Using D&D 4E’s Skill Challenges in 5E

I just ran across another blog post about utilizing D&D 4th Edition’s skill challenges within D&D 5th Edition.  This really struck a chord with me, as I had just tried doing this in my last D&D session, running a conversion of 4E’s Remains of the Empire (found in Dungeon Magazine #165).  This module has multiple skill challenges in it, and they seemed like they could be really fun to incorporate into our game.

I really wanted to utilize more roleplaying in our game.  Get the players into character more.  And have them pass challenges for XP without resorting to combat every time.

Unfortunately, utilizing the skill challenges didn’t go as planned.  My players grew confused and frustrated when good skill rolls failed to pass a challenge.  They didn’t understand that they needed multiple successes to pass a challenge, which is completely out of the norm for 5E.

This is my own fault.  And I want to take this opportunity to present a few thoughts to other DMs on how to make these run more smoothly.

In 4th Edition, skill challenges required players to roleplay through a situation and utilize one or more skills to talk their way through a challenge.  This could be persuading someone to your way of thinking, talking your way past the guards, or convincing someone they were being used by the bad guy.  In any case, they required a number of successes during the encounter before the players rolled three failures.  The harder the challenge, the more successes were needed to pass the challenge.  So, for an easier challenge, you may only need three successes to pass before you got three failures.  For a hard challenge, you may need six or more successes to pass.

The first thing you should do is explain to your players what skill challenges are and that you plan to incorporate them into your campaign.  This is probably the biggest, most important thing you need to do as a DM.  If your group has only played 3.5E or 5E, or anything but 4E for that matter, they’ve never encountered these types of challenges.  They won’t know what they are or how to handle them properly. And if you don’t explain to them your plan, they’ll end up like my players: frustrated and confused.  Make sure you explain that they’ll need more than one good roll to pass the challenges, and that a single failure on the die doesn’t mean they failed the challenge.

Next, you need to indicate to your players when they’ve come upon a skill challenge.  This isn’t jumping a gap or climbing a hill, this is a roleplaying encounter.  And conversations can have multiple opportunities of back-and-forth discussion to achieve the desired outcome.  So, make sure you let them know, either by hinting or by just outright telling them they’ve hit a skill challenge, or they may miss what the encounter is about.

Lastly, make sure you drop hints or clues as to their success rate during the challenge.  They need to understand if they’re making progress or falling behind.  If they don’t see any progress, they’ll feel like they’ve just hit a brick wall.  An impossible encounter.  And when players feel like they’ve been stonewalled, the usual course of action is to initiate combat.  When all else fails, fight your way through, right?  So, make sure they have an idea of how close to success they are.  Or just let them know they can outright ask how they’re doing.

When you first run these, maybe make things more transparent.  Tell them it’s a skill challenge.  Let them know how they’re doing throughout the challenge.  That lets them get used to these types of encounters.  Once they can tell when you’re dropping these skill challenges on them, then you can drop them in-character or be more subtle about them.

So, hopefully that give you some ideas on how to incorporate these challenges into your 5E games and run them smoothly.  If you’ve run these or have anything to add, feel free to post in the comments below. I’d love to hear how you utilized these within 5th Edition and how they went.


One thought on “Using D&D 4E’s Skill Challenges in 5E

  1. I do skill challenges in 5e, but modified. I boil it down to giving the players a series of situations and then they do something and roll a check and we go from there. To me, the most important thing is to make sure you have planned out what happens if they succeed on every check, and what happens if they fail on every check. Sometimes the fails lead to hilarious stuff. To me the best thing to do with skill challenges is a montage – either a travel montage or a “fixing up the vehicle” montage complete with a slow motion high five at the end.


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