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Nerdarchy > Dungeons & Dragons  > D&D Ideas — Challenge
5E D&D challenge dm tips

D&D Ideas — Challenge

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Welcome once again to the weekly Nerdarchy Newsletter. This week’s topic is challenge, which we discussed in our exclusive Patreon live chat. We hangout every Monday evening at 8 p.m. EST with Patreon supporters and talk about D&D, RPGs, gaming, life and whatever nerdy stuff comes up. You can get the Nerdarchy Newsletter delivered to your inbox each week, along with updates and info on how to game with Nerdarchy, by signing up here. The Out of the Box: Encounters for Fifth Edition Pledge Manager remains open, but only for a short time. Production on the book continues smoothly and we’re giving it an additional level of editing while the few remaining pieces of incredible art from Kim Van Deun and maps from Darryl T. Jones come. Speaking of challenge, in All That Remains adventurers are faced with the worst kind of challenge — deciding between treasure and monster fighting! Check out the Pledge Manager here.

5E D&D challenge dm tips

Recent videos

Delving Dave’s Dungeon

Challenges in fifth edition Dungeons & Dragons or any roleplaying game can mean a lot of different things. In D&D challenge could literally just be the measurement we use for determining the difficulty of an encounter. Or we could be talking about Skill Challenges from fourth edition D&D.

Both of these are mechanical parts of the game. What about challenging the players via roleplaying or intellectually? An intense roleplaying encounter might be super draining emotionally on players and challenge them in ways you haven’t thought of as a Dungeon Master.

Let’s create a challenge. Puzzles and riddles are intellectual challenges that can be problematic and fun at the same time. Usually the problem is they are designed to challenge the player and not the character. Often this means they might not make sense for certain characters to solve them.

We handle this at our table by using the collective intelligence of the group to represent the smartest characters in the party.

Three Doors, Three Beasts, Three Aspects

First door is carved with a fearsome dragon (Greed)Second door is carved with a beautiful unicorn (Purity)Third door is carved with a stoic wolf (Loyalty)When a character steps before a door the creature demands they define it. If they don’t respond they are attacked by the creature. If they give an incorrect answer they are attacked by the creature.

  • Dragon breathes fire (Dexterity saving throw)
  • Unicorn head charges and stabs (Attack roll)
  • Wolf leaps forth to savage them with it’s maw (Attack roll)

Use the 5E D&D Dungeon Master’s Guide chapter 5 — damage by level, under the traps section. The first player to give a correct answer at a particular door receives a boon.

Boon Suggestions
  • Dragon. Spits out coins or a gems, grants resistance to an element (temporary or permanent), gives the character 1-3 Legendary Resistance and once they are used they are gone
  • Unicorn. Grants the effect of bless spell for 24 hours on the person plus two creatures of their choice, resistance to poison (temporary/permanent), grants the character one use of the teleportation spell
  • Wolf. Grant Pack Tactics for 24 hours, increase movement by 10 feet (temporary/permanent), gain a wolf or dire wolf companion that is loyal to the character for 1 week
  • Any. Increase an ability score by 1 or 2 points that would correspond with the creature

From Ted’s Head

When it comes to fifth edition Dungeons & Dragons or really any roleplaying game, challenges can be just about anything. So I am going to break my ideas down into three different tips.

Challenge rating

Over the last few editions D&D has had a challenge rating for monsters. On occasion the rating system is a challenge in and of itself in how accurate it can be. But there are typical takeaways. In 5E D&D using the challenge rating equal to the party level has a chance at the low levels to drop a party member if the dice go in the favor of the Dungeon Master. Once you get to second and third tiers there is a little more wiggle room and more powers to get your fellow adventurers back up.

Challenges are also a way of doing skill tests or skill challenges, a great way to bring skills into the game. When doing these be fluid and allow options that players describe if they make sense. Allow the players offer creative ideas to add to the event and skill challenge. Set this up with the need for so many successes before you reach so many failures. As the DM you can have the challenge as either win or lose or somewhere in the middle depending on the challenge.

Another thing when it comes to the word challenge is taking the challenge and getting behind that DM screen for the first time. It can be intimidating and for sure is a challenge, but for the most part you are probably gaming with friends. Even if you do a bad job you are giving the regular DM a night off and giving them a chance to play instead. But chances are you will have fun and see a whole new side of this game you had not considered before. I am not going to strong arm you into the seat. I am not going to try any pressure sales tactics but allow me to share with you my story.

I started playing when I was a teenager. At first I really did not understand all the rules and some of the game was a collaborative storytelling without any real risk of death. My main character was 20th level in multiple classes and I can recall him being a DM PC during one dungeon solely so he could collect items from the fallen monsters. The usual DM gave us these arrows that if we collected dragon blood they could do some cool stuff. So I filled a hallway with dragons and loosed the party on them. There were no silly attack rolls, the players just narrated how they killed the dragons. It was pretty stupid, but I was a teenager and the players were happy being in a dungeon fighting dragons, while my character wandered behind collecting the blood he wanted.

The cooperative angle of that game might have been ahead of its time, but there was no challenge to the session. As I got older I learned more. I gamed with different groups, each with a slightly different playstyle. I had the antagonistic DM. I played a game with only three players where part of the game was player vs. player with one of the three keeping us all alive. I occasionally wonder how that game would go these days.

When I am the GM I want the players to succeed, and when things work perfectly, they do so just barely. A hard won fight is the best. Those stories become memorable. But that challenge is hard to set up. I have had to have monsters surrender well before they would and I have had monsters offer up a chance for the players to surrender, so that I did not kill them all. All because the dice offer an unknown element of the game. If the dice are with the DM and not with the players big swing and a TPK can happen. If it goes the other way the villain is wiped off the mat and the party just moves on.

Stepping behind the GM screen offers many different challenges, true, but the rewards it offers are off the charts. I have always been a creative person. I like coming up with stories. As a GM I get to see these things unfold while being in the presence of friends and people I care about. We get to have these shared experiences, because one person said, “I will run a game.”

For every GM that has said this for you, if you have not stepped behind the GM screen consider giving it a shot. I issue that challenge to you. You can use prepared material, in full, in part or not at all. You can over prep, under prep or prep not at all. Whatever you feel comfortable with just give it a shot once.

I am so glad after some horrible sessions in my past that Dave and Steve, the original GMs I started gaming with back all those years ago, pressured me into stepping behind the screen. Yeah, I’ve made mistakes. I am confident I will make more as I have a long road ahead. But every game I run, every new player at the table and all of my experiences equip me for the challenge of being able to step behind the screen and have fun.

Give it some thought and see if it is something you can do. Start a session zero to see the kind of things people want to do and have fun. After all, I have said this before, roleplaying games are nothing more than playing make believe with rules. At its very heart and core it is about fun and imagination. Enjoy!

From the Nerditor’s desk

Nerdarchists Dave and Ted presented a puzzle challenge and a personal challenge respectively, and now I feel compelled to approach this topic with alliteration in mind.

A DM spends most of their time between and during sessions creating and presenting challenging situations to players and their characters with monsters, mysteries and menace. So I’m doubling up on the alliteration and doubling down with player perspective and a challenge for the people on the other side of the DM screen.

At your next D&D game challenge yourself. Head into the game session with a clear goal you aim to accomplish. Your DM might be the one throwing terrible monsters and perilous dungeons in your path and part of creating the shared experience is what you bring to the table too.

Every time I sit down to roll funny shaped dice there’s something I hope to achieve and for me this always results in a more engaging game. I’ll give you some examples of player challenges you can try in your games. And I’ll make it a list of 12 so you can show the d12 some love and roll on the list if you’re so inclined.

  1. Use each of your class features at least once
  2. Support an ally with a buff spell, feature or Help action
  3. Use your tool proficiency
  4. Use a racial feature
  5. Use a language you know other than Common
  6. Make another character look good
  7. Workshop a character catchphrase
  8. Talk your way out of a fight
  9. Talk your way into a fight
  10. Reveal a secret about your character to the party
  11. Do the opposite of the expected or what you’d normally do
  12. Do something in secret without the party knowing

Any of the challenges I take on as a player are meant to affect the storytelling in a meaningful way. In a lot of cases, especially in one shot games or Adventurers League games with unfamiliar players, my challenge is to engage with the other players. One of the best ways I’ve found to do this is supporting their character during the adventure.

Casting enhance ability or even just using Help during a combat creates a connection between characters. Players dig it too! They get a better chance to do their cool thing. But you can support other characters through roleplaying too. It’s as easy as showing interest when a player describes their character, or tells the group something about their backstory or whatever. Stories and bonds deepen when characters become more real than the numbers on the character sheet.

Challenges involving character features enhance stories too. Let’s say your character is proficient with weaver’s tools. The party finds a storage room where all the cultist robes are kept (there’s one in every cultist base). All of a sudden the party decides to track down the robe manufacturer your character knows by the distinctive sewing pattern of the hem. Storytelling!

At the end of the day a challenge is a call to take part in a contest or competition, and by this definition players create our own challenges all the time. A different kind of challenge asks players to come to the table with a fresh perspective. Challenge yourself to strengthen the connections between characters and players, and use your character’s features in new ways (or even at all) and after a while these things won’t be much of a challenge for you at all.


D&D Monsters Witchery Style Video Inspired by Zee Bashew

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