5 Sleight of Hand Skill Challenges for 5E D&D

Salutations, nerds, and we’re back with another 5 skill challenges for fifth edition Dungeons & Dragons. This time it’s Sleight of Hand’s turn in the skill challenge spotlight and I’m going to be honest with you, this one was kind of difficult because Sleight of Hand is one of those 5E D&D skills characters typically instigate themselves by pickpocketing or trying to pilfer small objects in plain view. However, I wasn’t about to skip this one just because it’s difficult. Be prepared though, because things are about to get a little bit wacky and I’m hoping you laugh as hard as I did about it.

5E D&D Sleight of Hand skill challenges

Monkey See

For this one you have to set up a shopkeeper as having an infamously terrible temper. Have NPCs talk about it or show them blowing up over something in a scene before you pull this one. Then a little bit later have an animal — a monkey in this example but it could just as easily be a weasel — steal an object from their display. The Sleight of Hand check is to return the stolen object without being caught by the shopkeeper.

Use When. You have a player who really likes animals (*cough* me *cough*) or you need something to puncture the tension with a little bit of comedy relief.

Result of Failure. The character might get caught and accused of trying to steal the item themselves.

Old Switcheroo

There’s an artifact on a pressure plate and a character must make a Sleight of Hand check to push it off and replace it with a similarly weighted object super quickly and smoothly so as not to set off a trap! This one is a classic.

Use When. You have a piece of loot in a dungeon or on an adventure you want the party to have but you don’t want them to think they got it too easily.

Result of Failure. The trap goes off. They still get the item but now the room is slowly filling with sand or they have to run from a bolder or it’s raining snakes or…you know, go back, watch Indiana Jones films and pick one.

My Keys!

Either the characters are in a prison cell or they’re trying to break someone else out of a prison cell, but either way they have to lift the keys off of a guard. And of course the Sleight of Hand check is to pickpocket those keys without being noticed.

Use When. Your protagonists have been arrested or the lovable pickpocket they get information from has and nobody is listening when they want this person released from the iron cage.

Result of Failure. If they’re not already in the box with the NPC they soon will be, or they get labeled as troublemaking prisoners and have to spend extra time in the cooler for it. Do people still call it the cooler?

Monkey Do

There’s a street magician whose made a challenge — anyone who can see the card trick they’ve made their signature, figure it out and repeat it earns a significant prize in gold for being the first one to outwit the magician. If you want to get really spicy with this one you can add some other challenges layered on top of it, like Perception to see what to do but this should be fairly straightforward, right?

Use When. The party needs gold or you need a more lighthearted conflict with lower stakes.

Result of Failure. The character doesn’t get the gold and the street performer probably roasts them a little bit.

Butt Scratch Fever

Everyone’s eyes are on the adventurer for whatever reason. They are giving a speech or a Performance. And suddenly they have an itch! The Sleight of Hand check is to scratch without being seen. (Look, I told you this was about to get wacky.)

Use When. A character has gotten up in front of a crowd for whatever reason and you want to get a good laugh around the table about it.

Result of Failure. Someone notices. Maybe a lot of people notice. This might become a running joke. Be careful to pull it on a player who responds well to this sort of thing.

Yeah, you’ll have to excuse me even though I know there’s no excuse for me. I’ll go stand in the corner but first allow me to remind you all to drop your stories in the comments below if you decide to use any of these and as always, stay nerdy!