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I rolled a 20 on a stealth check and my DM thinks I have to reroll stealth everytime I perform an action. (I.e.: opening a door, walking up stairs, grabbing something.) If this were true I would have to reroll stealth a lot. I know that the drow that I'm sneaking by are supposed to make perception checks, but do I have to keep making stealth checks?

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Your DM is wrong

PHB p.177:

Until you are discovered or you stop hiding, that check’s total is contested by the Wisdom (Perception) check of any creature that actively searches for signs of your presence.

Hiding (as a verb) means "To keep oneself out of sight or notice" - it is not inherent in this definition that you cannot move or take any other action. Indeed the skill is called Stealth which means "The act of moving, proceeding, or acting in a covert way". It is entirely reasonable to "hide" in plain sight if the intent is not to be noticed rather than not be seen.

The only ways that a character ceases to be hidden is if somebody finds them (and communicates this to others who have not found them) by beating the Dexterity (Stealth) check with a Wisdom (Perception) check or if the character "stop[s] hiding" - a conscious choice. A new Dexterity (Stealth) check is only called for when you want to hide again after being discovered or circumstances change such that your method of hiding is no longer appropriate (e.g. you were hiding in a crowd which disperses, you move from a paved area to an area covered with fallen branches and leaves).

Remember, this cuts both ways: a really bad roll has to be kept even though eventually the player knows character will encounter someone with enough Wisdom (Perception) to overcome it. This is potentially a problem with out-of-game knowledge affecting game play but mature gamers can usually keep these separate OR the DM can roll Dexterity (Stealth) checks and keep the results secret from the players (equivalently, the DM can roll active Wisdom (Perception) checks and use the PC's passive Dexterity (Stealth) - the odds are identical). It also means that creatures sneaking up on the players only get one roll too which may be to the benefit or detriment of the players.

Doing otherwise will simply result in the character failing eventually. For example a character with +5 to Dexterity (Stealth) facing an opponent with a 10 passive Wisdom (Perception) will succeed 75% with one roll, 56% will 2 rolls, 42% with 3 and only 32% with 4. This is an unfair nerfing of a skill the player chose over another skill - does the DM require multiple Intelligence (Investigation) checks to find a secret door, multiple Dexterity (Athletics) checks to jump a chasm, or multiple Wisdom (Perception) checks to find someone who is hidden? The Alexandrian has an excellent article on this.

See these related questions:

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    \$\begingroup\$ This is a great point that isn't taken into account in the other answers, however, the Hide action is not the only use of Dexterity (stealth) checks. It's entirely possible to succeed at Hiding, then need to make another check to open a door silently. Failure on that check should not reveal your presence/location, but could put guards on alert. The important thing is to match the failure to the small check, not have one failure completely negate all the previous successes. \$\endgroup\$ – Derek Stucki Nov 21 '16 at 23:44
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The number of checks is a DM's call.

This ultimately comes down to play style and your DM's ruling. Some DM's like to break up a task into smaller chunks to heighten tension and the chance for failure. Others like to handle the entire series of actions with one roll.

Too many checks can make the skill worthless however, as you only have to fail once to fail completely. In general, a stealth roll should cover an entire complete action: Sneaking past a guard should not require a separate roll for opening the door, walking across the room behind his back, and leaving through another door. If a stealth task is very complicated or difficult, this should be handled with a minor penalty (or possibly disadvantage, though disadvantage can be a major hit to your chance to success depending on what your skill and the opposing ability check are.)

Discuss with your DM, since it is ultimately their call.

As for rolling a natural 20, sorry. That doesn't get you anything special under the standard rules. Only attack rolls benefit from a critical result (or an automatic failure in the case of a natural 1, for that matter). 20 is just a really good roll.

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As keithcurtis mentioned, this is up to the DM. Here is how I have handled it in the past (note: my group does use the critical success/failures on skill checks houserule).

When I ask for stealth checks, it will either be general or for a purpose. In the case of a general stealth check, it's just to beat passive perception of nearby enemies. For those purposes, your 20 would do you well until the point where you had to do something noisy (open a door) or something tricky (step passed the enemies in question when you could be seen).

If you were trying something with a specific purpose (e.g. try to quietly open the door and slip in the room) then it would last only for that action, and any future stealth would require further rolls (though, that roll would be "in place" if you moved into the room and stood still, as that was part of what you wanted to do).

This goes back to your intent on the roll. This is important because players, upon getting a great roll, will try to stretch it out as far as they can (I kid you not I once had a player insist that his high, non-critical roll on a lockpicking check should give him advantage on all locks in the building as they would be similar), while trying to limit what bad rolls mean (Oh, I only meant to sneak for about 10ft before stopping for the rest of the party because I rolled a 2). If you make them declare their scope, then their success and failure is entirely on them.

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Your DM should keep Stealth checks to an absolute minimum

As @DaleM points out, RAW says you make only one check. And I think it's a safe bet that the design intent was to do away with the increasing risk of failure that attends each successive check.

When extra Stealth checks are warranted

Your DM is within her rights to call for more than one check, but this must be a decidedly rare event. Possible reasons for making a second check are:

  • To add to the tension of the game.
  • When you are making yourself more noticeable by interacting with the environment, such as opening doors, stealing treasure or palming a trinket from under someone's nose.
  • When you try to get much closer to a creature without being spotted by it.

When they are not warranted

From this and other internet forums, I gather that many DMs will ask for a new Stealth check for mundane reasons, when it would be just as easy, and probably fairer to the hiding PC, to apply advantage or disadvantage to either the PC's Stealth check or the Perception check that it is contesting.

So, bad reasons for asking for a new Stealth check are:

  • There's a new creature that might spot you (no, the attempt at hiding hasn't changed, it's the creature that's different; the DM should use its Perception check).
  • New round: new check (if the circumstances haven't changed markedly, there's no need to call for a new check). In a similar vein: you've travelled 100 feet so it's time for a new check; you're in a new room/ corridor so it's time for a new check.
  • You are now lightly obscured instead of heavily obscured (no, obscurement affects Perception, not Stealth).
  • You have remained motionless for a minute (the shouldn't dismiss the existing check, but give it advantage instead, ie roll another d20 and use whichever result is higher).
  • The guard saw you go into hiding (no, the DM should give his Perception check advantage).
  • You are in dim light and have ducked behind a tree, giving you cover from bandit A but not from bandit B (the DM should decide whether to treat bandit B's Perception check differently from bandit A's, but should not require a new Stealth check).

Don't forget the Perception side of the coin

In particular, it's worth remembering that obscurement and concealment are attributes of the perceiver's point of view, so they should affect the perceiver's Perception check rather than the PC's Stealth check. For example, if I'm a human peering into an area of dim light, a creature hiding there 50 feet away will be lightly obscured to me. If I'm a half-orc with darkvision, it won't be obscured and it will be easier for me to spot.

The granularity of contested checks with advantage and disadvantage

With advantage and disadvantage, there are nine different permutations of contested checks between Perception and Stealth. For example, one permutation is a thief with Supreme Sneak moving slowly through light obscurement while a human guard stands watch: the Stealth check has advantage, the Perception check has disadvantage.

| Stealth check     | with disadvantage | [standard]    | with advantage |
|------------------------------------------------------------------------|
| Perception check  |                   |               |                |
|                   |                   |               |                |
| with disadvantage | permutation 1     | permutation 2 | permutation 3  |
| [standard]        | permutation 4     | permutation 5 | permutation 6  |
| with advantage    | permutation 7     | permutation 8 | permutation 9  |

That translates to nine likely levels of success: a wide enough range to account for the varied circumstances that a sneaky PC can find themselves in without adding the randomness (and ultimately the inevitability of a bad result) that comes from making multiple Stealth checks.

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There are a lot of great answers in here. I do not think that they touched on one element enough though.

Be absolutely sure that you are not rolling the dice, seeing the number and then that high roll is making you a bit more bold.

You need to:

  • Decide on your action
  • Roll
  • Accept whatever happens

DM Shouldn't do this:

  • Roll stealth to peep in room
  • Roll stealth to open door
  • Roll stealth to walk to chest
  • Roll stealth to open chest
  • Roll stealth to walk back to door
  • Roll stealth to close door

Every time you roll here, you're taking a risk of failure and it adds up. This amount of rolling is annoying and also makes it very risky.

Conversely, the player shouldn't do this:

  • Say they want to peep into the room
  • Roll stealth, get a 20
  • Say they want to open the door, go to chest, loot it and come back on that one roll.
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