Spoiler: OOC: Battlefield Info
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Will be trying a mapless approach for this one.
Approximate ranges between areas are given. Those within a given area are all within movement range of one another unless they seek a specific position somewhere using greater movement speed. Characters may engage other characters in the same area in melee unless unable for some reason, entering threat range using their movement.

Enemies taking cover will lose cover when engaged in melee by a creature, or by a threatening spell such as Create Bonfire or Flaming Sphere smoking them out.

A ship without a manned navigation and/or propulsion is unable to move effectively. Siege attacks and spells used against a stationary ship hit/fail Dex saves automatically. Characters manning navigation can wield weapons or cast spells with one hand without leaving their position unmanned.

We'll feel out more as we go.

East Cliff: Creatures without a Climb speed treat the ground as Difficult Terrain / ~30 feet from Naval Battle, ~100 feet up / ~180 feet from West Cliff
Sarith: Wither 3, Engaged by Spider B
Nilvae: Dying, 2 Failed
Mr. Spide: Banished
Enemies
Drow Agent Xalith: Dying, 1 Success
Drow Crossbowman A: Dying, 1 Success, 2 Fail
Giant Spider A: Dead
Giant Spider B: Unharmed, Engaging Sarith
Surrendered
Drow House-Mage Ulryn of Mizzrym: Unharmed, Concentrating on Fly, Surrendered
Drow Scout A: Unharmed, Half Cover, Surrendered
Drow Arcane Archer A: Scratched, Half Cover, Surrendered

West Cliff: ~180 feet from Naval Battle, ~80 feet up / ~180 feet from East Cliff
Galdar: Riding Charlotte
Charlotte: Climbing on Cliffside
Allies
Topsy: Damaged, Riding Charlotte
Enemies
Drow Scout B: Dead
Drow Crossbowman B: Dead
Giant Spider C: Dead
Giant Spider D: Dead

The Black Manta (Damaged): ~100 feet down, ~60 feet away from East Cliff / ~80 feet down, ~180 feet away from West Cliff / ~5 feet from Pirate Ship
Faedryl: Concentrating on Create Bonfire under Drow Sailor B's Harpoon Gun
Elara: Bloodied, Twilight Sanctuary (1d6+5)
Borthan: Manning Steering Comms (decides if the ship moves closer or further away, Sailing tool check used for ship's Dex saves)
Derendil: Half Cover
Ront: Tower Shield Half-Cover towards Drow Ships
Turvy: Badly Wounded
Allies
Kuo-toa Sailor A: Unconscious, Stable
Kuo-toa Sailor B: Unharmed, Belowdecks, manning Oars
Kuo-toa Sailor C: Unharmed, Belowdecks, manning Oars
Kuo-toa Sailor D: Unharmed, Belowdecks, manning Oars
Kuo-toa Sailor E: Unconscious, Stable
Kuo-toa Marauder B: Dead
Dr. Donk: Unharmed, Belowdecks, manning Oars
Enemies
Drow Venomancer A: Dying, 2 Failed, 1 Succeeded, Poisoned Weapon
Drow Venomancer B: Dying, 1 Succeeded, 2 Failed, Poisoned Weapon
Giant Spider F: Dead
Drow Hexer A: Dead
Drow Hexer B: Dead
Mini Retriever A: Dead
Mini Retriever B: Dead

The Iron Eel (Undamaged): Underwater, alongside DSHS 2
Allies
Blurg: Unharmed, Manning Steering

Dark Pirates' Duergar Sloop (Undamaged): Stalled Out (no power to engines) / ~5 feet from Black Manta
Allies
Stool: Scratched, Concentrating (Healing Spirit)
Orog Wilder: Near Dead, Vision 5 ft. until Arcane Archer turn, manning Wheel, Engaged by Venomancer C
Orc Deckhand A: Dying, Engaged by Hexer E, sharing space with Healing Spirit (heal 1d6 at turn start)
Orc Deckhand B: Dead
Orog Arbalest: Bloodied, Belowdecks, positioned in Bunker, Engaged by Hexer C
Orog Stonehorn: Unharmed
Enemies
Drow Venomancer C: Dying, 2 Failed, 2 Bleed
Drow Venomancer D: Dying, 2 Succeeded
Drow Hexer C: Damaged, in Bunker, Engaging Orog Arbalest
Drow Hexer D: Bloodied, 4 Bleed
Drow Hexer E: Scratched, Engaging Orc Deckhand A

Drow Slave-Hunter Ship 1 (Enchanted Hull, Damaged, Slowed (Siege attacks have Advantage)): Crow's Nest ~20 feet up
Allies
Dawnbringer: Caught on a railing, Dawnbringer Shining (Disadvantage to Drow attacks on board)
Kuo-toa Marauder A: Lightly Damaged, 2 Bleed, Belowdeck, Recklessly Attacked
Y: Unharmed
???
Jorlan (scarred male drow from Velkynvelve): Dying, 1 Failed
Enemies
Ilvara Mizzrym, Priestess-Commander of Velkynvelve: Dying, 1 Failure, 1 Success
Shoor (Ilvara's lover): Near Death
Asha (Ilvara's junior priestess): Dying, 2 Succeeded, 2 Failed
Drow Elite A: Damaged, 6 Bleed, in the water
Drow Elite B: Damaged, 8 Bleed, in the water
Drow Arcane Archer B: Near Death, 6 Bleed, in water
Drow Wizard: Dead
Drow Crossbowman C: Dying, 2 Success, 1 Fail, in Crow's Nest
Drow Crossbowman D: Bloodied, Sawbladed
Drow Sailor A: Unharmed, manning Wheel
Drow Sailor B: Bloodied
Drow Sailor C: Bloodied, 2 Bleed
Drow Sailor D: Bloodied, 2 Bleed, in water
Drow Sailor E: Bloodied, 4 Bleed, in water

Drow Slave-Hunter Ship 2 (Rudderless, Sunken) Sunken
ALADIN: Belowdeck, Sunken
Enemies
Drow Crossbowman E: Scratched, 2 Bleed, Sunken (removed from combat)
Drow Crossbowman F: Scratched, 2 Bleed, Sunken (removed from combat)
Drow Sailor F: Damaged, 2 Bleed, Grappled by Slave Mob A, Sunken (removed from combat)
Drow Slave Mob A: Damaged, 2 Bleed, Grappling Drow Sailor F, Sunken (removed from combat)
Drow Slave Mob B: Damaged, 2 Bleed, chained belowdeck, Sunken (removed from combat)


Spoiler: Initiative
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With Timing, the naval battle will begin on round 2. Characters on the Manta can currently see the flanking battles, but the enemies above have 3/4 cover from the angle. Characters above have a vantage to fire on characters on the drow ships.

Jorlan - n20

Drow Agent Xalith (Legendary Action) - 23
Ilvara (Legendary Action) - 22
Drow Agent Xalith - 18

Orog Arbalest - 17

Ilvara Mizzrym, Velkynvelve Priestess-Commander - 16

Orog Wilder - 15
Orc Deckhands - 15
Kuo-toa Marauders - 15
Elara/Turvy - 14

Drow Venomancers - 14
Drow Crossbowmen - 14
Drow Sailors - 14

<inhale> Faedryl/Sarith/Nilvae/Spide/Donk/Galdar/Charlotte - 13

Shoor - 12
Drow Scouts - 12
Giant Spiders - 12
Drow House-Mage Ulryn (Legendary Action) - 11
Drow Elites - 11

Kuo-toa Sailors - 10

Asha - 10
Drow Arcane Archers - 9
Drow Hexers & Mini Retrievers - 9

The Iron Eel - 8
Borthan/Derendil - 8

Drow House-Mage Ulryn - 8

ALADIN/Ront - 6
Topsy - 6
Orog Stonehorn - 5
Stool - 4
Drow Slave Mobs - 0

Borthan and Derendil are up, as are Ront and ALADIN!


East Cliff

A well-placed shot ends the life of one of the spiders, but Sarith can see that the half-elf's condition is worsening. The creature rears back and bares its fangs, pursuing Sarith next. He is able to anticipate it, however, and sidesteps with ease. A second ray from above fails to track its movement, freezing over the stone behind it.

The two surrendered drow rush to Xalith's side and attempt to stop her bleeding, to no success.

Spoiler: Combat Log
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Nilvae fails a death save.
Sarith sneak attacks Giant Spider A for 15 damage, enough to finish it off.

Drow Scout A tries to stabilize Xalith, but fails.
Giant Spider B attacks Sarith, but misses.
House-Mage Ulryn shoots another Ray of Frost at Giant Spider B, but misses.
Arcane Archer A also fails to stabilize Xalith.


Naval Battle

As the ships circle one another around the stalled out pirate vessel, Faedryl silently shoves the elite warrior who'd just climbed up back overboard into the water with a satisfying holler, and a splash. Flailing hands try to claw their way up the wet hull, but fail to find purchase as it curves in the water. Her spell exacts its toll this time, causing Shoor to pale as he stands from the dying Ilvara, his hands now shaking with fear.

Running to the harpoons, he steps through Faedryl's lingering flames in order to cut the harpoon line attaching their vessel to the Black Manta. Raising his sword, he points at the sailor manning the wheel, "Turn this ship around! We retreat!" a command his lover would no doubt flay him for... were she to survive.

Pulling himself over the railing onto the remaining drow ship, Y's sawblade reappears in a glimmer of blue light and he launches it into the side of the remaining crossbowman this time. His face is a grim line this time, fully focused on the danger at hand.

Sounds of fighting continue to clamor from inside the pirate ship's bunker, and one of the hexers manages to claw his way back onto the ship. The cursed men show no signs of forfeiting the fight, their souls already damned by fiendish ritual. One of them knocks the remaining deckhand out with another flaming morningstar strike.

Spoiler: Combat Log
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Faedryl tele-bonks Elite B back overboard into the water. He takes 6 fish damage and 2 more Bleed.
Faedryl hits Shoor with Toll the Dead and he fails his save this time, taking 20 damage. He's in rough shape.

Shoor takes 8 damage from Create Bonfire as he moves through it to cut the harpoon line.
Drow Elite A&B try to climb back onto the ship again, but both fail. They take 5 and 3 fish damage and 2 more Bleed each.
Arcane Archer B fails to climb back onto the ship, taking 2 fish damage and 2 more Bleed.
Hexer C gets up, but fails to hit Drow Arbalest.
Hexer D climbs back onto the pirate ship.
Hexer E hits Orc Deckhand A for 11 damage, a KO. Stool takes 6 splash damage, but holds Concentration.

Y's sawblade returns to him, dealing 2 more Bleed to Elite B. Y climbs onto the drow ship and shoots Crossbowman B for 7 damage and a sawblade embed.


Underwater

After dropping Y off on the drow ship, Blurg sluggishly operates the Eel's controls, slithering it down towards the sunken ship.

Spoiler: Combat Log
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Blurg pilots the Iron Eel down near the sinking ship, allowing those in the water to grab hold. ALADIN can also reach the Eel from where he is if he Dashes.