Death From Above

Levels 5-10

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As the party travels through a desolate stretch of road in a dark forest, they are ambushed from above. Deadly arrows rain down as the party is taken unaware. Will they survive this lethal ambush?


In a certain forest on the edge of civilization, the brush grows thick and dangerous guerilla forces train in the shadows of tall trees. This part of the forest is known for those mighty trees, reaching a hundred feet or more into the air (or higher, if that’s what your game is like). The lowest branches are forty or fifty feet off the ground and thick as tree trunks in their own right. At dusk, it can be nearly impossible to see shadows crouching on the branches with arrows nocked to the strings of their long bows.

Run this encounter when the party is passing through a stretch of wilderness. As always, we’ll adapt the encounter to suit the needs of your game by tailoring it to advance or respond to one of the party’s goals. I’ll often use an encounter like this to introduce a new faction or character into the game, so consider if there’s anyone you need to introduce before picking your encounter below. More advice on that in the “Goals” section.


This encounter happens when the party is traveling on a forest road, ideally at dusk (for thematic purposes—darkvision is too accessible to make building this encounter around vision worth it). When the party wanders into hostile territory, or when someone fails a check to navigate or sneak through the forest, the enemies attack!

This encounter involves a group of enemies with powerful ranged attacks in the trees above the party, raining down arrows and spells from a safe distance. This encounter is theater-of-the-mind, and movement works like this:

  • All combatants can use their move action on their turn to take cover from ranged attacks (behind a tree, against a branch, etc). Characters who end their turn like this get a +5 bonus to AC against ranged attacks until the beginning of their next turn.
  • All combatants can climb with a DC 15 Strength (Athletics) or DC 15 Dexterity (Acrobatics) skill check, but it will take four move actions (remember you can use your standard as a move) to reach the level of the branches—long enough that it’s an nuisance to do so. Climbing down takes half as many move actions.
  • Combatants up in the branches can jump to the branch of another tree on the other side of the road by making a DC 20 Strength (Athletics) or DC 20 Dexterity (Acrobatics) check. If they fail by fewer than five, they stay where they are, but if they fail by five or more, they fall to the ground below.
  • Combatants who fall from the top take 6d6 damage. Characters who fall while climbing take only 3d6.

Assume that all characters are in range of an attacker’s ranged attack for convenience. Thrown weapons might be out of range for attackers on the ground, depending on your call as DM.



The Guerillas are the main enemy in this encounter, and the only one we’ll discuss. They want the party out of their woods, and they’re not afraid to kill to get their way.

Pick a faction from your game that might attack the PCs in the forest. such as a group of rangers who are distrustful of outsiders or a group of murderous monsters.

  • Encounter A features a group of rangers looking to defend their part of the forest. Is there a faction in your game affiliated with the natural world?
  • Encounter B features a marauding group of monsters with a grudge against the “civilized” world. Is there a faction in your game like this, or who might hire monsters like this?
  • If you don’t have either one of those, pick a faction who might hire someone to hunt the PCs and use Encounter C (where mercenaries stage the ambush).

How far is this faction willing to go to pursue the PCs? How hard will they fight if the fight isn’t going well and their comrades start to fall?

Using These Encounters

Who have your players wronged lately? Why might they face an ambush in the woods? You can use bandits (Encounter C) if no one comes to mind, but they you should ask yourself why your party isn’t getting into trouble. They need to get into more trouble!

  • If your party has harmed a natural feature lately (like burned a forest or grove, or polluted a body of water), run Encounter A.
  • If your party contains a member of an uncommon race (such as dragonborn, tiefling, etc), run Encounter A.
  • If your party is formally aligned with a nearby government, run Encounter B.
  • If your party has a religious member who wields divine power, such as a cleric or a paladin, run Encounter B.
  • If your party has wronged an urban faction lately, or you’re not sure what to do, run Encounter C.

This is a tough encounter all around because the party is at a range disadvantage. Make sure to emphasize the importance of taking cover from the ranged attacks coming from above. Of all the encounters, Encounter C is the deadliest.

Encounter A

Travelers in these parts know to fear the woods at dusk, when many creatures of the forest are on the hunt.

Setting up this Encounter

This encounter is an ambush by a group of zealous elf rangers, eager to punish the group for trespassing on their territory. Their attack has religious undertones, whether that’s retribution for a natural feature the party damaged recently or on behalf of a slighted druid or natural spirit. The rangers might also be suspicious of a party member of an uncommon race and wish to drive the unwelcome character away, or worse.

All this means the rangers will announce themselves before they actually attack, but after they’ve gotten into position. Describe how the shadows lengthen as the party makes their way through the wood, and how they can tell this is a wild place despite the road winding through it. On a DC 15 Intelligence (History) check, perhaps a character remembers a certain group of rangers that are sworn to defend this part of the woods. If they’re making camp, describe how the pack animals, if they have any, are at ease, but the characters feel like someone is watching them. On a DC 20 Wisdom (Perception) check, reveal that shadowy forms in camouflage cloaks are watching them from the branches above.

When the time is right, or just before the players are about to act, the rangers call out from the shadows above. Have them declare that the party is trespassing on their territory, and they are unwelcome. Make it clear that this attack is either retribution for the the action the party took, or is a racist response to the party’s composition.

Do this before rolling for initiative! Give any party member who passed the Perception check above but hasn’t acted on it yet the chance to act or prepare. If they can’t think of anything to do, give them +4 on their initiative bonus if this encounter becomes a fight.


For this encounter, use a number of guerilla fighters equal to the number of players.

Concealing Cloak

Once in this encounter, a Guerilla Fighter who makes a successful Dexterity (Acrobatics) check to jump tree branches becomes hard to see in the darkness. They can reroll their next attack against an opponent on the ground that misses the target’s AC, but is higher than the target’s passive Perception.

This starts as a social encounter, but not a friendly one. Anyone can see that the rangers in the trees above have arrows on their bow strings, though the bows aren’t drawn… yet. In this social encounter, the Guerillas communicate:

  • The party members shouldn’t move or go for their weapons
  • The party shouldn’t cast any spells

If they do either of these things, have them roll for initiative and the fight starts. The Guerillas get a +4 bonus to initiative for being ready to fight.


  • The party must be held accountable for their trespassing and their other offensive actions
  • The typical penalty is death, but perhaps a deal can be struck

Let this conversation play out as much as you’d like. Most parties will want a fight here, but not all will. Use your knowledge of the faction in your game that either hired the Guerillas or that the Guerillas are from to decide how they react to the party’s counter-proposal.

In this fight, the Guerilla Fighters gain the Concealing Cloak ability.

Resolving this Encounter

Concealing Cloak

Wondrous Item, uncommon.
While wearing this item, the wearer may tell the group about how their character is concealed from view by the cloak’s camouflage. If the group (and the DM) accepts their explanation, the wearer may reroll their next ranged attack against a target that misses the target’s AC, but is higher than the target’s passive Perception. If the group decides the camouflage would work very well (maybe it’s in a forest of the same type and coloration as the cloak), they make the reroll with advantage. This ability has one charge, which is expended when the reroll is made. It recharges when the wearer rolls for initiative.

If this encounter resolved without violence, think about what message that sends to the faction that sent the Guerilla Fighters. What would the consequences be? Telegraph this to your group.

If the group defeated the Guerilla Fighters, think about how the faction that sent them might take that. Would they redouble their efforts? Back off for a while? Try to parley instead? Or just forget about the whole thing. Telegraph this to your group by speaking as one of the Guerilla Fighters right before they expire.

If the Guerilla Fighters were defeated in battle, they conveniently left behind just enough Concealing Cloaks that each party member can have one.

Encounter B

In the darkest places in this close wood, there are as many dangers in the trees above as there are that prowl in the shadows below.

Setting up this Encounter

This encounter features a group of marauding goblins and hobgoblins that ride spiders through the dark wood, searching for easy prey. These raiders will instinctively attack anything that reeks of civilization, but they might have a special eye out for your party. They’ll target religious figures, local government, agents of the crown, and anyone else who represents a threat to their corner of wilderness.

Use this encounter when you want to signal a group’s strengthening relationship with the forces of civilization in your world. The monsters attack because they sense your group’s alignment with powerful forces that oppose them, and they’re traveling alone—the perfect target for this band.

As the party ventures deeper into the woods, describe how the shadows grow darker and the atmosphere becomes more oppressive. The path before them is eerily quiet, as if even the wildlife has fled the area. On a DC 15 Intelligence (History) check, a character may recall tales of goblins and hobgoblins in this region, known for their ruthless tactics and giant spider mounts.

If the party is making camp, describe how their pack animals, if any, are uneasy and skittish, sensing danger lurking nearby. The party hears skittering and whooping in the distance, growing closer as it moves through the canopy. Any PC who pays attention will see goblinoid figures on giant spiders mounts moving quickly through the canopy on hairy legs. The battle cry starts as soon as the PCs are aware of the goblins, and then both sides roll initiative.


In this encounter, use twice as many Guerilla Fighters as players. Two more enter the fight each round, until they retreat (described on right).

Giant Spider Mount

The Guerilla Fighter can move along sheer surfaces, but not ceilings. Critical hits against the Guerilla Fighter can optionally kill the giant spider mount instead of dealing damage, causing that Guerilla Fighter to lose this ability and fall to the ground.

(Optional Rule): The Guerilla Fighters use specially crafted arrowheads, a fusion of goblin cruelty and hobgoblin industry. These arrowheads are barbed and cause heavy bleeding. Any character that takes damage from the Guerilla Fighter’s ranged attack heals only half the normal healing value from all healing sources except 3rd-level or higher spells. After receiving healing from a 3rd-level or higher spell, the healed character is immune to this effect for the remainder of the fight.

The monsters attack in waves, with more guerilla fighters arriving each round until the total has been reached. At the beginning of each round, describe how a number of Guerilla Fighters have entered arrow range.

The monsters are cowardly and will attack from the trees above, raining arrows down on their foes until everything stops moving. They’re here to kill the party, not to treat with them, so they won’t stop firing while they have the upper hand. If for some reason a Guerilla Fighter is disarmed, they’ll retreat and watch from a distance.

The Guerilla Fighters are cowardly and not eager to die here. After a number of Guerilla Fighters equal to the number of party members have been killed, no more Guerilla Fighters enter the fight. Remaining Guerilla Fighters flee when they reach half health, or when they are outnumbered by the party.

The giant spiders are just mounts and don’t have a turn in the initiative order. Instead, the Guerilla Fighters gain the Giant Spider Mount ability.

Resolving this Encounter

The Guerilla Fighters in this encounter aren’t carrying much in the way of loot. Characters who search the scene should find clear evidence tying this group to the faction you chose in the setup. A letter is traditional, but it could also be a special marker, coinage only carried by certain members of that faction, or a piece of identifying jewelry or clothing. Telegraph to the group that this ambush was a response to their alignment with the forces of civilization.

Characters who wish to recover some barbed arrows from the scene gain the following item:

Barbed Arrows

Wondrous Item, uncommon
These arrows are crafted with wicked barbs that make them difficult to remove and heal. Characters who possess this item may choose to use these arrows in place of their normal ammunition in their longbow or shortbow. Enemies who take damage from ranged attacks made with these arrows receive half the normal amount of healing from all sources except spells of 3rd level or higher. After a fight in which a character uses these arrows, the character should roll 1d20. On a 5 or less, the arrows have all been used and no more can be recovered from the battlefield.

Encounter C – KILLER

Monsters lurk in these woods, but the most dangerous hunters in these parts are men, and the most dangerous game is…

Setting up this Encounter

This encounter features a coordinated attack on the party by a group of experienced mercenaries. More so than the other encounters, this one features a capable group who is trying to kill the party. This might be a group of hardened mountain bandits, looking for a big payday, but it might also be a group of assassins hired by an enemy of the PCs. The party won’t know this when the attack happens, but we’ll give them an opportunity to discover who has it out for them after the fight’s over.

Use this encounter when the party travels through a place far from civilization, where help is far away and no one is likely to hear the fight. These enemies are professionals and will try to surround the party as they sleep at night, then attack with overwhelming force and end the fight quickly.

Wait until the party rests for the night, then have the party member who is keeping watch roll a DC 15 Wisdom (Perception) check to notice the encirclement. If no one is on watch, then have the whole party roll a DC 25 Wisdom (Perception) check.

As soon as the roll is made, success or failure, describe how the night suddenly transforms into a choking, coughing mess and the fight begins—roll for initiative!


For this encounter, use as many Guerilla Fighters as you have players.

Smoke Bomb

As a standard action, the Guerilla Fighter lobs a small package that explodes in a flash of smoke and choking fog. The Guerilla Fighter makes a ranged attack (+8 to hit, range 30 ft), but instead of dealing damage, the target must make a DC 14 Constitution saving throw. On a failure, all other creatures become invisible to the affected creature until the beginning of their next turn. On a success, the effect still happens, but can be ended by using a reaction to move out of the smoke (this moves a character who is in cover into the open).

The fight begins with one of the Guerilla Fighters tossing a smoke bomb into the party’s camp. Any character who passed the Perception check can choose to avoid the smoke bomb, but everyone else is caught in the effect. If the character on watch warned the party verbally, they gain advantage on their saving throw against the smoke bomb effect.

Each turn, the Guerilla Fighters will focus their ranged attacks on the party member they judge to be the biggest threat, starting with the party member on watch. Each turn, the first Guerilla Fighter to act will throw a smoke bomb at their current target. Narratively, each one only throws one bomb (they only carry one each).

Decide before this encounter how punishing you want to be with sleeping arrangements—do your party members usually sleep in their armor? If not, it takes a long time to put on, longer than they have in combat. Party members woken by the initiative roll start prone.

This encounter has the potential to be killer. Don’t make it harder than it needs to be—give your players the victory they earn. If they are all defeated but you don’t want the game to end, consider having the fight continue as one of the Guerilla Fighters comes down from the trees to inspect the party and confirm they’re dead: this can become a social encounter or you can give each PC a combat action to make things dramatic.

Resolving this Encounter

Smoke Bomb

Wondrous Item, uncommon
Make a ranged attack against a target within 30 ft. Any character who regularly uses throwing weapons, plus rogues, get proficiency with this attack. On a miss, nothing happens. On a hit, the target must make a make a DC 14 Constitution saving throw. On a failure, all other creatures become invisible to the affected creature until the beginning of their next turn. On a success, the effect still happens, but can be ended by using a reaction to move out of the smoke (this moves a character who is in cover into the open).

Parties who survive this encounter should be amply rewarded in three ways:

  • 2500gp in coin and valuable gems carried by the assassins, equaling part of the pay they were given as an advance on this job. Perhaps the rest is stashed somewhere nearby and can act as a hook towards a certain location?
  • One smoke bomb per Guerilla Fighter who did not throw one.
  • Evidence tying this group to an enemy faction. This is usually whoever hired them, connecting the assassins to a known force. If you’re really devious, this evidence can be fabricated and frame a different faction instead, but allow a skill check to determine that.