I'm always disappointed when I sit down in a new game on Roll20 with my characters who are built to be good at combat and at skill challenges only to see that the DM doesn't use skill challenges or doesn't run them properly. Some of the best feedback I get on my games is from the skill challenges, so I'm going to show you how to run them. 1. Read the D&D Essentials Rules Compendium , pages 157 to 163. Seriously, this (and this guide, hehe) is all you want to read on skill challenges. Ignore and forget everything else, including everything you've already learned or think you've learned. If a skill challenges comes out of the DMG1, DMG2, or any pre-RC module, recognize it as flawed and rewrite or cut it. For reference, the updated DCs for skill checks are on page 126. Don't be a biased DM and make up DCs based on your whim or how "creative" your players are. Just use that chart. (Or this handy one , if you like.) 2. Recognize that skill challenges are a pacing mechanic for non-tactical situations just like hit points are a pacing mechanic for tactical combat. To be fair, DMs have been running "skill challenges" for years. Situations come up in game, dice come into play, and you state actions and make a few checks until the DM is satisfied that you pulled something off or totally blew it. Of course, this is mostly just based on DM bias. Skill challenge mechanics offer you a way to take that bias out of the equation by providing DCs, primary and secondary skills, and advantages to create a consistent framework that is fair and balanced. It also gives you a means of pacing these scenes so they aren't so short as to be trivial, nor so long that they're tedious. Mechanically, they represent equivalent challenges to X number of standard monsters where X is the skill challenge's complexity. 3. Understand that skill challenges are based upon the fundamental conversation of RPGs : GM : What do you want to do? Player : I want to do X. GM : When you try to do that, this happens. What do you want to do? Throw in some skill checks and repeat. Key point here: Give the characters something to react to. If you give them nothing to react to, the players will look at their sheet, find their highest skill, suggest a complication to overcome based on that skill and ask to make a roll. This isn't ideal in many cases and can lead to the "hilarity" of "Intimidating the grass." While it's perfectly okay for players to suggest complications to overcome, don't state the goal of the skill challenge and then abdicate the rest of your role. Just like with monsters in combat, use complications to get up in the characters' grills. Give them something to react to, something that stands in the way of their goals, something interesting that demands their attention, right now. In a skill challenge, there is an overarching goal, a complex activity. It might be making your way through the Fetid Swamp before the goblin horde catches up to you. Or convincing the council of nobles to back your play against Duke Badguy. Or solving a riddle to end the ritual before the Gates of Hell swallow the world. Or anything that can't be handled in a single skill check, really. While the PCs are pursuing the successful completion of this activity, you're throwing complications at them, say, Acid Quagmire, Hidden Allegiances, or Infernal Glyphs, respectively. If the skill challenge requires 8 successes to beat it, then you should have 8 complications to throw at the PCs. Improvise them or come up with a list that will help you prepare to improvise using fictional "tags" like I've just given you. (Yes, the players can suggest their own to overcome.) Frame the scene and ask "What do you do?" Here's what it looks like in play (though I'm keeping the prose simple): DM: You're being pursued by the goblin horde through the Fetid Swamp. Along the way, you encounter great fields of steaming mud mixed with the acidic secretions of the foul denizens of this swamp. They block your path and slow you down. How do you deal with that? Player: I lead the way for the party and climb a tree and use the vines to swing across this area as quickly as possible. DM: Great, sounds like either an Acrobatics or Athletics check? The DC for this complication is moderate. Player: *rolls Athletics* Nailed it. I lead the party through the vines and over the acidic quagmire. Player 2: Let's see the horde keep up with that! DM: Nice. Once past the acidic quagmire, Player 2, you stand at the edge of a vast lake. Ominous swirls in the water alert you to lurking predators. The swim's easy enough if you aren't savaged by whatever is in the water. What do you want to do about that? And so on until the PCs win or lose the skill challenge. Everyone takes a turn in whatever order makes sense since the whole party is involved in the complex activity, generally. (I like initiative order myself.) Complications that are resolved go away; those that aren't resolved either stay in play or change according to context. When you're not presenting and resolving complications, you should be fostering interaction between the PCs and each other or with NPCs in the scene. Ask a lot of questions and look for things to reincorporate into your descriptions or to heighten the drama as you describe new complications. 4. Success is "Yes, and..." while failure is "Yes, but..." Here, "Yes" refers to the goal of the skill challenge, whatever it is. Continuing with the Fetid Swamp example, the goal is to get through the swamp before the goblin horde catches up. If the PCs manage to succeed in the skill challenge, yes , they outpace the horde and get away unscathed. If the PCs fail the skill challenge, yes , they outpace the horde, but they incur a cost or additional complication that carries forward. The key takeaway here is that failure cannot be a dead end. The adventure must move forward. It's possible that moving the adventure forward might include the possibility of being caught by the horde; however, these things need to be examined on a case-by-case basis and collaboration with the players is encourages so that everyone agrees on the stakes to be played for in a given skill challenge before it is kicked off. Failure needs to be interesting and allow the game to move forward, always. That's the basic gist of skill challenges, or at least the bits I find DMs are missing. I hope this helps and welcome any questions or comments. If there is interest, I can post a few examples of skill challenges I've helped other DMs write so you can check out the format I use.