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The party goes to sleep around the campfire, and one member volunteers to take the first watch. A couple of hours later, a dozen bullywugs try to stealthily ambush them.

The DM makes stealth rolls for each of the attackers and compares them to the passive perception of the character keeping watch. Inevitably, one of the bullywug rolls fails, and thus the ambush is detected. (Group stealth is nearly impossible, it seems.)

So the watch character is not surprised, and initiative ensues. But the character rolls a low initiative.

What happens next?

Do the bullywugs get to attack the sleeping characters before the watch can wake them? (At advantage, automatic crits, due to unconscious condition.)

That's how I played it as DM, but it seemed a little harsh. Am I parsing the rules correctly?

Random encounter during a long rest, with a watch, is a very common situation. What is the correct way to resolve it?

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  • \$\begingroup\$ Note that sleeping characters having the unconscious condition comes from XGtE and is thus, strictly speaking, an optional rule. \$\endgroup\$ – Kirt Jun 5 at 18:02
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    \$\begingroup\$ Sleeping characters having the unconscious condition also comes from the plain-English reading of "sleeping," which is the default for 5e. \$\endgroup\$ – nitsua60 Jun 6 at 2:03
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    \$\begingroup\$ @nitsua60 That is a ruling, though, not a rule. For myself, a plain English reading of "can’t move or speak, and is unaware of its surroundings" does not describe the majority of people that I have observed sleeping. In particular, the scream emitted by someone run through with a bullywug spear would be sufficient to wake most people up, in my experience. \$\endgroup\$ – Kirt Jun 6 at 2:16
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    \$\begingroup\$ "Group stealth is nearly impossible, it seems." Technically, they should have rolled a group check - if half or more of the bullywugs succeeded, the whole group would have succeeded. \$\endgroup\$ – nick012000 Jun 6 at 9:12
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    \$\begingroup\$ @nick012000 That is at the DMs discretion, PHB 175 states "the DM might ask for a group ability check" and furthermore "[group ability checks] most useful when all the characters succeed or fail as a group". This doesn't have to be the case for stealth, where it is very well possible for one character to fail and be spotted, while the others are still hidden. I think I will open a question for this to avoid discussion in comments. \$\endgroup\$ – findusl Jun 6 at 19:09
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The DM controls the narrative, not the mechanics

Random encounter during a long rest, with a watch, is a very common situation. What is the correct way to resolve it?

The "correct" way depends on the table expectations and the genre you are playing, not the game mechanics. To an extent, the DM can make sleeping in the wilderness as dangerous as she wants to. D&D 5e puts aside the mechanical approach to stealth, leaving it up to the DM almost completely. You can find some 'Sage Advice' on stealth in this podcast.

As a DM, think about decisions that the players could make and the consequences they should get as a result:

  • Is (not) being on watch a no-brainer? What are cons and pros?
  • Can players make meaningful decisions? Do they have or lack agency?
  • Do they have fun?

The next paragraph is analysing the ambush from the players' perspective.

What was the point of the watch if it didn't prevent an ambush?

The very point of staying on watch is to be able to wake up the party before the danger bursts in. If the only advantage of the watch is the chance of the watcher (not) being Surprised, the watch itself becomes meaningless.

It's a good idea to give a chance of spotting the enemy beforehand. However, rolling for every bullywug and comparing with the passive score is the antipattern known as "rolling to failure". The rules suggest using a Group check instead.

To make a group ability check, everyone in the group makes the ability check. If at least half the group succeeds, the whole group succeeds. (PHB, Ch 7, Working Together)

It still requires a lot of checks for NPCs, which isn't considered a good practice. The game is a story about player characters, not about NPCs.

There is a better alternative.

Ask for a Wisdom (Perception) check from the player and compare it with the passive Dexterity (Stealth) score of the bullywugs. If he succeeds, let him spot the enemy far enough to be prepared. If he fails, the danger bursts in - all the teammates are asleep and unconscious. The watcher being (not) Surprised makes little difference in this case.

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    \$\begingroup\$ If the only advantage of the watch is the chance of the watcher (not) being Surprised, the watch itself becomes meaningless Well said! That's the core of the issue. Also, your point about group checks and The game is a story about player characters, not about NPCs is a great way to frame who should make a check against what. Also like your use of a passive Stealth score. This will get a bounty when it is available. 😎 This is a scenario (ambush at night camp) that is common and commonly mishandled. \$\endgroup\$ – KorvinStarmast Jun 5 at 13:17
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    \$\begingroup\$ I would greatly appreciate if you could support or further explain this line: "It still requires a lot of checks for NPCs, which isn't considered a good practice." I am not sure what it is trying to say, and calling something a bad practice may be a bit much \$\endgroup\$ – Medix2 Jun 5 at 15:01
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    \$\begingroup\$ @Medix2 as in, the group check method it still requires rolling Stealth for every member of the NPC group. \$\endgroup\$ – Geoffrey Brent Jun 6 at 0:31
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    \$\begingroup\$ @Medix2 I called "a bad practice" making a lot of checks for NPCs behind the screen, providing the game is about PCs, not NPCs. Otherwise it turns out the DM is just playing with himself, so to say. This wastes players' time and is just boring. \$\endgroup\$ – enkryptor Jun 6 at 11:09
  • \$\begingroup\$ +1, but a word of warning: "The DM controls the narrative, not the mechanics" can be taken too far, into the "railroading" realm. I might say "guides"; if the players decide to kill the recurring villain the first time they pop up and the mechanics of combat say they die, the villain's dead. \$\endgroup\$ – minnmass Jun 7 at 4:09
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I can think of two things to do differently to make being on watch more useful and fun:

OK, the bullywugs were trying to ambush, but what were they doing before that? They could have been walking along croaking bullywug songs and then seen the fire. The PC could have heard them first. Sure, it's just as likely they were silently paddling up the burbling river, hidden by shrubs. But if there's a possibility, give the watch-person a chance to at least hear them from a longer way off and a few rounds to get ready if they do. 12 of anything is going to make some noise.

The other thing is that the frogmen don't know the player heard them. Combat shouldn't have started yet. The bullywugs are sneaking around the camp, probably signalling "you take the one on the left". They may not even have seen the watch-person. They'll just keep on sneaking into place, making sure they didn't miss anything or anyone, which might take a few rounds. Combat would start just after the sentry yells. Or the sentry might try to subtly kick the mage "psst...wake up" without the ambushers noticing (this is more common in "you hear a lot of croaking and splashing coming up the river" situations). That could go on for a while until combat needs to start. I've even seen players get ready to ambush the ambushers, solo, while the sleeping players can't believe what they're hearing.

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    \$\begingroup\$ (For reference, "wog" has historically been used as a short form of "Golliwog", which was an embarrassingly racist caricature of black Africans. Obviously that's not what you were intending here, but I might avoid that contraction in general. Just to avoid any possible misunderstanding) \$\endgroup\$ – Brondahl Jun 7 at 12:50
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    \$\begingroup\$ @Brondahl Huh...it turns out I am one. Seems as if it's mostly Greek/Italian. There's a local sandwich named a Dago and I cannot find a single person who knows that's a racial slur. Bulywogs are frogs who like swamps -- in America your really potent black slurs involve jungles and apes. So D&D is probably safe with bullywogs. But I guess it's tough to abbreviate. \$\endgroup\$ – Owen Reynolds Jun 7 at 13:38
  • \$\begingroup\$ But they are called "bullywugs" not "bullywogs", so you could abbreviate them as "wugs" :-P \$\endgroup\$ – RHS Jun 7 at 14:24
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One of the things that needs to be determined is how far away were they when they were detected? If they were detected far enough away (and this does seem to be the point of having a guard), then the enemy would have to spend their turn moving into range to attack the party. This question of "how close were they" is usually the critical one to determine whether a silent attack succeeds or not. Since there would be no point to detecting silent intruders if you couldn't detect them soon enough, I would generally rule that the ambusher failing their stealth rolls means that they were detected before they were within melee range.

Another issue is, just because the person on watch detected them, doesn't mean that they know that they were detected. In a real world situation, the ambushing party usually learns that they were detected only when the guard raises the alarm. It is unclear from your description whether you were asking if the character on watch could warn their party or not. Again, I would rule that they always could, because otherwise why are we making these rolls and checks? In this situation, the party might respond slowly to the alarm, but the guard at least is already past any "surprise" or poor initiative.

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    \$\begingroup\$ This is the most important part from my perspective. "just because the person on watch detected them, doesn't mean that they know that they were detected." The bullywugs have no reason to roll initiative when they think they have the drop on the party. The guard, as an instant response, should have ample time to shout an alarm to his sleeping companions. \$\endgroup\$ – Carson Jun 6 at 15:29
  • \$\begingroup\$ This seems to be the exact same two points I raised in my reply. It's tough but helpful to read every answer first. Often I'll see one close-enough to what I would write -- maybe not written the way I would -- and simply add a comment. \$\endgroup\$ – Owen Reynolds Jun 6 at 16:13
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    \$\begingroup\$ Compared to previous editions, 5e is very vague about "how far away were they when they were detected?" There is a lot of onus on the DM to make good decisions about this. \$\endgroup\$ – Kirt Jun 6 at 18:25
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This is just an alternative answer, because I really like the existing ones.

If you decide you want to start combat immediately after the stealth vs perception check, I would still rule that the watcher can - if they choose to - yell to wake up their comrades as soon as they spotted the enemy. Two reasons why:

  1. Speaking outside of your turn is not specifically disallowed, and even if rules are interpreted that way, lots of tables allow some out-of-turn speaking. So I don't think a yell at the start of combat would be too bad.

  2. I would house-rule that "being on watch" means you prepare (ready yourself) to do something once you spot a threat (a trigger). It's not technically a ready action (because you can't do that out of combat) but I would rule that it acts like one, and so the watcher gets to yell as a reaction.

However, in order to still give some meaning to initiative, I would argue that the sleeping players will be prone (they were lying down) until its their turn in the initiative order.

This is important if we in fact rule that sleeping is similar to unconscious (at the very least the spell "Sleep" implies as much), because it means that waking immediately saves them from getting auto-crits, but not necessarily from the effects of being prone.

In other words, I see three scenarios:

  • The watch doesn't spot the enemies: The other players are still asleep. Enemies who get in during the "surprise" round, might melee attack sleeping players and get advantage (due to prone) and auto-crits (due to asleep)
  • The watch spots the enemies, but the sleeping players roll a low initiative: The sleeping players wake up from the watch's yell. They are now only prone. Enemies who are first in initiative order might melee attack the prone players and get advantage, but no auto-crits.
  • The watch spots the enemies, and sleeping players roll a high initiative: The sleeping players wake up from the watch's yell. They get their turn in initiative and use half a movement to get up. Both the advantage and the auto-crit from melee attacks have been averted.
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  • \$\begingroup\$ Saying that sleeping players are prone seems redundant. Who thinks they aren't? As for a readied action, being on watch is long, boring, you're tired and aren't expecting trouble (otherwise everyone else wouldn't be sleeping). But your point #1 seems fine. \$\endgroup\$ – Owen Reynolds Jun 8 at 16:03
  • \$\begingroup\$ My point about being prone is that they might wake immediately (no longer unconcious, no longer getting auto-crit) but don't stand up immediately (still prone). I wanted to point out that waking can occur before combat, but getting up would first require their Initiative. \$\endgroup\$ – RHS Jun 8 at 16:13
  • \$\begingroup\$ So, your point is: the bonus for making perception is everyone else isn't asleep, merely prone. You might clarify that? But there's no official rule for "sleeping", so you'd have to weight in. \$\endgroup\$ – Owen Reynolds Jun 8 at 19:32
  • \$\begingroup\$ I was ("yes and") building on OP's own ruling/assumption that sleeping is like unconcious. \$\endgroup\$ – RHS Jun 9 at 5:58
  • \$\begingroup\$ I elaborated in my answer. I hope it's now clearer. \$\endgroup\$ – RHS Jun 9 at 11:52

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