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

5 Stealth Skill Challenges for 5E D&D

Salutations, nerds. We’ve arrived at the penultimate set of skill challenges for fifth edition Dungeons & Dragons. Be proud of me because you have no idea how tempted I was to skip Stealth, go straight to Survival and make a joke about how you failed your Perception checks. I resisted the urge! So today is all about you making 5E D&D NPCs fail their Perception checks, so let’s get to it. As a note, per the usual each skill challenge is geared toward small moments of conflict to show those hard earned skills off and give a little more conflict to situations that would have otherwise gone smoothly. They are not intended as hooks to bigger adventures but as you well know, no plan survives first contact with the players so know your table and be prepared for what they’re likely to do with what you hand them. Now, roll for stealth.

5E D&D Stealth skill challenges

Early Departure

There’s a quiet moment during an event and for one reason or another the party needs to leave. Maybe they’ve just gotten a telepathic message that an NPC requires their help or someone just said something awkward no one has yet noticed applies to them. A Stealth check is required to slip out the back without anyone noticing the adventurers leave before the event is over.

Use When. You want to bring the social awkward to adventurers or they’re trying to duck out of a party or some kind of shindig.

Result of Failure. People stare and remark about how rude the group is being. Sometimes this is more punishment than taking damage.

Draco Dormiens…

Sneak past a sleeping dragon. It could be a lot of places — curled up on a pile of treasure, guarding a tower or just found a comfortable spot out in the mountain where the sun hits just right. But those horns look wicked painful and no one wants to be the bozo who interrupted the wyrm’s nap.

Use When. Adventurers are somewhere a dragon would be and has space to fit a sleeping dragon and you need to slow them getting to their destination a little bit. Or a lot if you have a not-so-sneaky armored character in the party and no way to mitigate this circumstance.

Result of Failure. Roll for initiative.

Stalk of Shame

A lot of parties like to use the debauchery table. In this particular case waking up in someone else’s bed involves having to sneak back out of it again without getting caught by the people in the house. A Stealth check is required to slip out unnoticed.

Use When. Characters rolled on the carousing table and someone awakens with one of the NPCs. This can be great fun but make sure everyone is cool with it first.

Result of Failure. Someone’s got some very awkward explaining to do and there will probably be rumors.

Not Our Gathering

So the adventurers are moving around probably somewhere they shouldn’t be when they come across a gathering of people who very obviously are not them. Everyone is wearing masks or hoods — maybe they’re having an obvious cult meeting — but regardless the characters very much do not belong there and for whatever reason have to get through the room anyway. Hey, they might decide to try to use a disguise kit instead, but that’s just part of the game, right?

Use When. Yoou want to highlight a faction and introduce it in a short way to get them back out later, or you need to slow characters down as they go through a sewer system or something similar.

Result of Failure. They get caught and probably have to make some Deception or Persuasion checks. If all else fails there’s always an initiative roll and a handy dandy cultist stat block in the Monster Manual…

Dropping Eaves

The adventurers are trying to listen in on a conversation in a crowded restaurant. Maybe they’re trying to get information for a quest they’re already on or maybe one of the NPCs said something of interest to a character in the party but either way they know something the adventurers really want to know and the answer to getting it is sneaking around to listen in on a conversation.

Use When. You don’t want the adventure hook to come to the characters too easily or maybe you have information they need and you think just telling them would be too easy or an exposition dump. Challenges!

Result of Failure. Probably getting caught and finding out anyway (because the party’s need to know is the point of this) but also having to spend a night in the brig and possibly break out of it.

So there you have Stealth. I hope you guys join me again next week for the wrap up of this series with Survival checks, and you get some use out of all this. I now return you to your regularly scheduled nerdfest and of course, 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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