Writing & Running Investigations in Dungeons and Dragons

Aug 10

Writing & Running Investigations in Dungeons & Dragons

Guest Writer: Dara Yapp

Investigations are one of the great staples of TTRPGs. They are a great non-combat challenge to give your players. A giant puzzle for them to solve. But it is also tricky to do right. An investigation can quickly become too boring and straightforward, too complicated and seemingly unsolvable or, as most often happens, your players just completely take it off the rails.

Especially for newer writers and/or GMs, the idea of an investigation might seem daunting. Of course, each investigation scene is different, and the best way to get good at this sort of thing is to practice, but here are a few tips on how to get started:

First, make sure you have a clear overview of the information you want the PCs to find, or where you want them to end up (and what information would lead them there. Then break this into small pieces and spread them out over your location. Try to think of which NPC would logically know what, and what kind of physical information could be found.

If someone was abducted, for example, there may be witnesses (the shopkeeper across the street, a few kids who were playing outside). There could also be scuff marks on the ground, an item left behind, or drag marks leading into wagon tracks. You can start at your initial event and work your way back to how this would have affected the world. Try to work in multiple dimensions and engage multiple senses (sometimes thinking ‘Wait, would this leave a particular smell?’ gives you just the extra clue you need).

Second, while laying out your breadcrumbs, try to make sure it is not one straight line. There are two main reasons for this:

Railroads are usually boring (sorry, train-enthusiasts).
If there is only one track to follow, one mistake from the PCs will turn that track into a dead end. Of course, that might fit the vibe you are going for, but generally, it is a lot less fun for the players.

The spreading out of your clues will naturally lead to there being more tracks, but try to look if there are bits of information you could add into the mix here. I tend to write investigations out like a flowchart; making sure there are at least three tracks to follow at the start and multiple ways to get to each important point.

Maybe there are multiple people to talk to or multiple locations of interest. If there was a murder, the PCs could choose to start by investigating the corpse, visiting the murder location, or questioning the witnesses. Give your PCs options.

Third, I would advise making sure that you haven’t ended up with just a series of skill checks. In my experience investigations are the most fun if RP is a big part of it. It is a great exercise in creative thinking, after all. Generally, your players won’t need you to prepare a lot of flavor, they will run with what you give them and add more themselves. But here are two tips for a good basis:

Make your NPCs more than ‘press button, get info.’ An easy way to make an NPC feel more fleshed out without too much effort is to give it a character trait and a quirk. For example:

Grumpy + Loves to collect seashells
Friendly + Large glasses that are way too large
Socially nervous + Keeps overly meticulous records

It is very simple but quickly makes the characters feel more alive. It could be useful to prepare a list of these, even, as your PCs will likely seek out NPCs that you had not prepared for.

Be flexible. If (or more likely, when) the PCs have a strange idea you did not prepare for, allow it. Never try to push them back on the path you had decided on. Maybe they go to a different NPC, but this one could just as easily have the same information another NPC was going to give them. Perhaps your PCs actually have a really smart idea! Reward them for it! You could give them a little more information, or give them fewer hoops to jump through. Moving with the players is always the more fun option, in my experience.

My last bit of advice on writing/preparing an investigation is this: Include a pineapple.

To give that a bit more context, let me tell you about one of the most fun investigations I have ever played. We were in a strange town and our goal was to find a secret hideout of a certain alchemist. We asked around a bit, but couldn’t figure it out and got horribly stuck. It was rather frustrating actually. But there was one tidbit we had come across that kept us going. The henchmen traveling to and from this hideout would occasionally buy a pineapple, a rare fruit in that area. We became OBSESSED with the pineapple mystery and kept trying to figure out what was going on with the pineapples. Following this strange, random detail, we finally managed to find our way to the hideout. And into the trapdoor mimic guarding it (a mimic that just so happened to like pineapples).

Related Article: D&D: Enhance Lore and Exploration Pillars with Different Types of Puzzles

Our GM told us afterward that he had been confident that he had prepared several good tracks to follow, and had already given us a good deal of information while we were asking around. We really should have been able to get there on that information, he said. The pineapple was just a silly little detail he threw in when he was finishing up his prep work.

Years later we still laugh about the pineapple. And while it was the most frustrating investigation I ever played in the moment; in hindsight, it is my favorite. All because of the pineapple.

So, if you are absolutely, completely, 100% sure you have prepared enough information for your PCs to follow: Throw in a silly little detail. Every investigation is improved by pineapples.

That’s it! You are more than ready to write and run a great investigation! Remember though, inevitably, things will go wrong. There is no way you can predict all actions the PCs may take or the weird train of logic they might decide to go with.

When this happens, don’t beat yourself up about it. You are only human. Always see if you can just roll with it (see the ‘be flexible advice’ above). If that’s not an option (if the PCs point out a contradiction, or you forgot to tell them something), know that it is not a big deal. Just apologize, readjust, and move on.

Afterward always have a look if there is something that you could pre-empt next time, something you could learn from (perhaps there is a rule section you should look over again, or the players always tend to approach problems from one way and should be shaken up a bit). But remember not to beat yourself up for the good ol’ human error. Investigations are tricky, and if your PCs made their way through in one piece without ending up in utterly the wrong place, you already did a great job.

Go have fun!

Dara Yapp is an all-around geek and maker of pretty things; whether by sewing, painting miniatures, or creating worlds, stories, and adventures. You can support her and find links to her other works here: https://ko-fi.com/darawhyy

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