Scenario: An arcane trickster casts disguise self as a blind old man.

In a crowded room, his accomplice distracts the target, while the arcane trickster tries to steal his pouch of gold. As a DM, what would you have him roll?

I am trying to solve a minor disagreement between a player (me) and a DM. He felt like I should roll a stealth check followed by a sleight of hand check. I thought I should roll a sleight of hand check with advantage since I had gone to all the trouble to orchestrate the distraction with a party member and disguise myself.

It's up to the DM

This is a series of events orchestrated by the party that may require one or more ability checks. In this scenario, what happens is described on page 174 of the PHB:

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

In general, the player will describe their attempted action, and the DM will then call for any roll(s) and what they are.

If your DM felt like it should play it one way, then that's way it plays out.

There were lots of ways this could have played out, but ultimately it's the DM's call as how they're going to adjudicate it.

There could have been:

1. 2 rolls. One roll to for the distraction(Deception), one roll to steal (sleight of hand)


2. 1 roll. Sleight of Hand (includes the sneaking) with advantage for working together.


3. What your DM did may have been that in their mind, you did need to sneak up separately and this required a separate stealth roll. This is also reasonable if they felt the circumstances required it.


4. Any other option that the DM felt would tell a good story

The important factor, and one you do not mention in your question, is whether or not you were trying to hide or move sneakily at any point.

Page 177 of the PHB says:

Stealth. Make a Dexterity (Stealth) check when you attempt to conceal yourself from enemies, slink past guards, slip away without being noticed, or sneak up on someone without being seen or heard.

IOW, check stealth when you are trying to either hide or you are trying to move without being noticed.

If you were standing next to the target and the distraction was used to make people look away while you grabbed the pouch and then you just stood there looking nonchalant without trying to leave then I don't see how stealth could apply. You are standing in the open and not trying to sneak so there simply is no stealth involved. As a DM I would roll the checks to see if the mark and anybody close enough to notice the pickpocket were successfully distracted, then have you roll sleight of hand, giving advantage only if everybody was distracted.

But if you were standing away from the target and used the distraction to move close, grab the money, then move back away from the target all without being seen then there is clearly a need for a stealth check to cover your movement to and from the mark. Even if a person does not see you actually taking the money, anybody who sees an old man quickly move up behind somebody then quickly move away is likely to be suspicious.

I think the underlying issue here is a misunderstanding of some very basic rules of 5th edition D&D, namely, there's no such thing as a stealth check or a slight of hand check.

5e, unlike previous editions, has no skill checks. It has Ability Checks. If a skill proficiency applies to the task at hand and the creature doing the task has proficiency with that skill, then they add their proficiency modifier to the Ability Check. Even in that case, it's still an Ability Check, not a skill check. So, understanding that subtle but important difference, the resolution of the situation becomes much clearer.

The situation calls for an Ability Check. Which ability is the correct one for this Ability Check? Clearly Dexterity. The DM asks for a (single) Dexterity Check. But wait, what about my skills? The DM can pick one or more skill proficiencies that apply, and if you have proficiency in any one of the skills that apply, you add your proficiency modifier to the roll.