diana acrobat 5E D&D acrobatics

5 Insight Skill Challenges for 5E D&D

D&D Ideas -- Treasures of the DMG
Play Your Next 5E D&D Game as a College of Ghosts Bard

Salutations nerds. Today we’re going to be rolling some Insight checks. Get ready to cast detect bullcrap without using a spell slot because that’s where we’re headed with this fifth edition Dungeons & Dragons material. For those of you just hopping in with this series the purpose is to give you a set of flash encounters based around a skill challenge you can drop right into your game at any point and aren’t meant to take up too much time or serve as longer plot hooks. The idea is when things start getting slow at your table you can reach for one of these, give some spotlight to a 5E D&D skill and create a little conflict that won’t take over your entire session. So without farther ado, let’s see whose lying.

diana acrobat 5E D&D acrobatics insight skill challenge
Illustrator Robson Michel describes this as a redesign of the Diana character from the old Dungeons & Dragons cartoon. As Diana became older, she learned how to achieve inner balance and confidence, and also how to kick some ass with martial arts. Click the image to see more of this artist’s fantastic work. [Art by Robson Michel]

5E D&D Insight skill challenges

Troll Toll

As adventurers travel along a well trafficked road they find a group of people dressed in ill fitting uniforms who stop the party on their way to ask for a legal toll for passage. By order of the reigning monarch, one of them says with a crocodile grin. The Wisdom (Insight) check to figure out these toll takers are lying through their teeth and completely intend to beat it out of the party if they refuse should be pretty low, since this is the oldest trick in the book.

Use When. You want some quick combat with bandits to break up a long journey because believe you me it’s a rare party that won’t proceed to bash some skulls under these circumstances.

Result of Failure. The party thinks there are legitimate guards asking for a toll. They’re still probably not going to pay it, mind you, but they might end up worrying about getting a legal bounty on their heads from beating up some totally legit agents of the crown.

Sneaking Street Rat

A filthy street urchin comes running up to our illustrious heroes to hide behind them because a man is chasing him for “absolutely no reason.” The clever kid knows how to spin this and act like they’re afraid of being kidnapped. Unfortunately the man who’s after them is fairly well dressed and willing to tell the party exactly what the child stole — an emerald necklace on a gold chain. A successful Wisdom (Insight) check reveals the child to be the one lying, but you might still get some interesting roleplaying out of trying to disarm the situation.

Use When. Once again, things are slow at the market. Can you tell this happens to me a lot? Or if adventurers are faffing around between big plot points and need a kick in the seat of their pants to do something.

Result of Failure. They might think the kid is telling the truth, in which case a street urchin just got a whole lot richer if they’re smart enough to pawn the necklace off to someone who’s actively leaving town.

Street Performer

A street magician approaches the party with a showperson’s grin and pulls a coin out of one of their ears. The magician makes things appear and disappear with relative ease and once the party starts to get into the performance, makes an attempt to pickpocket one of them. A successful Wisdom (Insight) check reveals this shifty magician’s intention before the attempt is even made.

Use When. The party is in town and you’re in a lag moment, or perhaps when you’re not. Imagine the party trying to get somewhere in particular and being waylaid by a very insistent street performer.

Result of Failure. It’ll cost them a couple of gold or maybe a bracelet if you want this performer to be particularly impressive. Warning — many parties will try to come at this person after the fact so be prepared for them to flee if you run this one.


There’s a person on the other side of a crowded street leaning against a post and flipping a coin as they survey the people walking back and forth. This observer eyes up who is flaunting their wealth and who doesn’t have their purses carefully guarded. A successful Wisdom (Insight) check reveals the observer is looking for a mark to either mug or pickpocket and allows the party to intervene before it happens.

Use When. You want your party to feel like big heroes for interceding on someone’s behalf, or you want to test their morality. This is particularly good for when the rogue goes off on their own, to see if they land on honor amongst thieves or doing the right thing.

Result of Failure. Some poor sap gets mugged. Maybe the heroes intervene at this point once the target has lost a couple teeth and gotten bruised up.

Ale Street Hussle

A local gang leader thinks a large orcish bully is trying to muscle in on their territory because the orc has been in a well trafficked tavern every day for the past week looking tough and running off this gang leader’s thugs. The gang leader asks the party to do something about this orc. Upon arrival they find the orc leaning on the bar and chatting up the server. A successful Wisdom (Insight) check reveals the orc isn’t intending to run off these gangsters at all, they’re just sweet on the server. From the server’s own body language it looks like they’re not disappointed with this circumstance.

Use When. Your party finished what you had planned way earlier than you thought they would and you need to SOS something simple for them to solve. Expect this one to take a smidge longer than the others — there’s being hired, then realizing what’s happening and finally disarming the situation.

Result of Failure. Whatever the adventurers decide to do to this poor orc who is simply flirting with a server.

All right, we’ve hit the end of our Insight checks and if you’ve passed yours, you know what time it is. Of course if you decide to use any of these please let me know how it went for you in the comments below because we all know the adventure never survives first contact with the players. And of course, stay nerdy!

Digiprove sealCopyright protected by Digiprove © 2020 Nerdarchy LLC
Follow Megan R. Miller:
Speculative fiction writer and part-time Dungeon Master Megan R. Miller lives in southern Ohio where she keeps mostly nocturnal hours and enjoys life’s quiet moments. She has a deep love for occult things, antiques, herbalism, big floppy hats and the wonders of the small world (such as insects and arachnids), and she is happy to be owned by the beloved ghost of a black cat. Her fiction, such as The Chronicles of Drasule and the Nimbus Mysteries, can be found on Amazon.
Latest posts from

Leave a Reply