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Jul 25, 2021 at 11:12 comment added enkryptor I don't think this really answers the question. All ability check are up to the DM. The DMG even describes a playstyle when dice aren't used at all, except for a combat. There is nothing special here about Dexterity (Stealth) checks or group checks specifically.
Jul 23, 2021 at 23:45 comment added Charlie Bamford More relevant to the answer: A group of 4 pcs will roll a 5 or below 68.4 % of the time. Regardless of stealth modifier, 5 is likely to be a failure.
Jul 23, 2021 at 23:36 comment added Charlie Bamford Even a party entirely made of rogues will have trouble with group stealth checks where every player needs to succeed. A group of 5 pcs will roll a nat 1 22.5% of the time. Even RAW, this means unless the target isn't worth sneaking up on in the first place, it's not likely to be possible to sneak up on it at all.
Jul 12, 2021 at 19:47 comment added Wyrmwood Good analysis on the impact of using them more often.
Jun 19, 2021 at 3:30 comment added ShadowRanger @Mitten.O: That's not how surprise works in 5E; there is no surprise round, there's a surprised condition during the first round for those caught unawares. It's a little strange if you not being sneaky somehow makes you surprised by the enemies you already knew were there...
Jun 18, 2021 at 20:41 history edited Thomas Markov CC BY-SA 4.0
added 163 characters in body
Jun 14, 2021 at 9:29 vote accept findusl
Jun 9, 2021 at 6:18 comment added Mitten.O I think there is a fourth category: (4) The ones who succeed gain some benefit, or the ones who fail suffer harm. A good example for stealth is when the players are stealthing to ambush. The players that succeed should get a surprise round, the ones who fail, not.
Jun 7, 2021 at 9:15 history answered user56480 CC BY-SA 4.0