There’s been a lot of contentious talk in my feed about building skills challenges in 5th Edition Dungeons and Dragons. Firstly, we need to develop a common understanding of what a skill challenge is in 5e. Secondly, we must get past the issues people have with 4th edition that make them so polarized. Thirdly, we need to focus on how different ways of resolving skills affect pace and tension. Moreover, we need to define some meaningful circumstances that let players drive the use of skills in creative ways. In these ways, we provide creative opportunities to do more than fight, and develop richer games in the process.

What is a Skill Challenge?

A skill challenge is an encounter that allows players to creatively use skills to make progresses and build tension. To be sure, you do not need to require a complex skill challenge in most cases. However, when the scene calls for them, a well crafted skill challenge does for narrative what combat does for action. This means it creates a sense or risk, a way to measure progression, and a clear set of consequences. In other words, skill challenges are every bit as engaging as any other element of the game.

4e Skill Challenges, What’s all This Then?

The main complaint I see about 4th edition skill challenges is that it was a tedious checklist. Rather than a fun game mechanic, it made players feel they had to jump through hoops to complete a task. Indeed, they saw this design more like canned dialog choices in video games than freeform creative problem solving. Undeniably, skill challenges are presented like this in some 4E modules. A point often overlooked is this was not how skill challenges are presented in the 4E PHB and DMG.

I read 4E more kindly, and believe the designers intended these skill challenges to be creative and freeform. However, they also needed to provide DMs with some default structure and progression. Therefore they presented a list of skills to use if some other idea didn’t occur at the table, counting on the DM to disregard it if needed.

Regardless of what it was, what skill challenges should be fun, or at the very least, fast.

Proficiency in Skill Tools

A group of adventurers leaning over a table, seemingly confused by a map they are looking at
Image credit Wizards of the Coast

Skills suffer from a bit of combat rules evy. In brief, skill use is so contextual and complex it defies the procedural rules used for combat in 5e. In spite of that complexity, skill resolution is relatively light in terms of guidelines when compared to combat. Due to this space inequity, people often assume combat is more important for play in 5e than skill resolution. Although combat is a strong part of most D&D games, the rules emphasis wasn’t meant to be a statement of priority.

I’m going to talk about some of the ways the rules address skill challenges below. Additionally, I’ll talk about some skill resolution techniques from other games that can be used in 5e. In the end though, all skill checks are basically the same. Which means the DM Sets up the situation and stakes, and the player chooses the action. Then the DM decides what skill resolution method to use and calls for the roll.

Rule Zero – No Risk, No Roll

The first, and most simple method is to not roll at all. If the player wants to attempt something within their means, there is no risk, and can be tried again until they succeed, do not roll at all. Rolling just to roll is a pointless waste of time. Likewise, rolling for something that can’t possibly succeed is a frustrating exercise. Therefore, for most simple requests, just decide what is a reasonable outcome and have that happen.

Batteries Included

There is more material on resolving skill challenges in 5th edition than people acknowledge. Granted, discussions on skill challenges are a bit more spread out across the core books. In particular, Chapter 8 of the DMG goes into checks with several variants and specific uses like Social Interactions or Chases. However, it’s fair to say the DMG is the least read of the core rulebooks and players naturally expect this to be covered in the PHB. Therefore, people miss this frequently and it’s often a topic of confusion.

The DMG generally presents ways to resolve skill checks that mostly involve a single roll. You’d have to look to a specific implementation, like the chase rules, for an example of checks over time with progressive success and failure.

Types of Checks in the DMG

  • Automatic Success – Essentially the Rule Zero I listed above.
  • Straight Roll vs DC – The standard check most of us know, using a single roll against a DC. But a binary pass/fail can be inadequate for extended actions or times when drama or tension calls for something more complex.
  • Success at a Cost – A ‘fail forward’ mechanic, where failure by a point or two still succeeds but grants some hindrance.
  • Degrees of Failure – A roll that has effects by passing or failing by more than 5 points.
  • Critical Success or Failure – An optional rule that counts a natural 20 as an automatic success, or natural 1 as an automatic failure. (You knew skill checks didn’t crit right?)

I personally don’t find a lot of value in degrees of failure or success at a cost. Both rely on a specific value on a single d20 having a particular meaning. Which isn’t reasonable on a flat probability distribution. I hope the dangers of linking an outcome to the arbitrary “swinginess” of a d20 is apparent. However, this is beyond the scope of this post so I’ll save that discussion for another time.

Borrowing From Other Systems

  • Pushing a Skill – Pulled from Call of Cthulhu, it lets you take a single failed skill check and try again at some coast or greater risk. In 5e this could be the danger of catastrophic failure, exhaustion, injury, or some other consequence the DM and Player agree on. When I use these I ask the player to justify by adding something or trying it again in a different way.
  • Progression Clock – Pulled from Blades in the Dark, this is close to traditional 4e skill challenges. Where in, you require success in a particular number of skill checks to progress the storyline. The difference here is the assumption this engages the player to suggest creative uses for skills to move things along. Additionally, it assumes the DM is working with the player to provide interesting narrative progression or tension. The progression clock mechanic provides several interesting variations that can provide a lot of tension in 5e. Some of these include danger clocks, racing clocks, tug-of-war clocks, and more. You can use all of these effectively to create exciting skill based encounters in 5e. This method comes as close as anything I’ve seen to the intention of skill challenges.
  • Dramatic Tasks – Pulled from Savage Worlds, this is party based successes per turn model. This might work with a timed based challenge, but I generally don’t use this as it is linked to pace and requiring the players to have a particular number of ideas a round.

The Greatest Skill System of All time

Okay, maybe not, but I’m biased. I wrote a post awhile back called Progressive Failures and Rising Tension that I’m rather partial to. So, when I need something more than a binary check, I find this method easy to express to the player and not overly complicated. I sometimes combine this method with one of the forms of progression clocks above for a more dynamic experience. In particular, the ability for one player to get another player unstuck or help has been lots of fun when I can get players to use it.

The master stroke is to use the right resolution method at the right time, and get players to work together through it.


When I create what I call a skill challenge, I typically lay out a scenario, imply some risks and let the player try to figure out creative ways to solve the problem. I don’t usually tie myself to a specific number of rolls and I try to let things progress naturally. One challenge in skill based encounters is the notion of time. As opposed to combat, which has six second rounds, the time to resolve a skill is less clear. If I have a series of rolls in an encounter I generally try to keep a similar arbitrary time period per check. This way I can usually be consistent about how much to progress the scene per check in a way that keeps it natural.

In any case, I try to pick a style of resolution appropriate for the scene. I also try to keep pacing in mind, quickly moving through checks that don’t matter, but creating some space to linger in a dramatic moment. Picking the right method for resolution requires a lot of context and awareness of the game. Although it may seem difficult to know which to choose, it’s easy to develop a quick instinct for it after trying a few methods out. So I recommend doing just that.

Look over some of these methods and try to use at least one in an intentional way during your next game. It won’t take long to figure out what methods jive with your style of game and players. Together with a little experimentation and adjustment, you’ll quickly develop a natural way to select the right method for the right situation.