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D&D 5E Asymmetrical stealth

I reserve group checks for when the group is actively working together (or they've made a group effort to mitigate their risks).

For example pass without trace on the group would get a group check from me, whereas the group just moving around together does not benefit from that because they've done nothing in particular to enhance their chances.

For a mob of monsters creeping up on the players, I would roll stealth check for each monster and compare that to the passive perception of any PCs keeping watch.
 

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I don’t think it is, since they used the word “stalking.” Sounds like the question is not about ambushing the PCs, but about following them over a long distance and/or period of time without being noticed.

Yeah, that could be so. It's not 100% clear.
 

This. Any PC group trying to reliably surprise their enemies should get the pass without trace spell.

I also really like the Trickster cleric ability to grant advantage to Stealth. That comes in handy for that one player who doesn't know that Dex rules. :)
 

I like what The Angry GM has to say on the matter. I've used this advice successfully in a few campaigns.

Working Together. When two or more characters work together to accomplish the same task, the character with the higher modifier leads the effort. The leader makes the appropriate ability check and enjoys a +2 bonus for one or two helpers or a +5 bonus for three or more helpers. Characters can only work together if it is task where such help is feasible and possible. In addition, a character can only help with a task if they would not be incapable of attempting the task on their own (due to a lack of Proficiency for instance).

and

Group Checks. When several PCs are trying to accomplish something as a group, the GM can call for a group check. First, the GM determines whether the group will succeed if any member succeeds (such as with searching) or if the group will fail if any member fails (such as with stealth). In the first scenario, the character with the highest base Ability Check modifier (Proficiency Bonus + Ability Bonus) rolls the check. In the second scenario, the character with the lowest base Ability Check modifier (Proficiency Bonus + Ability Bonus) rolls the check. Bonuses, penalties, Advantage, and Disadvantage are applied normally to the character rolling the check, but these should only be applied after the GM has determined which player has rolled the check.

For more context: http://theangrygm.com/tweaking-the-core-of-dd-5e/
 




4 mice plus 3 elephants are not sneaky as a group. Accordingly. this is not a situation in which I use group rules. If you have a paladin with Dex 8 in Platemail, you should not be able to overlook his 0 stealth result because his two friends were stealthy.

D&D is an RPG. Characters play a role in a story, and as a DM, we need to think of the game rules in the context of a sensible story. If you think about a sensible approach, anyone failing to be stealthy will raise the guard's attention - so everyone trying to be sneaky must make the roll.

This encourages the PCs, and the monsters, to send the scouts ahead and then bring up the loud folks afterwards. It also discourages trying to send 500 monsters sneakily against the party - it is very hard for them to be that quiet with that many. There is magic that can help, but generally speaking - if you want to ambush someone, you need to be sneaky.

I give advantage to stealth checks when people are not moving. For example, when a bunch of bugbears hide in the bushes along a trail and wait for people to step into their ambush, I give them advantage on their stealth rolls to convey that waiting silently is easier than moving silently.

I also apply a penalty to perception for distance as well. I don't give disadvantage for it: I give a numerical penalty of up tp 10. This allows a fighter in bulky armor to be sort of sneaky at enough of a distance.
 

You know what I hate more than lack of realism? Players setting out twiddling their thumbs cause only those with really high stealth checks explore and scout ahead!

They sit out a whole 1/3 of the game if you play as you described.

4 mice plus 3 elephants are not sneaky as a group. Accordingly. this is not a situation in which I use group rules. If you have a paladin with Dex 8 in Platemail, you should not be able to overlook his 0 stealth result because his two friends were stealthy.

D&D is an RPG. Characters play a role in a story, and as a DM, we need to think of the game rules in the context of a sensible story. If you think about a sensible approach, anyone failing to be stealthy will raise the guard's attention - so everyone trying to be sneaky must make the roll.

This encourages the PCs, and the monsters, to send the scouts ahead and then bring up the loud folks afterwards. It also discourages trying to send 500 monsters sneakily against the party - it is very hard for them to be that quiet with that many. There is magic that can help, but generally speaking - if you want to ambush someone, you need to be sneaky.

I give advantage to stealth checks when people are not moving. For example, when a bunch of bugbears hide in the bushes along a trail and wait for people to step into their ambush, I give them advantage on their stealth rolls to convey that waiting silently is easier than moving silently.

I also apply a penalty to perception for distance as well. I don't give disadvantage for it: I give a numerical penalty of up tp 10. This allows a fighter in bulky armor to be sort of sneaky at enough of a distance.
 

Here is a solution I am considering:

Multiple Characters attempting stealth: one check. Use the lowest proficiency. If more characters lack proficiency in stealth than have it, disadvantage.

If multiple perceiving characters: use highest bonus. If more are proficient at perception than not, apply advantage (or +5 if using passive perception).

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