Hey, what's up? I'm currently planing for my first ever GM session next week. Since i want to keep it simple, we agreed on a one building setting. The basic idea is that the players have been hired as hired help for a town festival and one idea for one activity I had is the good old pick pocket. sometime during the party one of the guests will notice that something has gone missing and it's up to the players to find out who did it.

Only problem is... i'm not quiet sure how to handle this kind of scenario the best. What kind of clues should i leave for the group if any? What's your experience how to handle these type of situation the best? I know this is a rather vague topic, but maybe one or two have played a similar scenario beforehand and has an idea that could help me with my planning.

Regardless, thank you all in advance for reading and i wish you all a nice day^^

Id play it like a game of Clue/do. Skill checks similar to 3rd or 4th edition would play well with this. Drop hints if needed.

Well... as with any gaming session... there's the way you'd think it should go, and then there's the way the players are gonna make it go.

Let's start with the easy part: The way it SHOULD be.

If the characters are the ones being tasked with solving the mystery, there must be a valid reason WHY they specifically were chosen. Do they have a connection to the innkeeper? Are they familiar and trusted Folk Heroes of the area? You'll need to have at least some plausible reason for why they have been entrusted with this responsibility and this authority. Then, you'll want a plethora of interesting, eccentric, shady, creepy and downright dangerous suspects in the crowd. "Look at this motley crew! It could be anybody!" 

Next... Law & Order the crap out of that place! ♫DUNDUN!♫ The actual thief needs three things: Means, Motive, and Opportunity. Make sure you flesh out the actual thief as fully and as deeply as any BBEG. But remember two things: 1. Try to make the bad guy sympathetic. You want your players to want it NOT to be that guy. That'll make it all the more satisfying when you reveal the truth and twist that dagger in their hearts. 2. Every bad guy sees himself as the hero of his own story. Make sure to play the bad guy as a hero. After all, notions like "right" and "wrong" are just matters of perspective. Go on YouTube and check out a video called, "The Case for Gul Dukat". It is absolutely ESSENTIAL reference material for making a good bad guy.

So, once you've got the setting mapped out, and the bad guy mingled in with the usual suspects, and the poop hits the proverbial fan... what happens? First, the players will need a way to secure the crime scene. Why doesn't everyone just make a run for it? Are the players responsible for investigation AND security? Or are there some local constabulary bruisers there as well, for backup? Once the scene is set... well... there'll be lots of questioning, which will involve Persuasion checks to convince someone to help you. There'll be Intimidation checks to coerce information out of a reluctant witness. There'll be Deception checks from the suspects to hide their lies. There'll be lots of Insight checks to try to determine who's lying. There'll be Perception checks to see if players notice fine details of a person that don't match their story. ("You said you were plowing your fields all day, but your boots are still clean!") There'll be Investigation checks as the players search suspects. There'll be Sleight of Hand checks as suspects hide things from the players. 

Yeah. There'll be a lot of skill checks. This is where the gameplay might get bogged down. Don't let repeated skill checks go on for more than a few consecutive rounds before something startling happens. Maybe somebody makes a run for it. Maybe all the candles and torches go out. Maybe somebody just flat out dies for no apparent reason. Maybe there's a knock at the door and a stranger walks in and he's just the creepiest and most suspicious looking person ever! But it turns out he's just a traveling merchant stopping in for dinner and a room. 

Hopefully after a few rounds of skill checks the players will be able to rule out a person, and let them go. Then they move on to the next one, and so on. Until finally there's only maybe two or at most three finalists. This is where surprises need to happen. Simply winning through cross examination will not be fun. Once they're sure they've got the right guy BOOM his henchmen bust in to rescue him! Now it's a running battle through the streets at night! Now THAT'S fun! All this time the party's barbarian with a combined Int + Wis of 15 has been bored stiff but now he gets to shine! It's just not D&D until somebody rolls initiative! So maybe the bad guy is heading for the docks to make a getaway on his ship. Can the party catch him before he escapes? Ideally the party found the item on him, he escaped, they chased him, he's getting away on his ship and then the wizard casts fireball at the ship then turns around and totally Horatio Caine's the crap out of it with the sunglasses and The Who blasting "Won't Get Fooled Again" as the ship burns down into the waves! 

That's how it SHOULD go.

Now let's look at what's gonna happen: The players will get drunk on their newfound deputized power. They'll rough people up for information. They'll threaten people's families. The rogue will be sneaking behind the bar to steal drinks while everyone else is working. The bard will suggest strip searches, starting with himself! They'll make the Stanford Prison Experiment look like pledge week at Omega Mu. So you'll have to set some firm boundaries. Maybe the local guards are good hardworking peacekeepers. They'll secure the scene AND keep an eye on the players while the investigation is going on. 

Just keep throwing stuff at the players. Keep them busy. If they get bored they'll cause trouble. Maybe there's a time limit. Maybe it was someone's medicine that was stolen, and that person will get sick or maybe even die without a dose. The more you keep the suspense and the action moving along, the less likely the players will be to get bored and start Abu Ghraibing the inn. 

If you've got two hours to kill, watch the movie "Clue" (1985). Tim Curry, Christopher Lloyd, Madeline Khan. It's a classic! And watch "The Case for Gul Dukat" on youtube. But most importantly...

HAVE FUN!