Shoot the Moon – Why a 20 Doesn’t Always Mean Success

If you spend enough time browsing Twitter or the various D&D Subreddits, you’re going to run into a lot of stories that are kicked off with natural 20s. I’ve read about crits that landed bards in bed with Lolth, allowed fighters to lift entire castles above their heads and caused the cleric’s god to manifest in person and give them a high-five.

Now, a DM is allowed to run the game any way she chooses but the rate at which these stories crop up – and the exasperated tones with which some of those DMs talk about them – makes me worry that people are getting caught up in the confusion surrounding what happened when someone rolls a 1 or a 20.

Miracle Machines

The most important thing to realise is that the official rules don’t have any concept of a critical hit or miss out of combat. As far as they’re concerned, rolling a 20 just means that you get to add a big ol’ number to your modifier without any other benefits.

Many groups choose to houserule this away without really thinking about it, and instead use some variation of the critical rules used in combat (it’s worth noting that 5E doesn’t even have critical misses as standard). However, there are several damn good reasons why the official rules work as they do.

For a start, while it’s always theoretically possible for you to land a hit in combat, not everything a player can attempt can actually succeed. The classic example used to illustrate this is that no matter how well your ranger rolls he can’t shoot the moon with his longbow. Unless he is secretly Corellon in a wig and sunglasses, I guess.

And even if things are technically within the realm of possibility, you also need to consider that a character has a 5% chance of getting a crit every time they attempt something, so the results don’t always have to be spectacular. A natural 20 can be the catalyst for something pretty damn unlikely, but shouldn’t automatically produce one-in-a-million results.

This is especially true if the check they’re trying to make is repeatable. Sure, it may be possible for the rogue to enter the safe combination by pure luck, but minor miracles like that should not be manifesting at a rate of one per two minutes in game.

If we’re going to be picky, we should probably note that a player shouldn’t really be rolling at all if there’s no chance that they can succeed. However, the nature of ‘I-roll-arcana-okay-I-got-a-17’ players means that unless you run a tight ship those rolls are probably going to happen regardless of the DM’s wishes.

Also, sometimes the DM would want them to make an attempt anyway, either because they don’t want the players to know that what they’re attempting is impossible (such as when they try and deceive the wizard who was secretly scrying on them the whole time) or simply because they want to work out how badly the character failed (did they jump far enough across the mile-wide canyon to land in the river, or will they splat onto the bank?).

You’re an Utter Bastard, Mr. Ambassador

Things are a little more complicated down the bottom end of the results table. Assuming that there’s a reason for a player to be rolling at all, a 1 should indeed be a failure.

However, should it be a critical failure?

On the one hand, having the assassin knock over a suit of armour while sneaking through the castle certainly make things more exciting and dramatic. On the other, sometimes this way of thinking creates utter absurdities.

One story that crops pretty regularly involves some high-charisma bard or warlock rolling a one as they engage in idle conversation with the king, prince or ambassador. Rather than simply failing to persuade the dignitary to their way of thinking, they somehow mangle a phrase of Elvish and end up implying that their wife resembles Gibbering Mouther but lacks any of its charm.

This can be a great way to drive the story in an unexpected direction, but it’s also infuriating on several levels. For one thing, a talented diplomat should be able to speak some honeyed words without running a 5% risk of accidently calling someone rude names. If I were to try and catch a baseball I might drop it occasionally, but I wouldn’t break a finger every 20 balls.

Similarly, if the DM is the kind to make players roll for almost everything, it can lead to utterly immersion-breaking situations. Suddenly trained athletes are failing to make jumps an arthritic grandmother could manage, while the druid is seized by the belief that the best way to tame a wolf is to douse it with fire.

Of course, a little absurdity in the game isn’t always a bad thing. Many parties enjoy the weird and wacky hijinks caused by critical successes and failures, but even then they can make a character feel weak and useless, especially if the failure came at a discipline that they are mechanically and narratively supposed to excel at. Having a character act like a total embarrassment simply because of a bad dice role can really undermine the player’s enjoyment of the game.

Play it Your Way

One final point is that you should absolutely feel free to ignore everything above if you want to. If the group and the DM are happy with it then there’s no reason to stop 20s warping reality for the sake of fun or 1s setting off a chain of Chaplin-esque misfortune.

However, even if you’re happy with playing that way it’s still worth noting that it’s not ‘by the book’, especially as there seems to be so much confusion over this online.

There’s no reason not to shoot the moon, but you shouldn’t do so with the expectation that you’re going to hit it.

Tips for players:

      Remember that your character is part of the game world and has at least some understanding of their own limitations. Would they really try and convert an arch-priest of Orcus mid-battle?

      Don’t roll skill checks when your DM hasn’t asked you to. If you insist on rolling for something trivial they may feel compelled to make you fail a mundane task if you get a bad result.

      Remember that a natural 20 doesn’t necessarily mean that you get the exact result you wanted, even if it is achievable.

Tips for DMs:

      Work out how you’ll be treating 1s and 20s in skill checks before you start playing, and let the players know this.

      Don’t make players roll to do things that are trivial or impossible.

      If you are playing with critical skill checks, always be prepared for that one role that can completely change the game.


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