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Skill Challenges for 5E, Part 6

Skill Challenges for 5E, Part 6

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.

This final entry to the Skill Challenges series offers sample skill challenges for a DM to take straight off the page or use as a starting point to create their own!

If this series is new to you, go to the beginning to catch up!

The Trek

The PCs must venture across a threatening mire. They make checks to avoid taking damage on the way to their destination. (This skill challenge has a fixed number of checks, regardless of success or failure—but each failure causes PCs to take damage.)

Read Aloud: The map didn’t say anything about this. Between where you are and where you want to be to is a fetid, stinking mire that stretches as far as you can see. You’ll need to apply your skills to get across safely and without getting lost.


DC: 13

Goal: Cross the mire as unharmed as possible by making two ability checks for each character with as few failures as possible.

Penalty for failed check: Each character loses 1 hit point.

Benefit for successful checks: If any check succeeds by more than 10 or on a natural 20, characters find an herbal remedy that heals 1 damage for all party members.

The Pursuit

The PCs are looking for an NPC in a crowded city. First, they must find the NPC’s whereabouts. Next, they have to get there before that NPC can escape. If they do that, they might get the jump on her and make their fight against her easier. (This is a standard skill challenge with multiple phases.)

Read Aloud: You’ve tracked the thief who stole the blessed gem out from under you to a port city. Recent storms have prevented ships from leaving, but the waters are starting to calm. You don’t have much time before the seas are easy enough for her to book passage out of here—and out of your reach. Or would she fence the gem and hide out until you leave?


This skill challenge has three phases. In Phase One, the players are looking for information about the thief’s plans. In Phase Two, they must figure out which ship she’s planning to leave on. Finally, Phase Three is an opportunity to gain advantages when they confront her.

DC for Phases One and Two: 12

DC for Phase Three: 15

Goal: Figure out and thwart the thief’s plans with as many successes as possible in three ability checks for each character.

Benefits for successful checks:

  • Phase One: Each success gives PCs more information about the thief’s plans. After a number of successes equal to the number of characters, the PCs discover that she plans to escape by ship. Move to Phase Two.
  • Phase Two: Each success gives PCs more information about the ship and when the thief plans to leave. After a number of successes equal to the number of characters, the PCs learn the name and location of that ship, which is still in the harbor. Move to Phase Three. If they get failures equal to the number of PCs before they get the required number of successes, the thief escapes.
  • Phase Three: Each success gives PCs some benefit when they confront the thief, such as advantage on their first attacks against her, a reduction in the number of henchmen who help her, or ways to mitigate damage from the trap she prepared for them. Narratively, successes in Phase Three should help them bribe the captain she’s planning to sail with, set their own traps, plan an ambush, or whatever other tricks they come up with.

The Negotiation

The PCs are being hired for a job, but the offer is lower than they’d like. They can try to get more through skillful negotiation. (This is a skill challenge with non-binary success/failure.)

Read Aloud: You sit across the table from the regent, who seems to wear a permanent scowl. “I understand that you wish to negotiate the terms, that you don’t feel that 100 gold is sufficient for your services? Well, I’m listening. What would you like?” He drums his fingers on the table expectantly, already seeming bored with this meeting.


DC: 13

Goal: Improve the contract terms by making demands and having the successes to back that up over four checks.

Benefits for successful checks: Each success brings PCs closer to one of their demands. At the start of the skill challenge, have players indicate what their PC hopes to get from the negotiation, then set a number of successes that they’ll need to achieve that. Players must decide what they’re negotiating for before making the checks—but if they’re successful, they can aim for more with later checks.

Examples of appropriate benefits for a number of successes:

  • 1 success: 20 gold more, comparably priced gear, borrowing non-magical gear.
  • 2 successes: 50 gold more, comparably priced gear, help from the local militia.
  • 3 successes: 100 gold more, comparably priced gear, a skilled mercenary to fill a gap in the party’s abilities, a scroll with a 1st-level spell.
  • 4 successes: 150 gold more, comparably priced gear, a scroll with a 2nd-level spell, a common magical item.

The Assisted Sneak

One PC is trying to break into a room at the inn while the others distract the customers. (This is a Spotlight & Support skill challenge with the “Support Sets Stakes for Spotlight” Twist.)

Read Aloud: Through your observations, you know which room you need to hit—now you just have to get in, get what you need, and get out. It won’t be easy with how busy the inn is, but if the other PCs distract everyone, your rogue can do the job without drawing attention.


DC for Rogue: 14

DC range for Supporting PCs: between 11 and 16

Goal: The rogue makes it in and out safely by getting six successes before three failures.

Benefits of successful checks:

  • For rogue: First two successes get them into the room undetected. Second two have them find what they’re looking for. Final two let them slip out undetected.
  • For supporting PCs: Each success within range leads to rogue making their next check as normal. Each success above the range leads to a success on the rogue’s next check counting for 2 successes. Each failure leads to a failure on the rogue’s next check counting for 2 failures.


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.”

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