willing to legit give them an one-time auto Nat 20 on ANY roll of their choice during the session or future session in that regard basically.

I strongly advise you to not go down this road. Do not start trying to "make up for" mistakes by handing out bennies. This is an unhealthy approach that encourages you to dwell on your errors, and rewards players for catching you out. If I were a player in this campaign, I'd find this very frustrating.

Consider: You are just as likely to make mistakes in the players' favor as against them. Suppose it had been the player who rolled a nat 20 and got an undeserved victory. Would you then condemn them to suffer a natural 1 at some future date? I sure hope not. But if you don't, then you are tilting the playing field hard in their favor: Heads they win, tails they don't lose.

If it is possible to undo the effects of the mistake when you discover it, that is an appropriate solution. If not, shrug and move on. You'll always make mistakes as DM--I do, and I've been doing it for 34 years. Both you and your players have to be okay with that.

 

[delericho]

The person you are quoting is referring to saving throws specifically which is a rule from a previous edition of the game (not all previous editions of the game)

Crap. Yes, you're right, of course. Sorry.

 

[el-remmen]

Actually, I don't think it is - certainly, in 3e skill checks didn't grant auto-success on a 20 (only for attack rolls and saves), and in 1st and 2nd Ed proficiencies were roll-under. I'm not super-familiar with 4e, but a quick scan of the PHB didn't spot an auto-success for skill checks there either.

That said, it was always a common house rule, and appears to be far from uncommon in 5e too.

We were talking about auto-save on saving throws when you roll a 20, which was the rule in 1E, 2E, and 3E.

 

[NotAYakk]

Nat 1/20 being special on non-attack rolls is a very, very common house rule. So common that many don't know it is a house rule.

A suggested variant, to make it non-automatic, is that when you roll a 1 or a 20, you roll 1d20 or 1d12 and subtract/add that to the roll. It happens rarely enough and matters rarely enough that it should add a bit of drama. This die also explodes (but I'd go with the same die size after the explosion; so if you roll a 12, roll yet again). With a d20 or d12, the double-explosion case is so ridiculously rare it probably will never come up, or if it does it won't matter. But the "faint hope" is sort of fun to have.

In the case where the PC beat the other roll by 2, the 1d12 would mean the knight still has a chance to fail. And higher modifiers aren't vetoed 10% of the time by a combination of your 1s and their 2s.

 

[aco175]

My table tends to grant auto success to a nat20. A lot of it is pointless since the DC tends to be 15-20 and PCs have additional modifiers. Most may not be opposed checks though like a nat20 perception and you can give some dialog about how the PC is all, "Duh. Look, I'm on one side of the secret door and now I'm on the other side." (Robin Hood, Men in Tights quote). Make the PCs feel special.

Opposed checks I may go with a +5/-5 or just give it to them.

 

[Justice and Rule]

So while DMing a session last night, there was a situation where the Ranger pc attempted to intimidated a Knight npc. So an Intimidation roll vs a Wisdom check, IIRC. The Knight npc has Advantage due to being Brave and rolled a Nat 20 on the roll to oppose the Ranger. The Ranger, though, was two points ABOVE the Nat 20 result after his roll+CHA modifier. I ruled that because it was a Nat 20, and an astounding success on the Knight's part, he wasn't intimidated by the Ranger. My buddy, who played the Ranger, took it in good stride and understood that a Nat 20 is the apex number when rolling, did mention "Even though I was two points above said 20?"

Fast Forward to today while I'm at home, I'm now wondering if I made a mistake on my part. I'm trying to become a better DM and I supposed that I am gonna be making mistakes. (On the plus side, my buddy's Ranger was able to score the Killing Blow on a Warg boss, after it had reduced him from 40 HP down to 20 hp after missing him for most of the battle, by rolling a Nat 20 and killing it. (So Dice Karma came around and gave me the comeuppance I would say. Plus the Warg boss, despite having Pack Advantage before getting Disadvantage later thnx to fire.)

But now I'm still wondering if I made the wrong judgement call, as a DM, earlier with the Intimidation vs the Opposed Wisdom check. Now I did have it where the Knight wasn't intimidated by the ranger pc, but gave him a slight nod of "respect/appreciation" by recognizing the ranger's skills. Which wouldn't have happened at all if the rolls turned out different and if the ranger rolled SUPER low.

It might not be strictly rules as written, but there's definitely some "Rules as popularly understood" stuff going on. Natural 20s and 1s have a cultural cache in the D&D community such that in close circumstances, it feels weird for them not to be a sort of instant success. It's that one-in-twenty rush you get when you roll one, and it'd be kind of dissonant for it not to succeed on something (outside the most improbable tasks).

I think your decision was absolutely solid. It helps that the Ranger went along with it, but as far as a command decision I think you justified it perfectly well.