Sneak Through the Jungle

8 Dexterity but +15 Stealth

Stealth sessions are hard to pull off in D&D.

First off, in D&D 5e you have exactly two things you can do as a player to remain hidden from an enemy. There's rolling a stealth check, and taking the hide action (which is just the combat version of the stealth check). If you want to avoid combat by sneaking around, you better be a pretty powerful rogue character, or it just isn't going to happen.

Second, the system isn't really designed for that sort of play. D&D is very much about combat encounters, fighting head-on, and epic battles. Not that that sort of thing isn't fun, but it doesn't really translate into a stealth-based game. The rules on hiding and obscured vision are scattered all over the PHB, and rogues have to get massive bonuses (seriously, Reliable Talent is one of the most broken skill abilities I've ever seen) to even be able to attempt that sort of stuff.

Finally, there's one little hook in the PHB that really cements the idea that the game isn't about stealth. PHB pg.195: If you make an attack while hidden, you're no longer hidden. And note that it's not just to the creature you're targeting. It's everyone. Even the Skulker feat (which allows you to stay hidden if you miss your attack) doesn't let a low-level character deal with more than a single guard without revealing themselves.

The problem is compounded even further when you get to group stealth checks. Don't have a group full of rogues? It just isn't going to happen.


Troubled youths, the lot of them

So how do you run a meaningful, choice-filled session that doesn't hinge on every player being a stealth master?

Group Sneaking Sessions

This method works best in a city or crowded area. Of course, it can work just as well in a dungeon crawl, but it requires a bit more setup.


Makin' my way downtown...

First off, you want to give your players a lot of reasons to sneak rather than fight. Make the enemies numerous, powerful, or vicious. Put an alarm system in play, such as tripping magical wards or waking a sleeping dragon as the center of the dungeon. Make the activity they are doing illegal, so they can't risk having the local police force turning against them.

Next, you'll need to set up the destination, and make sure the players know what it is. Whether it's a safe house, a cache of jewels, a magic item, or a meetup location, the players should have their goal in mind.

Finally, you'll need a punishment for failure. Loss of Hit Points, Gold, Spells, etc. Any resource that the player has to give up to stay in the game. I recently ran a session using this method within a large city, where the characters had gotten on the bad side of the local militia. They were trying to get to a meetup location without being detected by the militia, within a large city.



This rogue is OUT

Here's the failure table I used. For reference, the average player level for this group was 7.

On a failed check, choose one of the following:

1. Run! Your are winded from the activity and lose 10HP
2. Bribe! Pay a nearby citizen 50GP to cover your tracks
3. Distract! Spend a 1st-level or higher spell slot to make a big distraction

After that, you can start designing the areas your players need to sneak through.

Each area should have a few different options on how to pass undetected. Really use the skill list here! Stealth should be an option only in areas where a character could reasonably go completely undetected. Otherwise, distraction, coercion, and outsmarting opponents should be the way to go.


Distraction: a good rogue's best friend

Here's some examples for different environments this could be used in.

City
Area: a long street bustling with carriages, carefully watched by the Royal Guard

• Animal Handling: release a noble's caged hounds and cause a ruckus!
• Persuasion: cleverly disguise yourself and pass unnoticed!
• Slight of Hand: casually slip an illegal good into a random citizen's back pocket!

Forest
Area: a large clearing of trees, easily guarded by the Witch's Flying Monkey Scouts

• Survival: create a ghillie suit and crawl across the clearing!
• Acrobatics: with perfect timing, leap across the clearing from tree to tree!
• Deception: make the sound of a child crying, then sneak across while they investigate!

Dungeon
Area: A large catacombs, stalked by the Wights of ancient warriors

• Investigation: figure out their patrol pattern and avoid them completely!
• Perception: move slowly, listening for their shuffling footsteps!
• Performance: walk like a wight and hope they buy it!

Castle
Area: the king's banquet hall, dutifully watched by Royal Guards

• Athletics: climb up the wall and pass right over their heads!
• History: of course you're supposed to be here, you're a scholar studying the King's history!
• Intimidation: bully a servant into giving you his Royal Servant Robes!

Just in time for dinner!

You have probably noticed that these "areas" are large, complex locations with a lot of interactable objects/people. I think this is a far better way to keep the game moving and keep everyone invested, since just moving down a single hallway is only fun to the rogue. If I did want to do a hallway scene, I would probably have a large interconnected area of hallways (a central hub of a castle or a maze of alleyways, etc).

Another way to ratchet up the tension of a scene is to have certain checks be "everybody or nobody" situations. If two characters try to pass through the King's banquet hall by pretending to be historians, they better both be up to snuff or they'll both have to pay the penalty for failure. These checks should probably have a slightly lower DC than the alternatives.

Another way you can set up a stealth scene is as a search. Maybe the players know the blood diamond is in the Lich's palace, but they don't know exactly where. In that case, just create areas that are connected to several other areas rather than just making the series linear. In the end, you'll have a very rudimentary map of the areas that the players can use to narrow down their options, if they decide to map it out.

How it played out in my session

You're not invited to their club

In my game, I ran a linear path from the character's safehouse to the meetup location. It was fairly straightforward, and a lot of players failed. However, nobody ran out of resources, mostly because I only used 4 areas before they reached their destination. However, knowing their spells, gold. or HP were on the line certainly gave the players a bit more incentive to pass, and use their skill-related abilities more.

If I was going to run it again, I would probably expand it a bit. I think the fundamental system is good, and the players ran through 4 areas very quickly. I bet I could make more areas and let them explore a bit more in between the areas.

Also, I think it could be fun to expand the options a bit in each area. Maybe they require attack rolls, using tool kit proficiencies, or gaming set/instrument skills. Maybe they could require 2-3 checks of different skills, and the players would have to pass a majority of them to get through. Maybe each player could have a luck point that lets them pass a failed check with pure luck. Maybe that comes back to haunt them later.


Ain't no safe can hold me now

There's a lot of ways to expand the system. Hopefully you can find a way to make it work in your own game!

Thanks for reading!