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Message: <blockquote data-quote="Theo R Cwithin" data-source="post: 5282580" data-attributes="member: 75712">Personally, I'd just roll a single Listen check for the entire unit of guards, perhaps using the "most attentive" guard's Listen ranks, with +1 or +2 for each additional "somewhat attentive" guard.  This minimizes rolling by treating the check as a single unified encounter,  but still allows you to give a little character to the guard unit: is it 5 guards, 4 of them throwing dice and not paying attention and only one "serious" one; or are they all alert and focused on listening for intruders.For multiple PCs sneaking, I'd have each PC make his own Move Silently check against the entire guard unit's "Listen" skill, as described above.  The game is focused on the PCs, and success or failure of each one should be more or less independent of each other.I think any extra noise that masks the PC's own noise (eg, wind, guards' conversation, etc) is a circumstance penalty on the guards' group Listen check (rather than a bonus on the PC's Move Silently check).  I don't know that it makes a huge difference, but it might in some cases, so I'd be sure to think of it this in case it matters.The important thing in cases like this, IMHO, is just to be consistent.  Whatever you decide, just make sure it's run the same way each time so the players have an idea how to approach such situations.</blockquote>