Home / Delve into the Depths in the Kobold Blog / Skill Challenges for 5E, Part 4

Skill Challenges for 5E, Part 4

Skill Challenges for 5E, Part 4

Skill challenges are a great way to bring the same sort of structure and excitement of combat to non-combat encounters. PCs use different skills as a group to tackle what’s in front of them and achieve success together.

When you run enough combat in any roleplaying game, you learn that you need to throw curve balls at your players to keep things lively. Sure, you can introduce different monsters with different power levels, but if there’s nothing special about the combat conditions and what characters can or can’t do, players get bored.

The same is true with skill challenges. Previous articles offered suggestions for running skill challenges by the book (4E’s PHB2, to be precise) with some updates. This time we present different ideas to keep challenges fresh by changing up the way they work.

Twist #1: Non-Binary Success/Failure

Main changes:

  • Challenges have a finite number of checks, stated at the beginning of the challenge.
  • Successes and failures determine how good the outcome is rather than whether the PCs succeed.

Suggested uses:

  • Negotiation
  • doing something quickly/efficiently/safely
  • keeping costs low

In a traditional skill challenge, the group either succeeds or fails together. But that kind of binary isn’t always appropriate. Many things the PCs want to accomplish won’t be so cut and dry.

For example, when discussing a contract for an upcoming job, the payment amount can be negotiated up. In this skill challenge, players seek the most successes in a set number of checks. With each success, the PCs are promised more money. If the contract starts at 500 gp, each success adds another 50 gp. However, the employer only talks for as long as it takes for the PCs to make two checks each.

A variation is to punish failure rather than reward successes. This makes the most sense with taking damage or extending the time a task takes. For example, PCs might need to hop on rocks across a lava pool. One way or another, each character will reach the other side after two ability checks. But every failure means damage from a misstep.

Another punishing failure might be in expenses. If the PCs need information from townspeople, they can definitely buy the information they need. But each failure means forking over more gold for the goods.

Twist #2: Dynamic DCs

Main change: The target number for ability checks changes.

Suggested uses:

  • When tasks get progressively harder or easier
  • when it makes sense for the roll to be contested

In a traditional skill challenge, the players know the DC for their checks (or at least they figure it out pretty quickly). Here, that value changes over the course of the challenge.

The first version of this incrementally increases the difficulty with each success—and possibly decreases with each failure.

This can work well with financial negotiation: the more successful adventurers are at raising the payout, the less likely the negotiating noble is to add more. Each time the team convinces the patron to shell out more by succeeding on a roll, increase the DC by 2. (That’s a number that feels meaningful without making it impossible for players later in initiative.)

You can also raise the difficulty after each roll (or after you’ve gone around the table once), regardless of whether a previous check succeeded. This can represent the passage of time or a ratcheting tension. For example, the longer PCs distract the guard to keep them from seeing the rogue sneaking by, the more likely the guard is to turn around and get back to work.

Another variation involves contested checks against a sentient being. The player makes their roll, then the GM rolls to see how well an NPC responds. Successes or failures raise or lower their response level. For example, the lying bard makes a Deception check, and then the lied-to NPC guard makes an Insight check against it. Success by the NPC doesn’t mean the jig is up, but it raises the next DC, while failure lowers it.

Twist #3: Skill Challenge Determines Odds

Main change: Successful ability checks determine the odds of success in a final, separate check. Players make a fixed number of checks, then roll an appropriate die to see if the group succeeds.

Suggested uses:

  • hiding or sneaking
  • telling an elaborate lie
  • solving a puzzle with a few options

In a traditional skill challenge, overall failure occurs from failed proficiency checks. Here, players make a fixed number of checks, regardless of number of failures or successes. The total number of successes then determines the odds of an overall success or failure.

For ease of die rolling at the end, use two checks per player. If you have two PCs, use a d4 for the final roll. If you have three PCs, use a d6. Party numbers up to six work well in this way.

For example, if three PCs try to hide from bandits, each PC makes two checks, and the GM records the number of successes. Then, they roll a d6. If the die roll is equal to or lower than the number of successes in the skill challenge, the PCs evade detection. If the die roll is higher, they fail. So if they had four successes and two failures, the bandits discover them on a 5 or 6.

If you use this twist, set the DC a bit higher than normal to maintain tension of the final roll. And if you realize you’ve set the DC too high and the PCs have too many failures, roll a smaller die for the final check. Or, if they get really cocky about their odds, grab a larger die! But let the players have their successes: they rolled them fair and square.

A slight variation on this requires PCs to use a specific skill or two during the check. Of course, in a skill challenge you should usually let the PCs choose their best skills to give them the greatest chance of success—but the final die roll determining outcome gives you some leeway. This variation is especially relevant if PCs do something that requires a specific skill, like Stealth for hiding from bandits or Deception for lying to an interrogator.

Another variation is laying out a set of options for PCs, such as eight possible paths to take through a dungeon, then using each successful check to eliminate one bad choice. When the skill challenge ends, they have a smaller set of paths to choose from. The one they choose could be fraught with peril, a dead end, or the right path. But they’re more likely to pick the right path with more successes.

Mechanically, if all the knowledge they have is the success or failure of the skill challenge, their decision at the end is still random. But players often appreciate that the final outcome depends on their choice rather than a die roll.


Find more ways to make your character unique and effective in Tome of Heroes. More than 20 new races and subraces, 70 new subclasses, new ways to use magic, downtime activities, and more! All playtested and ready for fun at your table!

about Doug Levandowski

Doug Levandowski (he/him) is a freelance game designer and writer from New Jersey. His work includes all of the Kids on Bikes RPGs, a bunch of weird little indie games you can find on itch.io, and, most recently, Home. His ideal rules for a game would read, “Tell a story with friends. Use dice if you want.”

Leave a Comment

Your email address will not be published. Required fields are marked *

Join the Kobold Courier and Earn Loot!

Stay informed with the newest Kobold Press news and updates delivered to your inbox weekly. Join now and receive a PDF copy of Caverns of the Spore Lord

Join The Kobold Courier


Be like Swolbold. Stay up to date with the newest Kobold Press news and updates delivered to your inbox twice a month.

Pin It on Pinterest

Share This
Scroll to Top