When stealing something, do you need to roll both Stealth and Sleight of Hand checks?

Question

Scenario: An Arcane Trickster casts disguise self to appear 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.

Answer 1

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 because 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.

Answer 2

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.

In other words, 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.

Answer 3

No, you don’t need to roll

Your DM could rule that, because of your creativity and roleplay, there doesn’t need to be an ability check. From the Dungeon Master’s Guide page 236:

One approach is to use dice as rarely as possible. Some DMs use them only during combat, and determine success or failure as they like in other situations. With this approach, the DM decides whether an action or a plan succeeds or fails based on how well the player: make their case, how thorough or creative they are, or other factors. For example, the players might describe how they search for a secret door, detailing how they tap on a wall or twist a torch sconce to find its trigger. That could be enough to convince the DM that they find the secret door without having to make an ability check to do so.

Theoretically, assuming your DM allowed for it, your character wouldn’t need to roll any dice because your roleplay is good enough and makes sense in the world.

However, it seems that your DM wants some kind of roll

Not all DM’s allow roleplay to replace ability checks in every situation. Either they might not like the concept if it, they may not be convinced enough to warrant it or they might not feel its appropriate for the current situation. Whatever the case, they want you to make a roll.

I find that reducing the number of dice rolls makes the game more fluid. Additionally, the more you are made to roll, the higher the chance of failure is because you would have to pass both checks, which is statistically less likely than you only passing one or passing neither of them. If you are having to pass multiple checks, you are being set up to fail. This isn’t always a bad thing, sometimes a DM wants something to be a challenge, warranting multiple checks to succeed.

The way I would rule it is that you don’t have to roll a stealth check, you aren’t trying to hide or be unseen - you’re wearing a disguise, you’re in plain sight. Now, people likely aren’t going to notice you (unless their passive perception is exceptionally high or your disguise is exceptionally poor) or pay attention to you as your disguise means you blend in, you don’t need to roll a stealth check. Additionally, because your target is distracted, they likely aren’t going to notice someone sneaking up behind them anyway, further reducing the need for a stealth check.

However, I would make you roll a “sleight of hand” check (likely using Dexterity but I could see Charisma or Intelligence being possible alternatives) to see if you can successful pickpocket the target. I would grant advantage if your friend was distracting them based on the Working Together rule (though for it to apply, your friend’s player would need to describe how they are distracting your target, not just say “I distract him”).

As a side note, there is also the idea of “passive stealth” which might apply. I don’t know too much about it so I can’t give many details. Essentially though, its the counterpart to passive perception, where you aren’t actively trying to be stealthy, you just naturally walk quietly and go unnoticed. Your DM might try using that for future checks to reduce the number of dice rolls, it also may mean you don’t know when you’ve failed a check until its too late, which could be interesting.

Answer 4

It depends how you steal the item

The description of Stealth states:

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.

The description of Sleight of Hand states:

Whenever you attempt an act of legerdemain or manual trickery, such as planting something on someone else or concealing an object on your person, make a Dexterity (Sleight of Hand) check. The DM might also call for a Dexterity (Sleight of Hand) check to determine whether you can lift a coin purse off another person or slip something out of another person's pocket.

If you are stealing a coinpurse off the table behind the target, then you are trying to conceal yourself and your actions. Anyone can pick up the purse, but you need to do it steathily. You would roll stealth.

If you are pickpocketing the coinpurse out of the target's pocket, then you need to roll sleight of hand.

Acting casual is not covered by either stealth nor sleight of hand. Your won't help you do either, but may help you make an opening.

Answer 5

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.