• Justin Handlin

Cloak and Dagger DnD Adventures

Crit Academy discusses running Cloak and Dagger style Dungeons and Dragons adventures. In Dungeons and Dragons, there is a myriad of ways to go about building adventures, most follow a simple dungeon crawl. Wander through a dungeon, slay monsters, and loot treasure. While this is good and fun, sometimes we need more, a change of pace. Cloak and Dagger style adventures are more about sneaking into an evil baron's mansion and slaying him while he sleeps, as the adventures can't take on his massive contingent of guards. Or planning to poison the baron during dinner, or having the balcony "collapse in an accident" when he walks out onto it. We discuss this and many more techniques for running a Cloak and Dagger Adventure.

Objectives for running a DnD Cloak and Dagger adventures:

A simple example is to sneak into an evil baron's mansion to slay him. Too many guards for a direct assault.

  • Is there a secondary goal?

  • What method is to be used?

  • Do the players choose? Or does the employer decide?

  • Poison by his favorite dish?

  • Decapitation? Head as proof of your success?

  • Hanging? Set it up to look like a suicide?

  • What happens when they succeed at their task, but leave behind evidence?\

All of these things are important when designing a very cloak and dagger adventure.

The purpose of stealth is to remain undetected:

  • Hiding behind objects,

  • Putting on a disguise or glamour spell

  • Bribery

  • Bluffing

  • Distractions

When setting an objective, these various tools of stealth need to be the weapon of choice to overcome an encounter, not the sword. So make sure there are plenty of options, besides just stabbing stuff.

Players should always have these options available when dealing with a challenge. If you’re trying to push them towards this sort of challenge, then it needs to be multilayered.

Skill challenges are great for these.


For those who use a grid, remember the world is bigger and has far more detail. The details become extremely important when describing the setting.

  • Patrolling Guards

  • Barrels to hide in

  • Rafters to climb and walk across

  • Rooftops to sneak

  • Ladders and poles for going from building to building

  • Horse stables for distractions

  • Traps become even more important

  • Hunting wolves make for great challenges

  • Large crowds to hide in (both enemy and ally)

  • Lighting should become a huge factor in these sorts of games.

Chase Sequences:

What happens when the adventurers are caught in the act?

Once discovered the need to escape becomes critical. Maybe the strength of the enemy is far above the small infiltration team's ability to handle outright. Does a guard catch the PC’s adding something to a drink? They have a few options, engage and fight, and potentially attract more reinforcements, or run. If you’re pushing for cloak and dagger, then, they may be able to take out the single enemy quickly enough before he can sound the alarm. Ok, well now what do they do with the body? In either case, the players could end up in a situation where the need to skedaddle.

Only I can stealth:

Many other skills come into play into a cloak and dagger encounter that don’t rely on simple stealth.

  • Information gathering

  • Starting rumors

  • Disabling or distracting a guard long enough for the sneaky guy to get in.

  • Think about heist movies. Each person has a job to do.

  • This is a great sort of encounter where you can separate party members and send them off to do their own thing. Their success could then determine the chance of success of the next player.

  • Maybe it's one player's job to persuade a target to a specific area at a very specific time.

  • A player could be responsible for ensuring the gate stays open if an alarm goes off.

  • Mages can be responsible for disabling magical traps.

  • A ranger or druid could deal with the hunting dogs/wolves.

All these things have to go right(or at least most of them) in order for everything to go off without a hitch.

What happens when they fail?

Remember, the story should move forward in some way. For instance, if the mage fails to disable a trap, does it go off? If it does, does it draw attention?

If the player fails to get the gate up when the heroes are escaping, what do they have to do now? Attempt to scale the wall? Easy enough for a rogue, but what about the paladin?

No matter the challenge, always be ready to look for another way out!

Unearthed Tips and Tricks! We bring you new and creative content for you to bring with you on your next adventure!

Character Concept:

Muscle Magic

This character from a meta standpoint is a caster such as a Sorcerer, maybe even multiclass into monk for more flavor. A goliath or dwarf would be great race choices.

This character treats their magic, like amazing feats of strength. Their punches and kicks are so powerful they tear thru the weave and distorting it, creating powerful effects.

Wizard: ...was..that...firebolt?

Sorc: what? No. I just kick so fast, that the friction from my foot heats up the air around it, sending a heated shockwave of searing air at my foe.

Wizard:...right. How are you able to shrug off those blows so easily. Mage Armor?

Sorc: That...my friend, is pure, unadulterated...Muscle Magic. I flex hard enough, my muscle glistens in a magic sweat. Protecting this marvelous mountain-like structure from harm.

Wizard: I….don't think...that’s...what's...happening.

Wizard: Ok now that was definitely acid splash!

Sorc: What? My spit? When you have muscles like these, you need to eat a variety of things to keep them healthy. A powerful stomach and spit to meltdown and sustain such a rigorous diet. Thus, my spit could melt the armor off a knight.

Wizard:...I give up….I can’t believe I went to college for this...

Monster Variant:

Barrel Dragon

Origin: Tyrannosaurus Rex


Beast to Construct

Damage Immunities: poison

Condition immunities: charmed, exhaustion, frightened, paralyzed, poisoned

Legendary Action:

The barrel dragon can take 1 legendary action can be used at one time and only at the end of another creature’s turn. The barrel dragon regains spent legendary actions at the start of its turn.

Cannon Blast:

The barrel dragons claws grip tight to the ground, it lowers its head forward aligning its head, back, and tail straight as a blade. Several parts of its mechanical armor open up and you can see behind them are vents containing fan blades that begin spinning and suck in the air around it. It opens it maw wide with a roar. A large cylindrical barrel extends from the recess of this creature's mouth. A ball of electrical energy can be seen forming in its mouth. It exhales destructive electrical energy.

When the barrel dragon uses its cannon blast, forming a line 100 feet long and 5 feet wide out from the barrel dragon. Each creature in the line must make a DC 16 Dexterity saving throw. A creature takes 8d6 lightning damage on a failed save, or half as much damage on a successful one.

The lightning ignites flammable objects in the area that aren’t being worn or carried.


Stanton Fink.

Children of the Demon

Children in an area have been disappearing in a region. A cult who worships a demon surreptitiously initiates children into their ranks by teaching them demonology and summoning rituals in the form of nursery rhymes and suspicious illustrated picture books.

Magic Item:

Forlorn Hope

It is once said that this item was held in a vault of a powerful spiritual leader. It has been said that it can grant any wish the user desires. It is a small hand mirror with a bronze handle and frame.

This item is cursed sentient item.

It can cast the wish spell once per year.

The user who makes the wish loses their life, but the wish is granted.

The mirror will not grant a wish to a person being forced into casting the wish, magical or otherwise.

If the caster of the wish, makes a self-sacrificing wish. A wish that is only to the benefit of someone else, with pure intention. The wish is granted, without taking a life.

Dungeon Master Tip:

Spice up your game will a little naughty!

Players roll a Nat 1?

Bust out the naughty dice! Make it an encounter they will never forget.

Player Tip: Don’t be a Dick

If you have a long break in between your gaming sessions, write short journal entries in your character's voice to help get closer to your character. It will only help to better immerse you and the group the next to you’re at the table.

These can also be amazing to read long after a campaign has ended.

If you have any feedback, unearthed tips and tricks, or topics you would like us to discuss, please send them to us. You can email them to us at critacademy@gmail.com or find us on Twitter and Facebook @critacademy.

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