[RPG] Do Sleight of Hand checks cover stealthiness

dnd-5eskillsstealth

The PHB and basic rules describe Sleight of Hand checks as follows:

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.

Say Bob wants to steal Alice's wallet without her noticing. As a DM, should I call for only a Sleight of Hand check, or also for a Stealth check, to determine whether Bob manages to do it without being noticed?

While the description doesn't mention anything about being furtive while stealing these things, planting implies it is without the person's knowledge. But then again, Perception checks are (always?) pitted against Stealth checks to determine whether someone perceives something else.

Best Answer

It depends.

The most common way in reality is to do so in plain sight. Often there's a distraction, e.g. a light bump or such used as a misdirection for the theft. This kind of thing is part of the Sleight of Hand skill; that's what it's for.

If your player doesn't want their target to be able to think back to what happened and infer who likely robbed them, then you may ask for an additional Stealth check to determine whether they were seen.

But failing the Stealth check wouldn't fail the theft - though your player may, finding their target looking at them, decide against continuing.

Additionally, if it's a while since the robbery occurred, it might make more sense to have the target do a "memory" check (using a general Intelligence check) to see if they remember the circumstances, though as far as I'm aware there are no rules governing this.