The Challenge of High Level Adventures in 5e D&D

My D&D friends and I have known each other for a long time. Two I’ve known since grade school, another three since Jr. High School. Even the newest to the group is a friend of many years. And in that time, we’ve played a number of D&D and other tabletop games. But never to high levels… until now.

The game that I DM right now is a continuation of a previous adventure that went for two years. I run a game in a homebrew world I call “The World of Ebber” (see my D&D Content section if you care to learn more about that). I do not use or adapt boxed adventures, but rather come up with my own storyline, dungeons, maps, puzzles, etc. as we go. It’s rewarding, but a lot of work. The first story arc found the players pursuing an evil wizard across the continent as he attempted to free six demon lords, and eventually their master, Gag’drin, the most powerful demon to ever demon. We started at level 1, with the characters escaping from prison, and by the end of two years, they were level 11.

Now, when I started this world, I stated confidently that the players would be able to level all the way to level 20 in this world setting. That seemed realistic at the time, because I am terrible at math.

Let me explain.

5e D&D is a system that attempts to give the DM guidelines, such as challenge ratings, to make it easier to present appropriate challenges to players. The Challenge Rating (CR) is supposed to represent a challenge fit for a group of four at a level equal to the CR. So CR4 means a group of level 4 adventurers would find this monster challenging. Simple, right?

Now for starters, this is not very accurate. Players are going to do a lot more than just attack every turn, and in my experience as a DM, you better throw higher CRs at them or it’s all a cake walk. But, another important aspect of the CR system is experience given. The CR of the encounter (not always a battle, but c’mon, we all know players always resort to violence first) dictates experience given. This is where the system starts to suck at higher levels. Because, each character level (experience required to advance in power and skill) is based upon eight encounters at appropriate CR.

Encounters at early levels go pretty fast. The monsters rush in, the players do one or two rounds of battle. In those one or two rounds, some of the players might even fall, because hitpoints are low in the early levels. It’s all very exciting, high pay-off with low time commitment. You might get in a couple of battle encounters and a couple of non-battle-encounters in a single session, and your players are leveling maybe every other session. Life is good.

But, as the levels go up, so do the difficulties of the battles. Player powers become more extreme, and the DM has to deploy greater tactics to make things challenging. Everything has more hitpoints, so battles take longer. Unless everyone is super dedicated to making the rounds go quickly, a single round of combat can take a long time (this goes double for my group, which now has 7 players, all in various states of distraction or inebriation at any given moment).

So, two years of game-play to get to level 11 starts to make sense when you do the math. Each level takes exponentially longer to complete, because of experience given. If I really want my players to reach level 20 and then retire in glory, we’d be looking at probably another 4+ years of gaming. I used to hear stories from old-timers when I was a kid about their gaming group, and the characters they have been playing for a decade, and it sounded really awesome. Because I was a kid. As an adult, I don’t find that concept awesome. There are way too many options in the game to be stuck playing the same character for too long.

So what is the solution? I have decided to switch out the official experience system for narrative milestones. I created a very high-level outline of where I expect this adventure to go, and set milestone points within that outline for when I will grant my players their next level. I will no longer track experience at all. Whatever happens each session happens, and the reward of a new level will be given based upon narrative progress rather than number crunching. I will obviously adjust these milestones over time if things take an unexpected turn, but the general guideline is there.

I think this will be beneficial to everyone, given my goal of allowing the players to ascend to the highest character levels. Maybe that seems like a foolish goal to some DMs, because the fun is in the storytelling, and gaining new powers is only a minor part of that fun. And I could see that point of view. But, the game creators were nice enough to provide 20 levels of character skills, and I know my players love gaining new powers. We don’t necessarily have another four years to spend on this. So, I am at peace with the decision. Character levels will be more like they were at the earlier stages, with a gain every two or three sessions rather than two or three months.

Another aspect of high level characters that I had not really counted on is their survivability. Challenge levels of encounters does not really scale well in reality. I recently had my players face off against an adult green dragon. This is a CR15 monster, so according to the game designers, a single adult dragon should be a good challenge for a group of four level 15 players. Cue the laugh track on that one. At about 200 hitpoints in health, this thing can do a maximum of about 50-60 damage per round, including legendary actions. The players, unless they have already gone through a huge challenge to get there with no rests, will also be doing about that much damage per round. Doing some quick math here, that means the dragon lasts one pathetic round against a fully rested party.

So you see where this challenge rating thing gets pretty bad at higher levels. With battles taking so long, giving the players a challenge to get to the dragon with no rests would have taken days in itself, and if I add more creatures to the encounter to drive up the challenge and “action economy” (a great tactic with lower level adventures), I am making the dragon encounter more complicated and time-consuming.

So it becomes a balancing act of: do I want the players to spend several sessions fighting their way to this dragon? Do I want the players to spend several sessions actually battling this dragon? In my case, the answer to both of those was a resounding NO. I want to get through some story each session (about 4 hours), not spend forever on a single encounter.

What I am finding myself doing is reworking the stats of monsters to actually be a challenge for the characters. For this dragon, for example, I increased all of its base attacks to about double what they were, and its breath weapon was somewhat increased as well. Im also doing hitpoints for some pivotal monster encounters, like this one, on a more narrative basis. I gave it about 600 hitpoints in the first place, but if that doesn’t seem to be a good challenge, I… fudge it (I don’t tell the players, of course). The goal is to have a difficult encounter that feels like the players just managed to pull it out, but they could have died. And since I am doing milestones for levels, I don’t have to worry about the CR adjustments when I alter monster stats.

So, that’s my plan for managing a high level 5e adventure, from level 11-20. Part of me rails against these ideas, because it breaks the official rules and “cheapens” the level gain. But in the end, I and my players are in it to have a fun time, and I think this will provide that experience.

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