• Justin Handlin

Skill Challenges in 5e Dungeons and Dragons

Crit Academy discusses Skill Challenges in 5e by RP Davis.

The 4th Edition of Dungeons & Dragons has its proponents and detractors, and RP Davis has no intention of rehashing edition wars here. Like most players and DMs who have played many (if not all) editions, 4e has its good points, however, and the skill challenge is arguably 4e’s best-kept secret. 5th Edition doesn’t make use of them, and RP cannot for the life of it understand why, except that 4e challenges don’t directly port over to 5e without modification. There’s math involved in 4e challenges (shocker) that doesn’t translate into 5e’s bounded accuracy.

But that doesn’t mean you can’t use them in your 5e game. You don’t need 4e’s math to balance them, for reasons which will become apparent.

This book gives you the background and advice to make your skill challenges fun and engaging. And they add a great deal of spice to your existing 5th Edition D&D game! So don't wait—give skill challenges a try at your table.

Segment 1: In the Realm

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Segment 2: Crit Nation Feedback: Let’s talk about Blank!

Michael R.

Guys, I got a question on role play immersion…

A fighter likely wouldn’t refer to him/herself as a fighter but instead maybe a warrior or mercenary.

What would a sorcerer or a wizard go by if not their class name?

I always think mages in general, but i could see a sorcerer calling themselves a sorcerer. But a wizard I envision they would refer to themselves by the school they focus on. Like a we call wizards who focus on necromancy...well Necromancers.

Examples: Conjurer, Transmuter, Bladesinger and so forth.

Likewise a rogue Cutpurse, burglar or just a thief.

I could see common folk using sorcerer/wizard/witch/mage all interchangeably.

Main Topic: Skill Challenges in 5e

What is a skill challenge?

Simply, a skill challenge is a series of skill checks by multiple characters, where a certain amount of successes spread across multiple skills and characters must be achieved before a number of failures.

Why use a skill challenge?

Skill challenges great when you want to do a multi-step process or deal with a problem that requires more than one contributor.

For example:

  • Tasks like talking around a skeptical noble, shoring up the roof of a mine, sneaking across a city, winning a court case, searching the jungle thicket, tracking down a criminal, gathering information from multiple witnesses, escaping from prison, or figuring out a complicated magical (or mundane) machine?

  • 5e has group checks, but often can’t always accommodate a complicated activity

  • Additionally, 5e doesn’t really only has information on offering XP for killing things, and no real way to calculate XP for non-combat encounters.

Running a skill challenge!

  • Similar to normal checks, but you allow multiple skills and to help determine success or failure.

  • Allows the leverage of PC skills that otherwise, may not be applicable

  • Basically, you’re keeping score: Tallying success and failures

  • The goal is to allow the checks to resolve scenes as they happen and each resolution builds toward a larger goal.

Don’t announce the skill challenge!

It helps keep the narrative flowing - give a sample if necessary

Not just skills!

  • We’ve spoken on draining player resources, skill challenges are great for that. Encourage or recommend the use of magic spells, or items and loot in their inventory.

  • Consuming these can help the players feel the difficulty of the challenges, as opposed to just making a check and failing forward.

  • If the spell can’t grant an auto success, consider giving advantage on the next check made

  • If done over a long period of time, where a player can recover slots- long travel- this should only ever grant advantage to a check, never auto success

Keeping Order and Narration

While there isn’t really any order needed, its advised to try and keep some sort of organization when doing skill checks. This can ensure that everyone gets to be included when possible.

As you work your way thru the challenges, make sure to narrate the results of every roll, good or bad. The attempt is still going to alter the story in some significant way. Fail forward!

The narration should also take into consideration the level of success. Did the PCs blow by the challenge and not get any failures? Did they narrowly pass? Or is it somewhere in between? Ensure that your narration reflects this.

Raising the Stakes!

Every dramatic thing that happens in the game should have clear stakes. Skill challenges formalize those stakes while giving you a vehicle to resolving the uncertainty surrounding them. A success should have a positive impact on those stakes. A failure, whether a particular scene in the challenge or the entire challenge itself, should impose a hazard.

Planning Skill Challenges:

It’s pretty easy to roll your own skill challenges. Due to bounded accuracy, the DCs will be pretty different. Keeping that in mind, you should be able to port a 4e skill challenge over to 5e without much difficulty at all.

It’s important to add as much variety as possible when planning out challenges. Nobody wants to run into the same challenge all the time.

Some examples:

Social challenges revolve around someone trying to get something from someone else, whether that’s a physical thing, a favor, influence, or whatever. Getting that thing is accomplished through threats, negotiations, or trickery.

Hazards revolve around the characters trying to do a physical thing that’s either difficult or dangerous.


Decide how hard and complex it should be. Fourth Edition used a five-tier complexity system for its skill challenges. RP Davis recommends 3 so its in line with the 5e easy medium hard difficulty settings.

Easy challenges are more about how they succeed rather than if they succeed.

Medium skill challenges have interesting stakes where, irrespective of success and failure, the outcome leads in interesting narrative directions.

Hard skill challenges make for great a stake for player agency. When the players try to avoid

other challenges, like using skills to avoid a combat encounter, use a Hard skill challenge.

RP Davis gives you a guide to mixing these difficulties into one cohesive challenge as well as guidelines for determining requisite skills for the challenges.

Determining Success!

Total Victory: Party succeeds and get rewards of the challenge

Partial Victory: Party succeeds but at a cost.

Failure: Party doesn’t get anything and the situation maybe become worse.

If you like this product, check out our 'Challenge Accepted'

This episode is brought to you by our generous sponsor, Kobold Press!


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Character Concept:

Necro Botanist

In episode 74 we discussed the Botanist. This kinda enhances that character concept.

This build is a reflavor for the wizard necromancy spells. Great for lovers of flowers and plants. Nature skill, Hermit or Outlander backgrounds. Give your wizard something aside look and feel.

Undead skeletons are supported by plant vines forming muscles and ligaments. Turning them into multi-limbed monstrosities.

These can be used to create a variety of weapon effects including piercing dmg, bludgeoning, and slashing.

Grim Harvest(Necro feature) your spells leave small black/purple flowers that absorb the life energy of your foes feeding it to you through vines into your body.

Enhance this with a bit of reflavoring of spells:

Find Familiar could be a skeletal owl made of vines and leaves.

Reflavour your fog cloud spell to be an area filled with a lavender-scented thick pollen

Cloud of daggers could be a cloud of razor leaves.

The shield could be a burst of shambling lives and branches.

Monster Variant:

Spore Zombie

Origin: Orgre Zombie

New features:

Morning star is just a bramble of heavy vines branches.

Defensive Spores:

When the spore zombie is hit by an attack. It can use its reaction to launch toxic spores at a creature dealing 3 poison damage to one creature it can see within 10 feet.

Sleep Pollen Aura(1/Day). A 15-foot radius of toxic pollen extends out from the Spore zombie, moves with it, and spreads around corners. A creature that starts its turn in the pollen must make a DC 12 Constitution saving throw. On a failed save, the creature suffers the effects of the sleep spell. If the creature’s saving throw is successful, the creature is immune to the spore zombie’s spore aura for the next 24 hours.


The Negotiation Skill Challenge:

Setup: For the NPC to provide assistance, the PCs need to convince him or her of their trustworthiness

and that their cause helps the NPC in some way.

Level: Equal to the level of the party. Complexity: Medium (requires 6 successes before 3 failures).

Primary Skills: Deception, Persuasion, Insight.

Deception (moderate DCs): You try to encourage the NPC to aid your quest using false pretenses. Characters can cooperate to aid a lead character using this skill.

Persuasion (moderate DCs): You entreat the NPC for aid in your quest. First success with this skill opens

up the use of the History skill (the NPC mentions an event from the past that has significance to him).

Insight (moderate DCs): You empathize with the NPC and use that knowledge to encourage assistance.

First success with this skill reveals that any use of the Intimidate skill earns a failure.

History (easy DC): You make an insightful remark about the significant event from the NPC’s past. This

is available only after one character has gained a success using the Persuasion skill, and it can be used only once in this way during the challenge.

Intimidate: The NPC refuses to be intimidated by the PCs. Each use of this skill earns a failure.

Success: The NPC agrees to provide reasonable assistance to the characters. This could include


Failure: The characters are forced to act without the NPC’s assistance. They encounter more trouble,

which may be sent by the NPC out of anger or antagonism.


Magic Item:


Irish Kilt

I have a magic item suggestion. It's called the Irish Kilt, and appears to be a plain green kilt with a red criss-cross pattern. It radiates enchantment magic, and when you attune to it, you are forced to wear it until unattuned. It has three charges. While wearing it, you can use one charge and an action to do an Irish jig and give up to 5 creatures within 15 ft. Inspiration OR 10 temporary hp. There is a curse to this item, however. If a creature rolls a nat 20 on an attack against the wearer, or the wearer rolls a nat 1 on a save, the wearer must roll a d100. If the amount is lower then the wearer's hp maximum (after suffering from the effect that activated this trait), then the wearer must use their next move action and bonus action to do a nonmagical jig in place. This kilt regains 1d3 charges at dawn, or 1 charge per bottle of beer drank

Dungeon Master Tip:

Informing the Players of Skill Challenges(Source 4e DMG)

In a combat encounter, the players already know a great deal about how to overcome the challenge. They

know that the monsters possess defenses and hit points, and that everyone acts in initiative order. Furthermore, they know exactly what happens when their own attacks hit—and after a few rounds, they have a good sense of the likelihood of their attacks hitting.

But a skill challenge is a different story. When the PCs are delving through the Underdark in search

of the ruined dwarven fortress of Gozar-Duun, they don’t necessarily know how the game adjudicates that

search. They don’t know what earns successes, to put it in game terms, until you tell them.

You can’t start a skill challenge until the PCs know their role in it, and that means giving them a couple

of skills to start with. It might be as simple as saying, “You’ll use Athletics checks to scale the cliffs, but be aware that a failed check might dislodge some rocks on those climbing below you.” If the PCs are trying to sneak into the wizard’s college, tell the players, “Your magical disguises, the deception skill, and knowledge of the academic aspects of magic—Arcana, in other words— will be key in this challenge.”

Player Tip: Don’t be a Dick

Consider using an Alias!

I recently played a Rogue(the first time in a long time for me) and had a blast. Thanks, Johm for running the game. During the creation of my character, it occurred to me that no self-respecting assassin, thief, thug or any person who works in the underground for hire would give out their name all willy nilly like. So during the game, I introduced my character as several different names as we moved thru the game. If you’re gonna run in the underground group make sure to flesh out an Alias for your character. Go beyond just a name, maybe give your persona some unique features to stand out that can be related to your alias. Like your alias always has an eye patch, or is always cleaning their blade or some such. Treat it almost as another character.

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