If a character trips or otherwise falls prone into a square covered in caltrops, would he or she be susceptible to damage from multiple caltrops? Stepping on one assumes just one caltrop, one attack roll, one point of damage. How would you resolve landing face-first into a pile of them? Multiple attack rolls? A damage roll? Percentile? Could they get through thick armor? Would a small creature suffer less damage because of less surface area?
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Actually stepping into a 5 foot square covered in caltrops is the one attack and 1 point of damage. A character tripping in a area of caltrops shouldn't be in any danger of extra damage by the RAW. Of course you could house rule that they do a single point of damage, but don't affect anything else. It's a nice bonus for a Player who actually uses some Caltrops effectively (which I don't see very often).
--Solid as a Vrock!
I would say a potential 1d4 in damage would be sufficient. Stepping into an area with caltrops is one thing, but actually falling into it you are potentially exposing more surface area with which to have the annoying things stuck into you.
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This happened in a game I played in. We had some people cornered in a cabin, and they were waiting for us to come to attack them. Me (a rogue) and the other rogue dumped out a bunch of caltrops in front of the door while one of the other members of the group went around the side and threw an alchemist's fire with a bunch of smokesticks strapped to it into the building through a window. Whenever they ran the risk of suffocating, they ran out of the front door (the only door), where upon we (me and the other rogue) pulled a rope taut and tripped both of the bandits that ran out. The DM never actually told us how much damage it was, but after we jumped on them to get across (thus making them take the damage again) they didn't try to get up.
Also, I put two bags worth of caltrops in that one 5 foot square. Ugh, thinking of it realistically there are so many bad things that could happen from falling onto a pile of those. When it's just your foot I can see why it's only one point, but when your whole body is exposed to them they can actually reach much more vital areas. After all, you only need to go an inch deep to do massive damage, and they are completely capable of doing that.
I'd say 1d6, equivalent to a normal fall from 10'. I would say more, because of how damaging that actually seems, but for balance purposes 1d6 seems sufficient.
This came really handy, I'm gonna coat mine in poison. :)