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Overthinking It

by Jae

As a DM you will run into a lot of problems when running D&D. While most of these problems can be solved with knowledge of the rules or simply talking through an issue with your players, there is one  problem that is hard to manage without breaking the flow of the game. We’re talking about player overthink.

If you’re a seasoned DM you’ve seen it before. You set up a simple puzzle with no tricks, just very straightforward. Yet your players sit and ponder for ages. You always have the option of simply telling them they are overthinking things, but that really takes the wind out of their sails. Not only do you run the risk of making your players feel stupid, you break the game state by giving them direct information on how they should proceed. Sometimes you can’t get around this, but there are a few tricks to help avoid overthink in your games.


It may sound counter-intuitive, but adding complexity can help avoid overthinking. The easier a puzzle is or the more obvious the trap, the more likely the players are to overthink them. This can be seen with one of the easiest traps in the world: the simple pit. The main value of the simple pit trap is that it is simple. Countless players have tried to rig up complicated rope systems to get over what is essentially a large hole they could have easily jumped across.

If you increase the complexity of the trap, players will look at it differently. If it’s too easy, they will think the ease of the trap is part of the trap and there is something more difficult looming out of sight. Putting thought into a complex trap will allow them to accept that they found the answer. This paradox is generally caused by veteran player expectations. It’s a “once bitten, twice shy” phenomena.

When a player encounters a trap or a puzzle of any kind, they have certain expectations built in their minds. It’s good to defy expectations from time to time, but it’s also important to live up to them. The first expectation players have for any puzzle, regardless of if it’s new to them or not, is that it is a trap with some sort of drawback.

This is seen more in people who have a background in playing D&D for a long time or have some pop culture knowledge of dungeons. They expect everything to be deadly. While it can be really satisfying as a DM to watch your players press a wrong button and tell them ”nothing happens,” it’s also not great for storytelling.

In addition to expected lethality, players need to be presented with some sort of challenge. This is not just something you can calibrate by level. A challenge is equal parts based on the players, as well as the characters they’re playing. A good example of this is putting real world puzzles, like a crossword or a Sudoku, into a dungeon. Players never overthink these extremely metagame puzzles because they know how to solve them.

To increase the challenge of a puzzle or trap you need to consider how your players might react. Place clues into your narration that they can uncover as they ask questions. This gives them some active challenge without changing the puzzle’s core mechanics in any way.

The Overly Cautious Player

Veteran players tend to develop a healthy but un-fun fear of puzzles and traps. This can lead to two outcomes that can become irritating for a DM. The first is that players shout “I check for traps!” in literally every room they walk into. The second is that players will spend too long debating the danger of a trap and take no actions.

If you’re a long time DM, you’ve probably seen players sit around a table and debate the best way to go about handling a puzzle they’ve already solved. The worst part is they have already figured it out, but often worry about the “what if we’re wrong?” scenarios for longer than it took them to come up with the solution. It’s good that players fear the consequences of their actions. But there are limits to everything in a game.

Luckily, there are a few good ways to combat the overly cautious player situation through gameplay. The first is to design a section of the adventure with a single puzzle in every dungeon or quest that is simple and straightforward. This will condition players not to overthink things without clear warning signs to do so.

If a puzzle looks relatively harmless, make sure it is. If a puzzle is supposed to be deadly, show the players this with the bones of fallen adventures or blood stains on the walls nearby. Good signaling goes a long way here. Proper narration gives subtle clues to your players without hitting them over the head that the situation is dangerous.

The second way to counter overthinking is the pressure of time. If you make players feel like they only have a certain amount of time to complete a task, the players often become more impulsive. This can add some tension to the story. Dynamic tension is important to maintaining a good game feel.

When adding a timed element to a story in any fashion, you can do so with room elements. A descending spiked ceiling, or a chase mechanic where a monster with a sack of gold has just dashed through the next door which is locked with your puzzle are a couple examples. Both of these add some stress and a bit of fun while keeping the players on their toes and feeling like real adventurers in a tough situation.

The last way you can curb this behavior is a dungeon or series of puzzles that penalize the players for overthinking. Design traps that can only be solved by taking a straightforward answer and then hurt the players for over complicating it.  Only use this technique in extreme cases. It can condition your players to do things in a new, unusual, and equally bad way.

Meta game Issues

Many of the problems with overthinking sections of D&D are actually issues with meta gaming. While it may not be overt meta gaming, you should still try to avoid this behavior in your players.

The best way to counter meta gaming is by asking your players to think about what their characters motivations are. Asking “What would your character do?” gets them thinking about how their character is not actually them. Then they may take different actions than the player would in the same situations. Be sure to gently remind your players to think about who their characters are often and you can be sure to see the overthinking problem diminish over time.

Putting it all Together

There are a number of ways to stop your players from overthinking every one of their actions. Increasing the complexity of trap instead of having a simple one will cut down on players thinking about worst-case scenarios. Subverting expectations will go a long way in managing the overly cautious player. Making sure your players don’t meta game and making tasks time-sensitive will kick-start player actions.

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