Like many people, I’m curious about what AIs like ChatGPT and Claude can do. So I asked an AI to play Dungeons & Dragons with me. A game that alternates between prose/improvisation and numeric, turn-based play seemed like it would exercise the whole gamut of AI’s capabilities.
The TLDR: it’s fun, but you have to work at keeping the storyline moving. Along the way you get fascinating glimpses at what AI does well, what it does poorly—and how worried you should be about it taking your job!
As an aside: I wanted to support human creators during this experiment. After all, humans wrote epic fantasy novels, which inspired other humans to build a game, which in turn created a worldwide, multi-generational community of players and more creators. Throughout this post I’ll mention some fun items I purchased.
What Is the AI Bad At?
I bet this is what you want to hear first. 🙂 Generally, it has a hard time with:
- The details
- The big picture
- Space
- Time
More about all that shortly. Backing up: I started this experiment barely remembering anything about D&D. I chose to play a druid because of a flowchart I saw on the Internet:

The AI said, I’ll give your druid a forest adventure with forgotten stone circles and such. I asked for a party and the AI said, meet Kara the fighter, Rurik the cleric, and Nym the wizard. Off we went into the forest, rolling Survival checks, and soon encountered a torn piece of cloak that made us choose: continue along our planned path? or divert to investigate whether someone needs rescuing?
Without rehashing the whole thing, the AI spun a tale of outsiders (“they smelled of dry earth and iron”) who brought a Blight to the forest and devolved the local druids into Wretches. It was mildly repetitive—there was always a tunnel, that led to a chamber, that had a dais, where you had to do some tasks in order, which opened a door—and after defeating the Blight there was also a weird shard that had to be destroyed for no clear reason.
At this point I had a better idea of how the AI was working. I bought the Player’s Handbook and some solo adventures from Toronto-based Obvious Mimic Press to get better acquainted with the rules, and started a second adventure.



An Improvisation Machine
Large Language Models are essentially improvisation machines. They take the conversation so far as input, and output text that could plausibly come next. That means that, when acting as a Dungeon Master, they don’t have the storyline planned out in advance.
I started thinking of the AI as a TV writer who doesn’t know if they’re getting one season or ten. It throws mysterious things at me with a vague expectation that it can tie it all together eventually. My job as the player is to watch for a few threads that gel and make me go “ooh, that’s a compelling plot.” Then I focus on those threads and the AI will pivot along with me.
For the second adventure, the AI took us to a superstitious logging town on the edge of the forest.
The buildings are low and dense, with roofs of tarnished tin and mossy slate. The air smells faintly of iron filings and burning pine. Wind howls through the crooked alleys like a warning whispered too late.
In the center of town stands a massive metal box, three stories tall. No-one looks at it.
A coal-smeared girl watches you, holding a wooden doll whose limbs bend the wrong way. A pair of men drag a bundle wrapped in canvas. You hear faint, rhythmic ticking from within the bundle.
The guard jerks a thumb over his shoulder toward the town. “Go on then. Head to the Snoring Ember. Don’t wander after dark. Don’t touch anything that hums. And if you hear singing coming from the smokehouse, you didn’t.”
As you can see, the AI’s real strength is in atmospheric description. The game moved more briskly when I didn’t passively let the AI “lead” but instead picked out details and pursued them. The innkeeper gave us keys 3, 4, 5, and 7… the identity of the guest in room 6 became a plot point. A non-player-character made some contradictory statements… he turned out to be a villain. Overall the AI delivered a genuinely creepy “clockpunk horror in a frontier town” story.
I purchased the Creature Codex and Tome of Beasts 1 from Kobold Press, since they seemed likely inspirations for the monsters.


Limitations
I mentioned the AI had trouble with the details, the big picture, space, and time. Some examples:
The details: it regularly changes my wizard from she to he; forgets whether my cleric has a mace, morningstar, or hammer; says the magic item is onyx, then brass. When the characters reconvene at the tavern after doing separate investigations, the AI has them deliver a “summary” that doesn’t match the day’s events at all.
The big picture: it launches into an epilogue when the antagonist hasn’t been faced yet; it frequently veers wildly off-theme (e.g. presenting a puzzle room filled with music boxes in an adventure where the foes are not in the least bit whimsical).
Space: it says the portal is floating in the middle of the room, then on the far wall; it describes locations as miles apart yet connected by a short tunnel; it can’t keep track of who is in melee range with who during a fight.
Time: it regularly mixes up whose turn is next in initiative order; forgets which opponents are already defeated in a fight; and has characters you left behind several scenes ago suddenly contribute dialogue.
These limitations shouldn’t surprise us. LLMs seem to understand that objects exist in space and events occur through time because they have been trained on mountains of text written by humans who understand those things. But scratch the surface and it’s clear there’s nothing underneath that is keeping a map or timeline of the game at hand.
The AI tried to fill in one-liners during combat. They were so cringey I begged it to stop. A sampling of its taunts while fighting Stone Cursed:
“Let’s see if you crack like the statues you look like.”
“You were empty inside. Now you’re just… empty.” (just plain zero?)
“You like stone? Let’s see how you handle living stone.” (before striking with a wooden staff… what?)
It also came out with some pretty weird similes:
“blunted like a blade in the rain” (what’s that blade made of, soap?)
“screams like a bowstring snapping” (pretty sure snaps and screams are different sounds)
“the green glow in his eyes flickering like wind through leaves” (sunlight through leaves, maybe?)
Tips For a Fun Game
If you decide to try a similar experiment, know that—unfortunately—you will have to do the bookkeeping! Keep track of how much damage you have done to the opponent and mention it often during combat in case the AI forgets. Correct the AI if it mixes up initiative order, says the opponent hits with a roll below your armor class, forgets that you have imposed Disadvantage on the opponent, etc.
AIs try to be helpful. In a D&D context that means it tends to let your crazy plans always work. So challenge your character when the AI won’t. Give that poor schmuck who’s about to walk into your ambush a chance at passive perception. Ask if you need an Acrobatics check to avoid falling out of the rafters where you’re spying. Insist that the shadowy envoy from the Thieves’ Guild demand something in return before cheerfully telling you everything he knows.
AIs also try to keep you talking: like social media apps that invite endless scrolling, AIs end each interaction by suggesting what you could ask next. In a D&D context that meant it constantly encouraged me to “explore” or “investigate” or “do a deeper analysis”. So explore if you feel like it, but push ahead to the next scene when you’re ready. And when enough pieces are in place for an endgame, just have your character yell “The time is upon us! Tonight we ride!!” and the AI will take the hint. 🙂
AI is improving quickly, so the next generation of models may overcome the faults I described above. I guess I will find out if these four venture into the forest again!






























