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When you want to steal something you use Sleight of Hand to check whether you are detected or not.

Thus I assume Sleight of Hand to be contested by the targets/surroundings passive perception. I may be already wrong here, but the text about Sleight of Hand in the PHB does not say that it is a contested roll.

The problem occurs when one wants to steal a Horn around a guards neck or a potion from his belt when he is currently in a fight with you. Can I do so mid-combat? The player handbook does not offer a "steal" action or something similar.

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    \$\begingroup\$ Minor clarification: When a player states their character is attempting to steal something, the DM may ask them to make a Dexterity (Sleight of Hand) check. \$\endgroup\$ – Marq Apr 18 '17 at 19:34
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    \$\begingroup\$ There are actually two different questions. First one: a player announces "I try to steal a potion from his belt". How DM should represent that mechanically? Second one: Can the PC do that unnoticed? \$\endgroup\$ – enkryptor Apr 19 '17 at 9:16
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Yes.

Anyone can attempt to use Sleight of Hand to steal something mid-combat. For most PCs, this will require their action to make this attempt. Others may be able to use their bonus action.

As for whether or not the creature uses its passive Perception or a contested check would largely fall to the DM's discretion. Personally, I would look to the description in the rogue class for this sort of action since two of the roguish archetypes in the PHB specifically call out Sleight of Hand.

First, the Thief archetype on PHB p.97:

Fast Hands
Starting at 3rd level, you can use the bonus action granted by your Cunning Action to make a Dexterity (Sleight of Hand) check, user your thieves' tools to disarm a trap or open a lock, or take the Use an Object action.

and on PHB p.98 under the Arcane Trickster archetype (emphasis mine):

Mage Hand Legerdemain
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.

In the case of Fast Hands, it is not specified and the choice of passive/contested would therefore be left up to the DM. For Mage Hand Legerdemain, it specifically states that it would be a contested check.

As a DM, I would first consider whether the creature was aware of your presence. In a case where you have not been seen (you were hiding before combat began), I would probably use the passive perception. However, if the creature is aware you are out there somewhere (you hid after it initially saw you) then it makes sense to me to use a contested check because the creature would be actively looking for threats at that point. If you weren't hidden at all and attempted to steal an item while engaged with the creature, I would probably also apply disadvantage if you couldn't give me a reasonable explanation of how you might do it without them noticing (see examples below). And of course, there are some items that I may rule were impossible to steal at that point in time.

Example 1:
The PC moves as if to grab the jailer, but it is really a distraction so he can palm the key sticking out from the jailer's vest pocket.

Example 2:
A rogue attacks with his main hand. At the end of his attack action, while the creature is still distracted by the attack weapon, his off hand darts in during his bonus action to steal a potion.

Example 3:
The barbarian attempts to steal a dagger from their opponent's belt sheath without any distraction at all.

In examples 1 and 2, I would allow them to roll contested checks. Example 3 would be rolled at disadvantage.

One last note, I would apply these same principles to any Sleight of Hand attempt used outside combat as well.

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  • \$\begingroup\$ I'm not sure your example is "in combat". Distracting the target is often part of pickpocketing something. \$\endgroup\$ – Ling Apr 19 '17 at 7:46
  • \$\begingroup\$ @Ling There isn't anything saying that pickpocketing must be done outside combat. The example I gave could be used in either case. In fact, the wording in both the Rogue sections and in the new Unearthed Arcana feats for skills (which I believe is what prompted the original question) give you direction on where/when it could be used on your turn (bonus action). \$\endgroup\$ – Evermeet Apr 19 '17 at 11:53
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This is an improvised action, so it's up to the DM:

The blue box on page 193 of the PHB states:

When you describe an action not detailed elsewhere in the rules, the DM tells you whether that action is possible and what kind of roll you need to make, if any, to determine success or failure.

As you mention, there is no "steal" action (though the disarm attack may serve as a good substitute), thus it is up to the DM to determine how to resolve the action you describe. They may call for a skill check against a DC, a skill contest, or not even require a roll at all. And it is also up to the DM to decide if Sleight of Hand applies in your situation.

I hate to leave you with an answer as nebulous as "It's a DM call" but the implementation of many skills and actions is left up to the DM in 5e. So the correct answer in this case as to whether this is possible is: If the DM says so, then it is; and they will tell you what you need to do.

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    \$\begingroup\$ I generally agree with you, but the newest unearthed arcana adds a feat that allows you to "use slight of hand as a bonus action"... What would I use that for, then? (I might make this into a separate question, as the rules seem to be silent on that matter) \$\endgroup\$ – Patta Apr 18 '17 at 18:47
  • \$\begingroup\$ @Patta I don't mean to sound sarcastic or belittling, but you would use it for whatever the DM told you that you could use it for. Or you could ask "could I use my bonus action sleight of hand to...?" The rules tell us the kinds of things that skills encompass, but not always how to use those skills in the game. The DM has to fill in the gaps. \$\endgroup\$ – Adam Apr 18 '17 at 18:51
  • \$\begingroup\$ Yea, I know. I just don't like the implication. But there is no need to discuss the design of 5e here, that would be too much. \$\endgroup\$ – Patta Apr 18 '17 at 18:53
  • \$\begingroup\$ @Patta The Unearthed Aracna are at play test/draft level, not on par with the more "polished" rules already published. \$\endgroup\$ – KorvinStarmast Apr 18 '17 at 21:49
  • \$\begingroup\$ Yes, but "you can use sleight of hands as a bonus action instead of an action" implies that there is something you can do... \$\endgroup\$ – Patta Apr 18 '17 at 21:59
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The DMG rules on disarming make more sense in combat:

A creature can use a weapon attack to knock a weapon or another item from a target's grasp. The attacker makes an attack roll contested by the target's Strength (Athletics) check or Dexterity (Acrobatics) check. If the attacker wins the contest, the attack causes no damage or other ill effect, but the defender drops the item.

Sleight of Hand, as contested by passive perception, is more of a stealthy thing; if you're in combat with an enemy, they have probably already noticed you.

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    \$\begingroup\$ What if the player wanted to steal it without the enemy noticing he had stolen it? \$\endgroup\$ – Marshall Tigerus Apr 18 '17 at 18:50

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