Can any spellcaster use Mage Hand to perform a Sleight of Hand check?

Question

The description of the Arcane Trickster rogue's Mage Hand Legerdemain feature (PHB, page 98) states:

Starting at 3rd level, when you cast mage hand, you can make the spectral hand invisible, and you can perform the following additional tasks with it:

• You can stow one object the hand is holding in a container worn or carried by another creature.
• You can retrieve an object in a container worn or carried by another creature.
• You can use thieves’ tools to pick locks and disarm traps at range.

You can perform one of these tasks without being noticed by a creature if you succeed on a Dexterity (Sleight of Hand) check contested by the creature’s Wisdom (Perception) check.

In addition, you can use the bonus action granted by your Cunning Action to control the hand.

Why don't the first two points hold for any spellcaster with mage hand? By looking at the mage hand spell description, it seems that any spellcaster can try to steal something from a pocket (a pocket is an open container, right?)? If so, should I call for a Sleight of Hand check with disadvantage (since the hand is visible) in this case?

Mage hand's description (PHB, page 256) states:

A spectral, floating hand appears at a point you choose within range. The hand lasts for the duration or until you dismiss it as an action. The hand vanishes if it is ever more than 30 feet away from you or if you cast this spell again.

You can use your action to control the hand. You can use the hand to manipulate an object, open an unlocked door or container, stow or retrieve an item from an open container, or pour the contents out of a vial. You can move the hand up to 30 feet each time you use it.

The hand can’t attack, activate magic items, or carry more than 10 pounds.

Answer 1

No, the first two points don't hold for any caster with Mage Hand.

Pickpocketing isn't just taking something from a pocket; it's a subtle skill which requires doing so unnoticed, after all. This is more than just "doing it while the victim's back is turned" - the human body registers slight touches and subtle sensations, like the weight of an object. A pickpocket knows how to beat these senses - by touching the victim in other places to confuse the senses, for example.

But the Mage Hand is implied to be clumsy, with limited dexterity - not conducive to stealth.

(Note that nothing in the Mage Hand description says that the hand has significant dexterity - it can "open an unlocked door", for example, or "pour the contents out of a vial", but apparently not manipulate lockpicks or disarm traps, which requires more precision. It's limited almost exactly to simple tasks that you don't have to practice.)

So it's not that the Mage Hand eliminates the normal skill check as such - instead, the rules as written do not contain a "normal" skill check for picking a pocket with a Mage Hand. (A standard thief can't pick locks with a Mage Hand either, even if they somehow have one.)

Most people can undo the buckle on a bag, or shoe. But can you do so so swiftly and subtly that the holder of the bag (or wearer of the shoe) doesn't even notice? Try it. It's not as easy as it sounds. It needs significantly more manual dexterity than just being able to undo a buckle - it's more like being able to play a piano.

Under the old-school skill system of 3e or 4e, the correct way to handle this would have been with a skill roll and an extremely hard DC - as GM, personally I'd have set the DC 10 or even 20 points higher than the usual for that kind of pickpocketing. The old skill system would then have allowed top-level characters to pull it off anyway.

But 5e discourages this "everything is technically possible with the right roll" approach, in favour of limiting skills to "actions anyone could attempt". "Pick a pocket with a magical force" isn't something anyone could attempt, and there's no obvious RAW reason why being able to pick pockets by the normal means would help you use a Mage Hand to do so.

(And it is typically next to impossible to pickpocket successfully with a fully visible, somewhat clumsy, disembodied hand. So even a disadvantage is not enough penalty - it should just be impossible.)

Legerdemain clearly gives the hand more dexterity, not just invisibility. This allows for more complex tasks.

Short answer

If the standard hand doesn't have enough manual dexterity to pick locks or disarm traps, it doesn't have enough for the equally tricky task of picking pockets.

Answer 2

Normally, Mage Hand can not be used to retrieve or stow items on another creature, without permission from the creature you are stowing or retrieving the item from. The spell only allows one to stow or retrieve items from an open container, and a creature is not an open container.

The arcane trickster ability is more precise, and says that one can stow or retrieve items being held by another creature.

Since this is a new ability that is not normally granted by mage hand, one must presume that mage hand normally can not stow or retrieve things being held by another creature, as another creature is not an open container.

Answer 3

You, a spellcaster with Mage Hand, can attempt to stow or retrieve. You, the player, don't call for checks: the GM does.

What check should the GM call for? Anything, or no check at all. I think your intuition is right: it should be harder for the non-Trickster than for the Trickster. But that doesn't mean a check is even necessary.

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By the way, this isn't intended as a frame challenge or as a criticism of any particular playstyle: just a nod to how we always say the game is played:

1.The DM describes the environment. ... 2.The players describe what they want to do. ... 3.The DM narrates the results of the adventurers' actions. (PHB p.6, "How to Play")