Quote from Mister_Whisker >>

Harold, dual-wielding his rapier and dagger, attempts to slay Pirate 10 before the man can cut his brother down...

Attack: 7 Damage: 6
Attack: 15 Damage: 4

 'Naut is up!

Going to go ahead and puppet 'Naut again

The armored plasmoid creature will attack Pirate 10 with his pistol

Attack: 12 Damage: 4

Quote from Mister_Whisker >>

Pirate 9, having seen what happened when his companion attacked Emrys in melee, opts to pull out a set of twin pistols and tries to deal with Emrys from a distance.

Attack: 12 Damage: 7
Attack: 11 Damage: 9

Emrys is up!

Updated combat tracker:

Updated maps

His first instinct was to shout to focus on removing the hooks, prevent the pirates from boarding. Then he remembered that his true objective was to lose the fight. They needed the privateers to board, keep pushing the raid and capture the crew. Open-mouthed and ready to shout Emrys managed to contain himself. We still need to look the part, the halfing thought looking at the approaching enemies.

Withy a whisper of incomprehensible words he gathered shadows on his hand, turned them into energy and with eyes dark light the depths of the ocean launched a ray of pure energy and the farthest rope. It was thrown away and the sound of a man meeting the water followed soon. His eyes darted to the tentacle. Maybe it could move one rope. No, he noticed. It is not physical. Instead, he willed it to lash against the closest enemy.

“What? No more melee?” Emrys taunted after seemingly dodging two bullets – he knew that  the attack missing had more to do with the wind and waving of the sea than his or his enemy’s skill. “WE GOT GUEST ON THE STAIRS!” His shout was followed by a murmur. Another Eldritch Blast, another strike from the tentacles. “You won’t run, right?”

Attacks made, Goldenleaf moved into melee range.

Notes: Emrys spends his action to cast Eldritch Blast (26 to hit, 14 force damage) and his bonus action to attack with the Tentacle of the Deeps (14 to hit, 5 cold damage). Both attacks against Pirate 9 (unless he dies with the Eldritch Blast alone. In this case the Tentacle attacks the closes enemy.) He then moves into melee range of the closest enemy.

 

Both attacks hit, but Pirate 9 is still alive (somehow).

Reeling back from the painful assault, Pirate 9 isn't dumb enough to take the bait and charge into melee. He makes two more attacks with his twin pistols, desperately trying to take the down Emrys (or at least break through his icy shield).

Attack: 19 Damage: 2
Attack: 20 Damage: 8

Since no one is around her, Yevelda will spend her turn hurling a javelin at a random pirate on the starboard-side ship (at disadvantage for distance... but the important thing for her right now is to stay angry)

Attack: 9 Damage: 10

William will attempt to cut down Pirate 10 with his twin daggers.

Attack: 19 Damage: 7
Attack: 24 Damage: 6

If either attack hits he deals 2 bonus Sneak Attack damage.

Secret character Initiative: 4
Secret character 2 Initiative: 19

Updated combat tracker:

Areleo and Sayyida are up!

Sayyida raced across the deck to assist William, though they were making a good show of themselves regardless.

Action- Vs Pirate 4 - Attack: 20 Damage: 10 

Sayyida's blade strikes true! Pirate 10 falls backwards, his blood dripping down the stairs.

Areleo unable to control himself he continues to attack Pirate 2

Claw attack 1: 20     Damage: 7

Claw attack 2: 14     Damage: 6

Areleo's two strikes rip the pirate clean open. Disemboweled, he crumples onto the deck.

Sae is up! (Also, I'm going to rule that only a single burning arrow effect will distract the pirates at the same time, so shooting another wouldn't cause any additional delays)

Seeing the pirate that shot at Emrys still standing on the stairs leading up where they are, Sae draws another arrow and sights carefully down the shaft, then lets fly at Pirate #9!

============================

Longbow attack: 10; damage (piercing) 5

Bonus action: Insightful Fighting 19; extra damage if successful 7

Quote from Mister_Whisker >>

Sae's attack goes wide, and the arrow hits the starboard-side ship with a loud thud.

"Hey, watch it you bloody idiots!" a gruff, somewhat familiar voice shouts from across the water.

Harold, meanwhile, attempts to finish off Pirate 10 with two quick attacks.

Attack: 22 Damage: 11
Attack: 24 Damage: 5

Harold's two attacks turn Pirate 10 into Swiss cheese...

'Naut is up!

Updated combat tracker:

I'll just go ahead and puppet 'Naut

The hulking armored creature will go ahead and move up to next to Will and use cure wounds on him, restoring 5 hit points.

Emrys is up!

At the sound of the gruff voice, Sae's left eyebrow rises even higher than her pique at the humiliating miss had already levered it up.  She turns her head enough to call over to Emrys, "Are we acquainted with these pirates, Captain?"

Quote from OisinmacCameron >>

At the sound of the gruff voice, Sae's left eyebrow rises even higher than her pique at the humiliating miss had already levered it up.  She turns her head enough to call over to Emrys, "Are we acquainted with these pirates, Captain?"

 Feel free to make an Insight check if you want to figure out where you've heard that voice before.

The first shot went astray, but the second grasped the head of the halfling. The layer of frost covering his body splattered and his face turned to the ground. Blood ran across his face, a wide grin formed upon his lips while his eyes turned black once again. One step, then another - heavy, loud, almost unbalanced. Emrys walked slowly in the direction of the pirate, closing most of the little distance between the two of them. 

The spectral tentacle lashed on the enemy, cutting through the air with the cold of strange depths. That ought to make an impression, he considered. To make it easier for Hailstorm to give them a chance to enter the crew. Sae’s words brought him back to reality. It took him a moment, but Goldenleaf noticed that the gruff voice did sound familiar. His mind went towards the dwarf runaway first, then considered the gnome that escaped battle at Northport.

“Seems like that, Sae.” Emrys answered rising his arcane focus, centering energy in it. Maybe I should cast Armor of Agathys anew. But maybe there would no time to replenish the energy necessary to cast a spell before facing Bart. In the end he decided to prepare to shoot it at the first enemy to appear. That or whatever rope they tried to use in order to board.  “I think our dear old friend needs a warm welcome. Cannon fire ought to be enough.”

Notes:  Emrys spends his bonus action to make the Tentacle of the Deeps attack (20 to hit, 11 cold damage). Assuming the pirate is dead, Emrys then readies an Eldritch Blast (15 to hit, 5 force damage) on the first pirate to approach (if the pirate approach by hope, the shot would be on said rope). If the pirate survives the Tentacle then the Eldritch Blast goes on him. 10 Insight to identify the voice.

Emrys finishes off the pirate... and the pirates on the boats are still busy putting out fires.

Yevelda chucks another javelin, attempting to skewer one of her former crewmates (and keep her rage up)

Attack: 26 Damage: 8

William looks around, panting heavily.

Seeing no one else on the deck, he (unwisely) asks "So... is that it? Are they retreating"

No sooner have the words left his mouth than a massive explosion hits the deck! Someone on starboard-side ship just cast a fireball!

Emrys, Sayyida, and Harold are caught in the blast radius... please make a DC 15 Dex saving throw against 26 Fire damage (half damage on a success)

Harold's save: 14