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Nerdarchy > Dungeons & Dragons  > D&D Skills 101  > 5 Investigation Skill Challenges for 5E D&D
5E D&D Deception skill check Stealth skill challenge

5 Investigation Skill Challenges for 5E D&D

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Salutations, nerds! Continuing with the theme of five flash encounters for the skills in fifth edition Dungeons & Dragons, today we’re talking about Investigation. So put your detective hats on, get out your magnifying glasses, because we have some small mysteries to solve today. The idea here is to give you a few small encounters based around a skill challenge you can drop into your 5E D&D game to slow the action down and give characters a chance to flex their skills they don’t get to use perhaps as often. Investigation comes up fairly frequently anyway and sometimes it can be nice to have investigation for investigation’s sake. So with farther ado…

5E D&D Deception skill check Investigation skill challenge

Illustrator Robson Michel describes this as a redesign of the Sheila character from the old Dungeons & Dragons cartoon. She’s a thief with a cloak of invisibility. [Art by Robson Michel]

5E D&D Investigation skill challenges

Falling Vase

On a crowded street, a heavy piece of pottery nearly fell on a pedestrian — a pedestrian who happens to be a spoiled noble and insists on finding the person that threw the item. A successful Investigation check reveals faint cat tracks on the window sill.

Use When. As per usual, when things are slowing down in a town scenario though this one can be used in any size town. A big city or a small hamlet, it works either way.

Result of Failure. There’s a very good chance a person gets blamed for this.

Carving on the Tree

The party finds an abandoned campsite and there’s no one to be found there even though all their belongings still linger around. There were three people camping here who appear to have been merchants. The natural things in the area have all been disturbed however, and even though the stones of the fire are still warm there is overgrowth. A successful Investigation check reveals some poor folks tried to make a camp in a dryad’s grove.

Use When. You need something to take up travel time.

Result of Failure. Maybe the characters try to camp there and wind up in combat with some dryads, or a tense interaction of some sort. Even on a success they might end up having to parlay with said dryads.

Trick Door

The door in front of the characters has hinges on this side but there’s nothing they can pull it open with and pushing on the side with no hinges does nothing. A successful Investigation check reveals the hinges on this side of the door are for show and the real ones are on the other side of the door. Pushing on the side with the hinges opens the door.

Use When. You need a simple puzzle possible to solve with a quick skill check.

Result of Failure. They aren’t able to get the door open. If it’s an important door you can be sure characters will figure out something else to try to get through the wall and you can enjoy them face palming when they discover the trick. Basically if they can’t get this door open someone will probably suggest looking for another way in or shaping stone, and allowing this is your best bet for maximum enjoyment.

Stolen Necklace

A noble’s necklace was stolen and they loudly narrow it down to two potential thieves. The noble and their bodyguard stand together glaring at the two thieves. The noble is sure one of them stole the necklace but a successful Investigation check reveals the bodyguard’s defensive posture and how they’ve kept their hand in their pocket the entire time. The bodyguard was the one who stole the necklace.

Use When. Things are getting slow at the local tavern and you want to spice things up a little bit. You know how these tavern scenes can be.

Result of Failure. One of the two thieves gets blamed but a thorough search reveals they didn’t have it. The noble probably keeps complaining about it and the bodyguard gets away with petty theft. But if the thief doesn’t have the goods, they don’t have the goods.

Monster’s Shadow

There’s a monster in the woods frightening off travelers. Watching for a while reveals the massive silhouette in the mist doesn’t move and the mist never seems to clear away from it. Getting closer reveals  the monster in question is just a statue and a successful Investigation check reveals the bends in the statue are spaced so it’s almost certainly pixies or similar fey who crafted it in the first place.

Use When. You want a little side quest to break from whatever main quest you’ve been running. This one might take several scenes and won’t be as quick as the others but it could very well be a noncombat situation and a fun little diversion for your group.

Result of Failure. They’ll probably at least figure out the statue is a statue and not a monster unless you have one of those players who just charges in and attacks. In which case, congratulations! They slay the giant statue and irritate a bunch of pixies. Either way the road will be deemed safe again.

So there we have a set of five Investigation skill challenges for 5E D&D, most of which are of a fairly lighthearted nature. Of course no plan ever survives first contact with the players so if you decide to use any of these please do let me know in the comments below. We recently started a Community Spotlight on our weekly Nerdarchy the Newsletter too and maybe your skill challenge story will wind up there. We want to know what you’re up to around your gaming tables. Did you find inspiration from one of our videos, website posts or products? Let us know! Comment on this post, tag us on social media or send us a message and share your stories and images. We love making all sorts of content for you and we want to hear about your adventures too. You get a special coupon for $9.99 when you sign up for the newsletter too.

As always, stay nerdy!

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Robin Miller

Speculative fiction writer and part-time Dungeon Master Robin Miller lives in southern Ohio where they keep mostly nocturnal hours and enjoys life’s quiet moments. They have a deep love for occult things, antiques, herbalism, big floppy hats and the wonders of the small world (such as insects and arachnids), and they are happy to be owned by the beloved ghost of a black cat. Their fiction, such as The Chronicles of Drasule and the Nimbus Mysteries, can be found on Amazon.

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