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There is a player in my group whose character is developed around staying in trees, climbling, Athletics, Acrobatics, and such. He likes to climb trees and then leap down onto enemies from the tree branch in the beginning, but how should this be properly handled?

According to rules, he should take fall damage for falling off 10+ feet onto an enemy, but I consider the fact he is skilled in doing this as per his background.

There is no actual skill that he has that says he would nullify fall damage or instead apply it to the enemy, or that he should gain any benefit from this action.

Should I simply give him advantage on the attack roll, ignore fall damage, and call it a day?

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    \$\begingroup\$ Also, Welcome to RPG.SE! Take the tour if you haven't already and see the help center or ask us here in the comments (use @ to ping someone) if you need more guidance. Good Luck and Happy Gaming! \$\endgroup\$ – Someone_Evil Nov 16 at 18:41
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    \$\begingroup\$ What level is this PC? \$\endgroup\$ – KorvinStarmast Nov 17 at 15:11
  • \$\begingroup\$ @KilrathiSly This looks like the core of an answer. \$\endgroup\$ – KorvinStarmast Nov 25 at 13:43
  • \$\begingroup\$ actually this should have been a comment to the Allan Mills answer. wrong place. I'll move it. \$\endgroup\$ – KilrathiSly Nov 30 at 15:16
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The problem is this part of the falling rules:

The creature lands prone, unless it avoids taking damage from the fall.

You are suggesting you give the PC advantage on the attack and no damage when they really should be landing prone after taking damage.

The question then is whether negating the damage is fair or not. The problem with the falling rules is they don't consider what you land on. If you fall 30 feet and land in a deep pool of water then your damage should be reduced or negated. For this example it's a matter of how you land in the water. A clean dive or a pin drop would be the ideal way of landing, a belly flop would be the worst.

Landing on an opponent would follow similar logic. Unless they are dropping on something hard like a golem their opponents body should be usable to break their fall a bit.

I'd suggest making the PC roll an acrobatics check to land on their opponent correctly. Have the DC determined by distance fallen. If they fail then they and their opponent take damage and they don't get their attack.

Do keep in mind the distance between the attacker and the target. If they are 15 feet up in the air on a branch and their opponent is 6 foot tall then that is only 9 feet.

If they drop too far you might want to consider a roll (athletics maybe) to jump on their opponent accurately.

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  • \$\begingroup\$ When considering the target's height, you should probably only count up to their shoulders. Their head might get hit, but it's not going to break your fall much. \$\endgroup\$ – Ryan_L Nov 18 at 6:28
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    \$\begingroup\$ @Ryan_L: I'd hazard a guess that any creature with a non-negligible height difference between its shoulders and its head to have a fairly big/sturdy head and would actually break your fall similarly to a humanoid's shoulders. \$\endgroup\$ – Flater Nov 18 at 9:55
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    \$\begingroup\$ @Ryan_L Given that this is D&D, it's probably simplest to just do the math based on the five-foot cube that a medium creature controls. \$\endgroup\$ – Admiral Jota Nov 18 at 18:12
  • \$\begingroup\$ Always use caution when houseruling changes to fundamental rules. This change of removing the damage from the fall is a fundamental change that breaks many of the game mecanics and thus allows your player PC to be way stronger than he should be with this tactic. The fundamental rule is you fall 10+ feet you take damage and land prone unless you have a feature or magic to avoid such damage. The character jumping on a creature from over 10' should likely cause damage to the target creature (there is a rule for falling objects in Xanathar book) but also take damage himself and land prone \$\endgroup\$ – KilrathiSly Nov 30 at 15:16
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The trick here is he is trying to get a mechanic, (a class feature) for free. There are ways to mitigate falling damage so you could do this.

Slow Fall
Beginning at 4th level, you can use your Reaction when you fall to reduce any Falling damage you take by an amount equal to five times your monk level. (PHB, Monk, p. 78)

Monks get a class feature to mitigate falling damage; there are spells like feather fall that also reduce or eliminate falling damage.
Without these he takes falling damage by the rules.

Contrary to what movies portray, hitting a person is not really going to save you so unless you are going for a very cinematic style there is little reason to allow it.

As a DM I would have no problem with a person jumping out of a tree to surprise, getting the attack, but also taking the fall damage; they can attack in the air before they hit.

Alternatively, you could create a home brew feat that lets them mitigate a small amount of fall damage, or craft is so that it is similar to the monk class feature.

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  • \$\begingroup\$ Hitting a person can save you. The think is, that hitting anything will allow you to change the direction of the fall, that is convert the vertical fall into a sideways fall, thus reducing the vertical force. Also, a standing body will not fold immediately and it will reduce your falling speed slightly, not even speaking about the reduction of the fall height. In summary, if you can safely fall for 2 meters, hitting somebody will increase "safe" falling height to 4 meters at least. If you hit. \$\endgroup\$ – Sulthan Nov 18 at 7:44
  • \$\begingroup\$ @Sulthan While that is true, enemies with pointy or sharp limbs or equipment may well increase the damage. In addition if your weapon literally ricochets off an armor then you risk falling into it. \$\endgroup\$ – user3819867 Nov 18 at 14:33
  • \$\begingroup\$ @user3819867 True. In my opinion hitting the target is something that's much more difficult than people would expect. \$\endgroup\$ – Sulthan Nov 18 at 14:39
  • \$\begingroup\$ @Sulthan hitting an irregular object does far more harm even with a slightly reduced distance than hitting the ground feet first. it gets infinitely worse they and/or you have weapons and armor. \$\endgroup\$ – John Nov 18 at 14:42
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Backgrounds aren't built to provide mechanical combat features

Should I simply give him advantage on the attack roll, ignore fall damage, and call it a day?

If you did that, your PC is doing something like "Slow Fall" which is a class feature (4th level) of a Monk and, when you offer advantage, is getting part of the Assassin (Rogue) archetype from 3rd level. (Assassinate, p. 97, PHB)

In short, no, you should not do that unless you are offering the other PC's a similar 'free' class feature. But, as you are in home brew territory, there are a number of things that you can do.

"It's a part of his background"

Review the backgrounds in the PHB. How many of them provide a tactical mechanic? Spoiler

none of them do. :-)

You can customize a background, but be careful with mechanical combat features if you do.

To customize a Background, you can replace one feature with any other one, choose any two Skills, and choose a total of two Tool Proficiencies or Languages from the sample Backgrounds. You can either use the Equipment package from your Background or spend coin on gear. Finally, choose two personality traits, one ideal, one bond, and one flaw. If you can’t find a feature that matches your desired Background, work with your DM to create one. (PHB p. 125)

Background features include: free/working ship passage(Sailor), guild membership(guild artisan), criminal contacts(Criminal), false identity(Charlatan). Travel Movement bonus (Marine, Ghosts of Saltmarsh)
None of these includes a combat mechanic.

Homebrew of a feat looks like your best way forward here

Take a look at the combat feats in Chapter 6 and tailor one that fits.

  • Homebrew feat examples; outline;
    • "Tree Fighter"; (1) reduces falling damage by half when making such an attack, (2) granting a bonus on initiative, and (3) perhaps one other benefit like advantage on Stealth checks in the trees ...). This is similar to the feat Skulker, but different.
    • A feat that more or less replicates the Monk Slow Fall class feature and perhaps advantage on Stealth checks

Homebrew an archetype/sub class

This is a bit more work, but you can rebuild a Rogue/Fighter/Barbarian/Ranger sub-class from the bottom up to fit this character concept. A couple of examples are here, and the entire series of unearthed Arcana articles include class and sub-class modifications. I'd recommend that you and your player work together on such a creative process. (My nephew built a "Water" Domain cleric with our DM a couple of years ago. It worked out well).

RAF/Big picture question: the campaign - how much is in forests?

For how long is "fighting in trees" a part of your campaign? If most of your campaign is out of doors and in forests, fitting this "tree fighter" bit becomes important for as long as your campaign lasts: to level 6, to level 10, to level, 15, etc.

If, on the other hand, this situation comes up only now and again in play, but most of your campaign is in cities and dungeons and at sea, then substituting in a modified class feature from the background may fit. For example, for this narrow application, reducing this character's falling damage by 1d6 if they are attacking out of trees like that is an occasional benefit, and it doesn't negate the damage usually taken from such an attack. In certain situations this character has an edge, but in most others they are a (whatever class they are).

That last approach is based on "Rules as Fun" more than "Rules as Written" as an approach, but it is a way to proceed.

RAF. Regardless of what’s on the page or what the designers intended, D&D is meant to be fun, and the DM is the ringmaster at each game table. The best DMs shape the game on the fly to bring the most delight to their players. Such DMs aim for RAF, “rules as fun.” We expect DMs to depart from the rules when running a particular campaign or when seeking the greatest happiness for a certain group of players.

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