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Skill Challenges for 5E, Part 3

Skill Challenges for 5E, Part 3

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.

Last time, we discussed how to run skill challenges and why. Today, we tackle what to do when players try to break the game.

If They Want to Win, You’re Doing It Right

In combat, players try to maximize their attacks, spells, and reactions—even if it means bending the rules. As you use skill challenges to bring the energy and excitement of combat into roleplaying and exploration, expect players to continue that kind of play.

This is good! It means players are engaged and looking for ways to succeed. With that in mind, let’s consider some questions that players ask to try to bend the rules of skill challenges. Ultimately, you decide whether to bend the rules. But there are ways to say yes without breaking the challenge—or to say no without discouraging creativity.

Can we use spells to boost our stats?

With spells like enhance ability or skill empowerment, players can improve their bonuses. Given that spell slots are precious, this is a big sacrifice. It’s also a completely appropriate use of their abilities to play the game, so let them use it.

If you find that these kinds of spells make it too easy, or if you want to encourage players to rely less on magic, make the skill challenge last longer than the spell’s duration. Skill challenges can be more montage than scene. The five minutes it takes at the table for players to find safe passage through the frozen wastes of Brethaar is only a representation of the hours or days that it takes the PCs to do the same thing.

If the skill challenge must take place in a short amount of time, it could take place in an antimagic shield or some kind of ability nullifier, but this is a one-time solution. You don’t want to deny players the cool things their characters can do. The better solution is to let them win! If they can breeze through the challenge by using their abilities in this way, give them their victory. Then raise the DC for next time to account for this tactic in their bag of tricks.

Can I use a spell for one of the checks?

Absolutely. When a player can make the case for using a spell to help them with a check, let them use it. If you’re trying to intimidate an NPC, casting fireball to punctuate a threat seems valid. Or if they’re trying to examine the contents of a room, knock can make short work of some of the challenges.

But instead of allowing the spell to grant automatic success, use it as a bonus to the roll. A good rule of thumb is to add twice the level of the spell to the check. So, if the wizard tries to intimidate with fireball, they’d roll a d20 and add both their Intimidation proficiency modifier and +6 for the spell (double the value of a third-level spell). Or if the warlock searches a room and uses knock to crack open a locked chest, they add their Investigation modifier and +4 for the spell to their d20 roll.

In addition, keep natural limitations in mind to help moderate over-reliance on spells. The room where the PCs are knocking heads might be too small for a 40-foot sphere of burning destruction. Or, there could be guards within 300 feet of the room they’re searching, making knock a surefire way to bring unwanted attention.

I don’t have anything that will work. Can I pass my turn?

Skill challenges involve everyone, so try to keep everyone involved! Chances are, a player who asks this just need a bit of help figuring out how their skills come into play. Respond with a question: why do you want to skip?

If the druid is invested in the Nature skill, but can’t see how to use that in an interrogation, offer some possibilities. Maybe they could use their knowledge of the natural world to see if an NPC’s claims makes sense. How could a character use Religion when searching a room? Perhaps there are artifacts in there that don’t quite make sense given who the room’s owner worships.

Some of this comes back to knowing what your PCs’ best skills are. Since you already need to know those to set a reasonable DC, make sure that your challenges have ways to use them.

Assisting another player is also a good teamwork option. Instead of making a check directly, a PC could figure out a way to help a companion. If the rogue can’t quite see under the desk, the barbarian could use Athletics to hoist it up so they can get under. While that could be a check itself, it may seem more fitting to have that only indirectly affect successes and failures. If so, have the PC describe what they do to assist a companion without rolling; then, give that companion advantage on their roll. If that companion fails though, it counts as two failures toward the group’s total. Players working together face consequences together too.

Can I just do an attack roll?

Just as casters rely on their spells, martial characters like to cast hit something. However, this is the only time where you should just say no. Skill challenges are about exploration or role-playing—not combat. Work with your players to get them out of their comfort zone and help them see how their PCs engage with the world nonviolently.

That said, strong or dexterous PCs can use skills such as Athletics, Intimidation, Performance, and Sleight of Hand to show off without trying to hit a specific AC.

The Takeaway

Remember, when players try to “break” a skill challenge, it means that it matters to them. You’ve done your job as a GM setting up a compelling scene! They’re into it—they just might need some direction. And if they figure out clever ways to make skill challenges too easy, don’t punish them with arbitrary failure. Play the long game and set the DCs higher next time.

Upcoming Articles

The final two articles in this series, will give you alternative approaches to skill challenges: things like shifting difficulties, ways to make them even more collaborative, and non-binary success and failure.


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!

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