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For context, this is my first adventure as a DM.

About 40 minutes into the first session, while investigating the rumours about a ghost ship, the group meets with Aleyd Burrows, a skilled veteran, Captain of the Guard and a very important figure.

She gives them various pieces of information and sends them on their way with new leads. As the party starts to leave, the last player walks up to Aleyd, shakes her hand and tries to steal her purse. Luckily he passes the Sleight of Hand check with ease since he rolled a 16+8 (he's a rogue with Expertise). (I chose a DC of 20 without disadvantage: Aleyd is usually quite alert, but the player did make a very natural “Thank you”+handshake, and Aleyd didn't have a reason to be more alert then usual.)

However, I do not know how to deal with this had he failed.

Knowing him, he is likely going to pull similar stunts.

P.S. I did talk with him afterwards, and he promised to be more mindful from now on.

He enjoys fooling around, but he is trying to do so without reducing the fun of the others.

He also set off a bit of a conflict with another thing he did, which me and the other players commented on. He did thoroughly apologise for it, and they spent some more time talking it out.

I mostly want to know how to deal with deal with such situations without stepping out of the “in game” position.

This is not uncommon since many players come from video games, wantonly stealing from and murdering NPCs. NPCs in roleplay games tend to be smarter though, and have logic.

Give them a reputational cost.

They didn't interact with anyone else. If they check their wallet after, they'll know that it was probably that thief who stole from them. So what do they do? Not fight a bunch of murderhobos. They go to the pub and complain about these so called 'adventurers' who rob and steal from everyone they meet, and then in that village or town, people refuse to serve that thief and anyone associated with them for fear of having their stuff stolen. Don't make it universal, unless they repeatedly do stuff, but if they harass NPCs, NPCs won't want to talk to them unless very seedy, and quest givers won't give them useful info.

If they had failed the check, the NPC would slap their hand away, swear at them, and march off to tell people how untrustworthy the adventurers were, unless she really really needed them.

Explain morality. Make sure they know being a thief doesn't mean they are supposed to steal from everyone they meet. Allies are supposed to be safe- just as being a fighter doesn't mean you stick your sword in random allies, being a wizard doesn't mean you turn the local cleric who heals you into a frog, being a thief doesn't mean random stealing.

Give them a common sense check. Sometimes it would make sense to steal from an ally. A sufficiently mercenary group might want to steal from an ally if there is a valuable enough possession, and that's a quest and a heist. If their ally has a rare and powerful magical item, maybe they can get it off them, and maybe it's worth the reputational cost. A few gold probably isn't worth that risk.

Don't let the player derail things

Many players who are new to tabletop RPGs enjoy the feeling of liberty that stems from not being subject to a rigid mechanical engine, like in a computer game or a board game. This makes trying unconventional things like petty theft very appealing to some.

However, pulling off stunts like this detracts from an even bigger concern: a tabletop RPG is supposed to be something that you do together, as a group activity. Wanton theft and other troublemaking can quickly change the game from "a group of heroes adventuring together" to "Tuikku the Rogue stirs trouble and everyone has to fix it, every time". That's where approaches relying on in-game consequences fail --- even if you punish just the thief in question, and even if the punishment is fair, it still winds up drawing lots of time and energy from the entire group.

Therefore, as you've already opened conversation with the player in question, the next time they want to do something that'd potentially cause trouble for the entire party, say something like this:

Doing that would likely result in the rest of the session being spent to undo whatever damage or complications might happen. Given the magnitude of the decision you're making, I'm sorry but I'm not letting you do it unless everyone is on board.

(remember that everyone includes yourself. It's not something you should do lightly, but if you're uncomfortable accommodating for any player action, you have every right to veto them)

This has worked well for me beforehand --- the strong point is that it forces the player to consider the consequences of their actions on the whole game. Are cheap laughs or exercising their theft skills just for some coins really worth of half an hour of everyone's table time to resolve the incident and its aftermath? It's also flexible, as the same argument applies equally to murdering non-threatening NPCs and similar "rash" decisions.

Alternatives for sticky-fingered PCs

That said, if your player wants to maintain theft as a part of their character, you have options that don't require stealing the focus or risking the party at the table. One option is encouraging thievery as a Downtime activity, making the character earn some additional coin between adventures. You can ask the player to cover their crime sprees in a few sentences:

GM: "Ok, it's been four days since your last adventure. Do I remember correctly that Tuikku the Rogue was doing theft as a downtime activity? Roll how much money you made, and then briefly describe what you stole during that time, and from who."

Tuikku's player: "I mostly just picked purses in the marketplace from stuck-up burghers, and also swiped and fenced an ornate ring from a handsome gentleman."

If you feel the downtime action needs a little something extra, you can also drop in plot hooks:

GM: "This morning, you caught word that the gentleman has hired a large group of investigators to look for that ring --- for far more coin that the trinket is worth. They're roughing up people for information, and your fence has gone off the radar for their own safety. What's with that thing?"

You can also ask your player to come up with plot hooks or details of stolen items if you like.

this way, your player gets to engage in rampant theft and have that as a part of their character without it detracting from everyone else's sessions.

In a real situation, no one would ever try that sort of thing. Would you talk with someone who can probably kill you in a second and then try to steal her purse? No way.

This kind of issue can be caused by 2 things:

• The player is testing your limits to check if you are going to punish that kind of behavior.


• Maybe the player was not really aware that Aleyd can kill him easily or just throw him into jail until the end of his life.

There's multiple kinds of possible punishments. Throwing the character into jail for years is the logical solution, but the player will likely just make a new character.

Instead of this, you can:

• make Aleyd confiscate all of the character's belongings as a fine.


• start a fight between Aleyd and the player. Of course, the player's character can't win this fight, but Aleyd does not want to kill him; she just wants to impose a fine and give him a good scar on his face.


• make Aleyd neutralize the player's character, then say to the rest of the group: "You better look after him; one day you're all gonna die and it will be all his fault."

Actions have consequences

the last player walks up to Aleyd, shakes her hand and tries to steal
her purse. Luckily he passes the Sleight of Hand check with ease since
he rolled a 16+8 (he's a rogue with Expertise).

The games basic premise is this (Basic Rules, p. 4):

1. DM describes the environment/situation


2. Player describes what they want to do.


3. The DM narrates the results of the adventurers’ actions. (Only roll the dice when the situation is in doubt).

Per your comment, you assigned a DC of 20 for the attempt. In the basic rules (p. 61) we find:

Task Difficulty DC

Hard 20

Very hard 25

Nearly impossible 30

If you set a DC of 20, and they rolled a 24 - fine! The rogue pulled it off. (See below). If you had set a DC of 25, and the rogue failed (24 being the roll+mods) an angry Captain of the Guard is still shaking the hand of the thief and notices the attempt to steal her purse! Trouble just happened and needs to be resolved. Someone just made an ally into a enemy, or, maybe some fast talking can get them out of this - "Captain, I was just showing you how good we are a this undercover stuff ..." Will she buy it?

DMing note: you can always assign disadvantage to a roll for an ability check if the circumstances around it call for that. Is there a reason that you did not assign disadvantage to this blatant attempt at theft in the presence of the mark? You don't have to, but it seems a valid use of that mechanic. From your comment, you chose not to assign disadvantage. That is certainly your call to make.

The DM can also decide that circumstances influence a roll in one direction or the other and grant advantage or impose disadvantage as a result. (p. 60, basic rulse)

If the player didn't set up the situation such that the Captain of the Guard was distracted, the sleight-of-hand check will be a lot harder than if she was distracted. There is no need to be shy about using advantage and disadvantage as a DM. It's there for you to use.

But hey, the rogue succeeded! Nice pocket picking there! This act did not occur in a vacuum.

The captain notices her missing purse

The game world reacts to the characters' decisions and actions.

Either the Captain knows who she last had a conference with, and suspects that her purse is where they are, or, the Captain (your roll) does or doesn't remember who she was last in a meeting with when she knew where her purse was.

If you set it up as the latter case, or if you don't want to just decide, make an unmodified Intelligence Ability Check, or an Intelligence (Investigation) check on behalf of the captain. (I'd do it behind the screen ... DC 10 or so is suitable here).

1. If she misses the roll (your rogue need not know the outcome) she doesn't remember them in association with the purse and thinks she misplaced it.




2. If she makes the roll, well then, trouble for the rogue.

If the party gets a visit from the captain ...

... a squad of guards (NPC, Town Guard) armed with heavy crossbows, with the Captain leading them, tracks down the party (or just the rogue) and at crossbow point suggests that the rogue return the purse.

Further consequences are then figured out based on how the party responds.

Lesson Learned for future things like this

The world reacts to what the players do. The above example is but one way to account for that.

These are all good answers, but there's one thing you should do in addition to all of the answers provided.

Let the Player Know the Consequences Before They Roll

In real life, we know that our actions can have severe consequence against us in the future. And a real thief knows that stealing from someone of extreme importance to them for a few gold is not a risk worth taking.

But, these kinds of details can get lost in abstraction if the player is simply thinking of the mechanical aspects - they might think "I can get a few gold for doing this" and not accurately consider the consequences.

So before a player tries to make such a roll that would have dire consequences, you should say something like:

Are you sure? If you do (x), then (y) will happen, and it will have (z) consequences on you in the future.

In this case, (x) would be stealing from the Captain of the Guard, (y) would be them finding out they were robbed by a thief and/or immediately knowing that they are being robbed, and (z) being losing a ton of reputation with the town, and potentially being thrown in jail and forced to pay a hefty bail.

This is not just a good idea for crimes, but for any attempt at a skill check by a player that is likely to lead to some dire consequences if they fail (or especially if they succeed!).