Free tables Natural 20 — skill checks

Natural 20 Table — Sleight of Hand Skill Checks, d20

A free d20 table for a natural 20 on a Sleight of Hand check in 5e. Twenty outcomes, from solid to legendary.

A natural 20 on a skill check is not a critical success in fifth edition — criticals apply to attack rolls only, and a 20 on a check is simply a 20. Which is why a legendary roll so often feels like nothing happened. This table gives it somewhere to land.

Twenty results written for Sleight of Hand specifically. A legendary Sleight of Hand roll has nothing in common with a legendary roll at anything else, which is why there are eighteen of these and not one.

Roll d20 when a player rolls a natural 20 on a skill check and succeeding quietly would be a waste.

Severity tiers

Each result names its tier, so you can see at a glance how bad a roll was without decoding a colour.

Solid 1–10 — Cleanly done, with something small to show for it.
Impressive 11–17 — Better than anyone expected. Momentum, or an obstacle gone.
Legendary 18–20 — Scene-shaping. The kind of success people repeat afterwards.

The table

20 results. Roll d20.

d20	Result	Tier	What happens
1	Clean Lift	Solid	Nobody noticed a thing. No extra effect beyond a job well done.
2	Nothing Rattled	Solid	You make no sound doing it, whatever you were handling.
3	Took Two	Solid	You come away with a second small item as well, the DM's choice.
4	Left No Trace	Solid	Nothing is out of place. Nobody will realise anything is missing until you want them to.
5	Quick Fingers	Solid	The whole thing costs you no action — fold it into something else you were doing.
6	Felt the Shape	Solid	You learn one thing about the item you couldn't have seen: its weight, a hidden catch, whether it's warded.
7	Planted Instead	Solid	If you wanted to put something into a pocket rather than take it out, that also works perfectly.
8	Steady	Solid	You have advantage on your next Sleight of Hand or tool check this scene.
9	Covered	Solid	One ally nearby is credited with your distraction, and is not suspected either.
10	Knew the Pocket	Solid	You get exactly the item you were after, even though you couldn't have known where it was.
11	Under Their Nose	Impressive	You do it while being directly watched, and the watcher is certain nothing happened.
12	Swapped It	Impressive	You leave a convincing substitute behind. The theft won't be discovered until someone tries to use it.
13	Took the Set	Impressive	You come away with everything of that kind the target was carrying, not just one.
14	Disarmed	Impressive	If the target was armed, the weapon is now yours, and they haven't noticed yet.
15	Blamed Someone Else	Impressive	When it is eventually discovered, the evidence points squarely at a third party of your choosing.
16	Read the Room	Impressive	You learn what else the target is carrying — everything of note, in detail.
17	In and Out	Impressive	You may repeat the same trick on one additional target this scene without rolling.
18	The Perfect Job	Legendary	Nobody will ever connect this to you. Not on investigation, not on divination, not on a confession. The DM should honour that.
19	Took the Thing That Mattered	Legendary	You come away with the one object in the target's possession that matters most to the story. The DM decides what it is, and it should genuinely change something.
20	The One They'll Talk About	Legendary	You lift something that could not have been lifted — from a locked case, a sleeping dragon, a god's own altar. It is yours, it is clean, and the story of it will outlive you.

Questions

Is a natural 20 a critical success on a skill check?

Not by the rules. Criticals apply to attack rolls. A 20 on a check is a 20 — which is why a spectacular roll so often produces a shrug. This table is the house rule that fixes that.

Does a natural 20 automatically succeed?

No. On an ability check there is no automatic success — if the DC is 25 and your total is 22, you failed with a 20.