Can I spam caltrops by dropping a basket full of them from altitude?

Question

Caltrops reads:

As an Action, you can spread a single bag of caltrops to cover a 5-foot-square area. Any creature that enters the area must succeed on a DC 15 Dexterity saving throw or stop moving and take 1 piercing damage. Until the creature regains at least 1 hit point, its walking speed is reduced by 10 feet. A creature moving through the area at half speed doesn't need to make the saving throw.

D&D Beyond suggests that the aforementioned "bag" is 20 caltrops, which cover a five-foot square. But, what if I put 100 caltrops in a basket and had my imp familiar drop it from 100 ft in the air? Would the impact spread them over an area lager than a five-foot square without any expenditure of action economy?

If so, how would this play out? A relevant scenario might include a 15ft pinchpoint (cave entrance, portal, etc) that enemies are pouring through.

---

Edit for additional consideration: The idea is, PC purchases 5 bags of caltrops in town and dumps them into a basket. PC gives the basket to a flying creature, whom carries it until the encounter takes place, then ascends to Xft to drop the basket.

This is mechanically similar to spreading 5 bags of caltrops across an area, outside of initiative. However, it is more powerful because it allows players to make decisions with more information.

---

Do caltrop penalties stack? does not answer this question, which concerns action economy and item usage rules—not stacking penalties.

Answer 1

You likely need an action per square

It has been established that the damage of caltrops is unlikely to stack if you drop more caltrops on the same 5-foot-square area.

I think by a strict rules mechanic reading, the only bag on the equipment list is the bag of 20, and the only action offered by it is:

As an Action, you can spread a single bag of caltrops to cover a 5-foot-square area.

There is no bag of 100 on the equipment list, so how that would be handled will be up for your DM to decide. See Tasha's Cauldron of Everything, page 4, on situations not covered by the rules:

The rules of D&D cover many of the twists and turns that come up in play, but the possibilities are so vast that the rules can't cover everything. When you encounter something that the rules don't cover or if you're unsure how to interpret a rule, the DM decides how to proceed

While you can make a real world analogy based case that a larger bag shaken out from higher up should scatter to a larger area, D&D is not a physics simulation, it offers a game system with mechanics designed for speed of play and balance.

The action cost to spike a five foot square serves to create a balancing point that keeps you from spamming the effect -- for example, you could argue that turning over a bag of caltrops could be considered an object interaction, so you should be able to use your free object interaction to empty one, too, and the action cost blocks this.

If I were to adjudicate it, I therefore would rule that if you dumped a bag of 100 in one action, they would end up in the same 5-foot square. Only if you took care to shake it out over five different squares using five actions, you could cover 5 squares. But talk with your DM - they might decide differently.

Answer 2

It depends what your GM rules in the particular context where you used them.

My gut instinct is that if you dropped 100 caltrops from 100' in the air, you're not very likely to get 5 neat squares with dense and well-scattered caltrops, and none of the caltrops outside those squares (which is what you would get if you spent the 5 actions scattering caltrops from 5 bags into 5 squares).

My guess is that you'd be far more likely to get one or two "overdense" squares and maybe 10 squares where there are some caltrops, but not densely enough to make it likely that someone just passing through the square would step on one unless they're careful. Or maybe they all bounce too much and you end up with a very wide area of caltrops insufficiently dense to demand a save. Especially if the ground is hard (like rock), I'd think they would bounce a lot more. And if the ground is too soft and they're falling too fast when they hit, some of them might stick into the ground point-down, becoming near useless.

There are plenty of ways to rule that this doesn't work based entirely on the logic of the situation, without even considering whether a GM thinks this tactic is an "exploit" that shouldn't be allowed.

This is not a rules question.

The rules provide one way you can apply caltrops and get a specific mechanical effect (requiring a save if anyone enters a specific square). If you do anything else with them, you're asking your GM to describe what would happen (and how much time/effort it would take, translated into actions), just as if you do anything else with any other object for which there are no specific rules. The rules simply don't say what happens if you tip out a bucket of caltrops 100' above the ground, but it's an action that can physically/logically be performed, so it's up to the GM what actually happens in the world.

As such there is no "right" answer here. What happens at your table when you try this depends on the GM at the table, not on what people on rpg.stackexchange.com say. You could get a clear answer saying "Yes this would work" with thousands of upvotes, lots of anecdotes of people saying "yeah, I do this with caltrops all the time in my games", and your GM would still be perfectly within their rights to rule that it doesn't.

If this is the first time you've tried this and your GM wants to reward clever thinking, it's probably more likely to work. If you try this a lot and/or your GM doesn't like giving items that have specific rules for using them any more flexibility/power than is conveyed by those specific rules, then it's probably less likely to work.

If you want this trick to work as an ordinary combat tactic that you intend to rely on, you should have a chat with your GM between sessions and make sure they're on board with it.

Answer 3

Allowing this creates a number of issues

To address your question which you have clarified in the comments

What I want to discuss is, how to define a working model for how to adjudicate a technique like this. Does it create balance issues or "pull on threads" with respect to other parts of the game. (For example, can I do this with Alchemist's Fire? Acid? Holy Water? Bombs?

Yes, this pulls threads and creates untenable issues. For example:

• Filling a large net with flasks of Alchemist's fire logically allows you to firebomb an entire area
• Filling a large bottle with poison, instead of a small flask, should let you cover a large amount of ammunition with poison in a single turn
• By braiding three pieces of rope together, you should be able to increase the strength save DC to break out of it.
• Filling a bucket with oil should let you splash it over a much larger area than a 1 pint clay flask

etc.