D&D 5E Skill Challenges in 5e

While I don’t care enough to dig out my old 4e books, I want to point out that the rules compendium includes the rules as they stood in 2010 (when Essentials came out). There was a ton of errata before that point (and I mean a ton – sometimes it seemed 4e was doing errata in real-time).

Skill challenges were almost certainly one of those areas affected, considering they were revised for the – I wanna say – DMG 2.
Definitely, although 2010 is only 2 years after the initial publication of 4e, and DMG2 was even earlier in 2009, so it’s not like the improved and evolved rules were published years later in an obscure online article. The rules were improved very quickly, all things considered.
 

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Whenever the 4e skill challenge rules are discussed, there’s often a lot of misremembered stuff tossed around. The rules don’t prescribe a certain order for the checks, for example, or that everyone has to roll. One player once told me that they didn’t like the rules—yet turns out the player had actually never even read them! Here are the basics of skill challenges from the 4e Rules Compendium:

There’s also advice on allowing suitable powers or rituals to count as successes, and the rules encourage the DM to include a variety of different skills and approaches. They talk about degrees of success, meaning that a good challenge takes into account the number of failures and successes to determine the final outcome, instead of every challenge being a binary success or failure (which I’ve seen in published adventures).

I’ve used skill challenges in 5e, but the main problem has been setting the DCs in order to achieve the desired difficulty. I have absolutely no clue how difficult it is to succeed on four DC 15 checks vs six DC 12 checks, as an example.
The main problems I had with skill challenges, at least the way they were run was that you had to have X successes before Y failures. So it didn't matter if the first thing you did should have solved the problem, you still had to pass the rest. It became a game of "who's got the highest ability for the next skill" because it didn't really matter what you did, it ultimately came down to did the player roll good enough to beat the DC. Did that happen X times before you failed Y times? Creative solutions, by and large, were not allowed.

Maybe you had a way of doing it better, and in my home game I pretty much ignored them after a while, but that's the way they were used in practice.
 

The main problems I had with skill challenges, at least the way they were run was that you had to have X successes before Y failures. So it didn't matter if the first thing you did should have solved the problem, you still had to pass the rest. It became a game of "who's got the highest ability for the next skill" because it didn't really matter what you did, it ultimately came down to did the player roll good enough to beat the DC. Did that happen X times before you failed Y times? Creative solutions, by and large, were not allowed.

Maybe you had a way of doing it better, and in my home game I pretty much ignored them after a while, but that's the way they were used in practice.
The main problems I had with D&D combat, at least the way that they were run, is that you had to hit the dragon X times before it did Y damage to you.

It didn't matter if the first thing you did should have killed the dragon, you still had to keep hitting it until it ran out of HP.

It becomes a game of "who has the highest damage output" because it didn't really matter how you attacked, ultimately it came down to did the player roll high enough to beat the AC and was the damage of the attack large enough.

Creative solutions, by and large, are not allowed.

(Skill challenges are dragons, where each hit does 1 damage, and they have only a few HP. Just like the DM is in charge of narrating "the sword blow didn't kill the dragon", in a skill challenge the DM is in charge of narrating why the one action didn't solve the problem.

There is no DC to cut the dragon's head off in 1 blow.)
 
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The main problems I had with skill challenges, at least the way they were run was that you had to have X successes before Y failures. So it didn't matter if the first thing you did should have solved the problem, you still had to pass the rest. It became a game of "who's got the highest ability for the next skill" because it didn't really matter what you did, it ultimately came down to did the player roll good enough to beat the DC. Did that happen X times before you failed Y times? Creative solutions, by and large, were not allowed.

Maybe you had a way of doing it better, and in my home game I pretty much ignored them after a while, but that's the way they were used in practice.
I see that as poor framing of a challenge. If the challenge is something you can overcome with just, say, convincing a single person, it probably shouldn't even be a skill challenge. Not all skill checks are supposed to be part of a skill challenge, and Rules Compendium has examples of skills in play where skill challenges are not involved. I do know what you're talking about, and the issue is using a skill challenge where one doesn't need to be added. Or sometimes players come up with a very creative solution and you just bypass the skill challenge, the same way you would let them bypass a fight thanks to a particularly creative idea. If the skill challenge was intended to be long, like 8 or more successes, and the players still came up with something that bypasses the entire thing, then that would just be bad framing (like requiring 8 successes to get through the gates of a city).
 


Whenever the 4e skill challenge rules are discussed, there’s often a lot of misremembered stuff tossed around. The rules don’t prescribe a certain order for the checks, for example, or that everyone has to roll. One player once told me that they didn’t like the rules—yet turns out the player had actually never even read them! Here are the basics of skill challenges from the 4e Rules Compendium:

There’s also advice on allowing suitable powers or rituals to count as successes, and the rules encourage the DM to include a variety of different skills and approaches. They talk about degrees of success, meaning that a good challenge takes into account the number of failures and successes to determine the final outcome, instead of every challenge being a binary success or failure (which I’ve seen in published adventures).

I’ve used skill challenges in 5e, but the main problem has been setting the DCs in order to achieve the desired difficulty. I have absolutely no clue how difficult it is to succeed on four DC 15 checks vs six DC 12 checks, as an example.
The problem is, a lot of people don’t really read the rules, at least not in their entirety. They read the parts they think are important or interesting, they skim parts they think they mostly “get”, they skip parts they get bored reading, and they fill in the gaps with past experience playing other editions or in other DMs games. What people remember about Skill Challenges isn’t the rules for running them, it’s how they were presented in the modules they ran, and how DMs they played with ran them. And as I said before, while the rules didn’t do a great job of explaining skill challenges, the skill challenges that showed up in modules were absolutely terrible.
 
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The main problems I had with D&D combat, at least the way that they were run, is that you had to hit the dragon X times before it did Y damage to you.

It didn't matter if the first thing you did should have killed the dragon, you still had to keep hitting it until it ran out of HP.

It becomes a game of "who has the highest damage output" because it didn't really matter how you attacked, ultimately it came down to did the player roll high enough to beat the AC and was the damage of the attack large enough.

Creative solutions, by and large, are not allowed.

(Skill challenges are dragons, where each hit does 1 damage, and they have only a few HP. Just like the DM is in charge of narrating "the sword blow didn't kill the dragon", in a skill challenge the DM is in charge of narrating why the one action didn't solve the problem.

There is no DC to cut the dragon's head off in 1 blow.)
I mean, if the "first thing you do" is collapse the Dragon's lair on top of the Dragon (and that Dragon doesn't have the ability to burrow), or the first thing you do is bribe/con/convince a much older Dragon to fight your target so that you don't have to, the entire fight is obviated. In that way fights can often be avoided more easily than a skill challenge, particularly if the skill challenge wasn't telegraphed ahead of time in the same way big fights often are.
 

The main problems I had with skill challenges, at least the way they were run was that you had to have X successes before Y failures. So it didn't matter if the first thing you did should have solved the problem, you still had to pass the rest. It became a game of "who's got the highest ability for the next skill" because it didn't really matter what you did, it ultimately came down to did the player roll good enough to beat the DC. Did that happen X times before you failed Y times? Creative solutions, by and large, were not allowed.

Maybe you had a way of doing it better, and in my home game I pretty much ignored them after a while, but that's the way they were used in practice.
I’ll agree that in practice skill challenges were often run this way. The DM would present an obstacle, a player would suggest a creative solution, the DM would call for a check and make a note of the result behind the screen, then ask the next player “ok, what do you do?” And you’d just have to sit there and wonder why the heck your solution didn’t seem to do anything, while the other players take turns sheepishly asking to make checks with their best skills until eventually the DM announced that you’d won or lost the challenge.

The solution here is to make skill challenges a dynamically evolving series of obstacles. It shouldn’t be one thing you need X successes before Y failures to complete, it should be a whole encounter, which changes in response to your actions, and is fully resolved after X successes or Y failures. When the player suggests a creative solution to an obstacle, you narrate their success (or failure) and then present a new obstacle. Like Moves in a PbtA game.

But, yeah, most modules weren’t written that way, and most DMs didn’t run them that way.
 

The biggest thing IMO is to actually call for a roll. Without a roll, no tension... And a lot of people seem to want to play 5E without asking for skill checks. 🤷‍♂️ It might not be "interesting", but it makes it actually a challenge.

When it comes to exploration and social challenges, removing the roll basically just makes it story-telling. Yet more people want ways to make these things challenging... shrug
While I don't necessarily think that a roll is required, calling for an ACTION is certainly required. It's actions that have consequences--rolls simply inject extra uncertainty. Players often avoid making hard decisions, because hard decisions mean taking some action, and thus consequences. Rolling is just one subset of actions.

The main problems I had with skill challenges, at least the way they were run was that you had to have X successes before Y failures. So it didn't matter if the first thing you did should have solved the problem, you still had to pass the rest. It became a game of "who's got the highest ability for the next skill" because it didn't really matter what you did, it ultimately came down to did the player roll good enough to beat the DC. Did that happen X times before you failed Y times? Creative solutions, by and large, were not allowed.

Maybe you had a way of doing it better, and in my home game I pretty much ignored them after a while, but that's the way they were used in practice.
Anything that can be solved that easily should not be a skill challenge. Literally exactly the same as "anything that can be resolved in a single act shouldn't be a combat," or "anything that can be resolved in a single act shouldn't be an adventure."

Now, no DM is perfect (I certainly am not!), so it's quite possible for any of the above things to happen in actual play. You didn't see the one-action resolution for something ahead of time. There are AFAIK only two valid responses to that:
1. Level with your players. "Hey guys. I goofed, I didn't think of that as a solution. I'd really like to proceed with things as I had originally planned. You totally outwitted me, so props for that, but can we skip this obvious solution and go through this as I'd planned?"
2. Accept it. "Wow, alright, you guys totally solved that immediately, here's your XP."

No rules--whether for SCs, combats, adventures, campaigns, whatever--have ever said you should enforce continuing on if it doesn't make sense. That people cut slack for all sorts of older-school rules that run into problems like this, but don't for something like Skill Challenges, continually upsets me.

The solution here is to make skill challenges a dynamically evolving series of obstacles. It shouldn’t be one thing you need X successes before Y failures to complete, it should be a whole encounter, which changes in response to your actions, and is fully resolved after X successes or Y failures. When the player suggests a creative solution to an obstacle, you narrate their success (or failure) and then present a new obstacle. Like Moves in a PbtA game.
Absolutely, 110%. Each action should change the state of play, just like in combat.

But, yeah, most modules weren’t written that way, and most DMs didn’t run them that way.
Sadly...this is also 110% true. The modules were terrible, and while the actual rules were reasonable and not as badly-written as I had originally thought, the vast majority of DMs ran them in the worst possible ways. Dry, static, bullheaded, utterly mechanistic, and purely down to "which threshhold do you pass first." Nothing like what they should be.

As I've said in other threads: if many people used Reaction rolls (just as an example) incorrectly, that doesn't mean Reaction rolls are a bad mechanic. But, just like many other parts of 4e, people often had an initial antagonistic reaction, and interpreted absolutely everything as though it had to be perfectly micron-precision mechanistic at absolutely every level of play....sucking the fun out of the game purely in how they chose to play it, making it "MMO-like."
 

By the time the Rules Compendium was published, D&D 4e skill challenge design was finally sorted out in my view. Anything published prior to that point can effectively be ignored. At the time, I had a serious math guy in my group who crunched the numbers on the RC version and it was very solid, provided the challenge was run with the characters in initiative. As long as the group was able to think of initiative in a way that didn't conjure combat-like play, it really presented a solid challenge that produced a fun story. The running joke in my group at the time was that skill challenges were actually scarier than combats. In fact, including them as designed in my games pushed players from being specialists in skills to more generalists and encouraged them to take skill powers or utility powers that were often ignored by the character optimization threads of the time. They went from being geared mostly toward combats to having a mix of options for social and exploration. This was a good result in my opinion.

I don't really think this same structure can be imported directly to D&D 5e. It just doesn't fit the paradigm in my view and the math is very probably off for the latest edition. I do still recommend having some kind of structure for exploration and social interaction challenges though rather than just run them on the fly. For D&D 5e, in my games that means thinking about specific obstacles/complications (for exploration) or questions/objections (for social interaction) that may arise during the course of the challenge, then not thinking about the solutions. Difficulty is set by way of the number of obstacles/complications or questions/objections - the more there are, the harder it is. Once we go through all of them, I tally the number of successes and determine the result which is typically a set number of successes for overall success with anything less than that being overall failure or progress combined with a setback.

When it comes to social interaction challenges specifically, the structure I use is very much based on the DMG's rules for social interaction challenges which I think work well enough for this edition of the game. In this case, each overcome objection works toward modifying the NPC's attitude toward the PCs temporarily, setting them up for the final ask which determines if the PCs get what they want or not. Because this structure incentivizes trying to learn the NPC's agenda, bonds, ideals, and flaws (and in the case of my games, any relevant history), this means that more than just the party's face can interact in a meaningful way to support the more Charisma-based characters. It works well and is worth considering in my view.
 

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