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Character Alice wants to pickpocket Character Bob. If Bob isn't actively anticipating this (e.g., sitting & drinking some ale), does Bob roll a perception check or does Bob use his passive perception score?

If Bob is actively anticipating the pickpocketing, does Bob get advantage on the perception roll when Alice attempts to pickpocket him?

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closed as too broad by daze413, Thomas Jacobs, KorvinStarmast, Sh4d0wsPlyr, enkryptor Apr 7 '17 at 14:52

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

  • \$\begingroup\$ The question Passive Perception confusion (LMoP-spoiler!) might be relevant. The question is about another kind of situation, but I think the answers are general enough to provide some help in this situation as well. \$\endgroup\$ – DrPhil Apr 7 '17 at 9:04
  • \$\begingroup\$ Hello and welcome to the site! If you haven't already, check out the tour, to see how different the stack is compared to other Q&A sites. On your question, the first might be a duplicate of the one DrPhil links above. The second should really belong in a separate post, don't worry about multiple questions, we actually encourage it to help focus answers more. \$\endgroup\$ – daze413 Apr 7 '17 at 9:05
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    \$\begingroup\$ Possible duplicate of Passive Perception confusion \$\endgroup\$ – Sh4d0wsPlyr Apr 7 '17 at 13:31
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Passive checks are for DM, not players

Passive checks in 5e aren't about characters "doing something passively". They are about players not making rolls (that's why they are "passive"), but DM still getting a check result:

A passive check is a special kind of abilily check that doesn't involve any die rolls. Such a check can represent the average result for a task done repeatedly, such as searching for secret doors over and over again, or can be used when the DM wants to secretly determine whether the characters succeed at something without rolling dice, such as noticing a hidden monster (Player's Handbook, page 175)

When Character A wants to pickpocket Character B, the player should make a roll, or DM can use a passive check instead. The decision is up to DM, it depends on if the DM doesn't want the player to suspect of something by rolling a die.

DM can also use passive checks when the result should be more predictable - for instance, Perception check for a guard on duty. In that case DM can make it for an NPC. But the main use case is making a passive check for a player's character without warning the player.

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As a DM, I would separate this into two separate actions. Alice needs to (1) get close enough to Bob to attempt to pickpocket him, and then (2) actually pick his pocket.

How Alice handles getting close to her target is situation-dependent, and there are several different options. She could find a reason to walk into Bob, or she could try and unobtrusively walk behind him, or she could sit next to him and start a conversation. You could resolve these with (for example) Deception, Stealth (versus passive perception), or Persuasion, with success indicating that Bob isn't suspicious of Alice's proximity. There are many other possibilities as well.

Once Alice is close enough to Bob, she can attempt to actually pickpocket him; this is a Sleight of Hand check at whatever DC you as the DM determines is appropriate. DC15 is a good default, and you might adjust it based on how successful Alice was at getting close to Bob. For example, if she sat next to Bob and started a conversation, but failed her Persuasion check, you might narrate that Bob was suspicious and scooted his chair away a bit, raising the DC to 20.

Since Sleight of Hand is already inherently stealthy, I would rule that any success results in undetected pickpocketing, and a failure doesn't result in Alice's pickpocketing being detected. (If Alice rolls a 1, I might narrate that they bungled the attempt so badly that it was obvious what they were doing).

If Bob is being vigilant — intentionally watching for danger — then I would let him make an active Perception check to notice a pickpocketing attempt.

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I don't think this exact situation is covered in the rules. There are many ways to make a fair ruling at the table. Here is a list of a few examples, but I am sure there are many more ways to rule this situation.

  • Use the same rules as for Hiding (PHb. 177), but use Sleight of Hand instead of Stealth. If Character A succeeds they pickpocket the item without detection and if A does not succeed they do not get the item and they are detected.
  • Character A uses Dexterity (Sleight of Hand) to contest the Wisdom (Perception) of Character B. If A wins, the pickpocket succeeds without detection. If B wins, the pickpocket attempt fails and A is detected. On a tie, the attempt fails, but A is not detected.
  • Character A makes a Dexterity (Sleight of Hand) check, the DC is determined by the DM based on the situation. On a fail, character A is noticed and on a success Character A pickpockets the item.
  • Character A makes a Dexterity (Sleight of Hand) check, the DC is determined by the DM based on the situation. On a fail, character A does not pickpocket the item and on a success character A pickpockets the item. Regardless of the outcome, Character A will also have to try to stealth using the hiding rules to avoid detection.

Personally, I prefer the last alternative as it has a chance of some interesting outcomes that are impossible in the other alternatives.

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A passive Perception check is appropriate, at disadvantage

As the PHB says under Passive Checks (p 175):

A passive check is a special kind of ability check that doesn’t involve any die rolls. Such a check can represent the average result for a task done repeatedly, such as searching for secret doors over and over again, or can be used when the DM wants to secretly determine whether the characters succeed at something without rolling dice, such as noticing a hidden monster.

I've highlighted the two reasons given for using a passive check, and expand on each below.

1. The average result for a task done repeatedly

Firstly, doing things repeatedly: passive Perception is normally applied to guards doing their job, which is constantly keeping watch, and to adventuring PCs who aren't distracting themselves with other tasks such as making maps. It represents a state of alertness in which a creature is on the look out for trouble.

Your character B drinking ale is not on the look out for trouble, but their senses haven't gone completely AWOL either: they should have a chance of spotting trouble, but not as much as if they'd been guarding a gate or crawling through a dangerous dungeon. For creatures like this, it's reasonable to allow passive Perception, but at disadvantage to represent the fact that they are not being alert.

If character B were making a map, or searching for treasure in foot locker, then they are distracted. The rules give the DM latitude to rule that such a character cannot benefit from passive Perception. But to be honest, character B is probably about as alert to danger as they would be nursing a pint in a tavern. So again, a passive Perception check with disadvantage is justified.

2. When the DM wants to secretly determine the outcome

A common reason for secretly determining the outcome of an ability check is to reflect ignorance or a lack of awareness. The passive check keeps both the PC and is player in the dark, and it avoids meta-gaming. That's appropriate here: character B is unaware of character A's intentions and so can't play an active part in the scene, unless and until they notice what's going on. And here noticing is a purely passive thing.

So a passive Perception check - with disadvantage - is warranted by the rules on passive checks.

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  • \$\begingroup\$ Just because I'm curious, how to you use a passive check with disadvantage? The point of Passive perception as stated in your quote is to do something without rolling, so how do you apply disadvantage to that? \$\endgroup\$ – John Grabanski Apr 7 '17 at 13:26
  • \$\begingroup\$ RAW, a passive check with advantage or disadvantage adds or subtracts 5 from the passive check number; e.g. if you have a passive perception of 14, and the DM rules that the situation calls for a disadvantage, you would only notice something that has a DC 0f 9 or less. \$\endgroup\$ – Phil Boncer Apr 7 '17 at 14:25

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