As their little boat pulls in close to the ship on the far side, Ash will attempt to climb up, with her rope-and-grapple lashed over her shoulder like a sash.

DEX check for climbing (if needed): 9 

When she gets to the top she will a fix the grapple and lower a line down to help the others. All the time she is of course trying to be super stealthy.

Stealth check: 32 

Korrik, the guard responds "Ah. Right. Sorry. Nerves got me like... anyways, I'm Burns. And my comrade who went with the tiefling is Smithers. Yeah, sure. The tapping plan for steering sounds good." Burns is likely impressed as well by your shadowy shroud magic when you depart.

Ben, they use a combination of cargo nets, ropes, pulleys and various boards to shimmy the goods up and down into the boats from the ships and vise versa. None of these tools are out yet as they didn't know what exactly you were bringing. 

These ropes and things are not on the port side of the ship. However... with Ash's grapple and rope, there will be no need for the rolls anymore from Korrik and Ash. Any form of rope used basically removes the roll requirement. The grappling hook is a nice bonus. Nice one. Ash ties the rope once she's up, and Korrik will easily be able to climb up as well. Burns remains in the boat, port side of the ship. "Good luck." he looks scared. *No need for stealth rolls, the sea is quite loud here and no one is paying attention to the port side of the ship. Including the crows nest guy.

Ben, the guard who was talking responds: "Brandy and silk, brandy and silk... well what the fork else is new! Willard yeah? Hmmm... Bahahahaha! Fork yeah Willard, I was most definitely hoping it was Ruth again! Bahahahaha! Ok. Yeah yeah, sure, come on up. You too, Jay. Take a rest, we'll get the pulleys and ropes to haul the load up. The Captain? Hell, he barely helps out with the loading and offloading anymore. You know how many times we've done this? Plus he's a lazy fork. Ahem, don't tell him I said that though. Bahahaha! He's probably down in his quarters like the rest of 'em."

"Hey, Kur, you're not coming?"

Smithers would respond "Er, no I'm going to, um, take the boat back. I mean, I'll just wait here in the boat. I mean... uhhhh...." and Smithers just stares at Ben, waiting for him to get him out of this.

Ben, let me know what you will say to get this babbling buffoon out of this. Smithers does NOT want to board the ship. That was not part of the deal with them.

I will wait for that response, and then I will update the map and proceed with the next post which will include the guards getting the gear to unload the bigger stuff and Ash/Korrik getting up on the ship. 

"If it sells what's it matter! Nah, the boss is a lazy spork too. Mostly just sitting in his room doing 'magic'."

He leans over and looks at Smithers saying,

"Ya ain't taking that boat anywhere without me and Jay or with all that stuff."

Then to the others, semi-quiet,

"Kur's the nervous type, wets the rug like an scared pup. Got saddled with him cus he is scared of Grix, one of the hobbies. Just let him sit down there if he wants, long as he helps load, who cares?"

Persuasion(min 17): 16

He will actively not pay attention to the other side of the boat.

"Forking guy and his magic, I tell ya. Although, I suppose we should respect it. Shite's damn powerful. Maybe I'll learn it someday. Bahahahaha!"

(I was looking for anything higher than 17 here. That being said, your RP is solid and I feel there's no way the guy's not going to believe you at this point given what you've said and what you've referred to)

"Fork... who the hell are we recruiting these days?! Ahem... jeepers fork. Ok. Kur, it's ok guy. You just stay in the boat and lift the stuff up onto the pulleys and we'll pull it up." 

He looks at Ben and Ess and rolls his eyes. 

Ess would've stayed quiet for the most part, just basically answering questions if asked but really letting Billard do the talking. He is not nearly as awkward as Smithers is, and that is saying a lot for Ess. He's come a long way. He knows how to keep his cool. Or is at least getting better at it. He does say "Yeah. Me too, bro. I think I'll learn that magic stuff someday too, dude." 

Ok, the two smugglers plus Billard and Ess start to unload the fake goods. Smithers is lifting them up onto the nets and pulleys from the rowboat, and the others are either lifting it the rest of the way up, or using the pulley system and pulling it up that way. 

The guy in the middle of the map remember is 40 ft up in the crows nest. He can't see down on the deck, he's too high up, and also he likely won't hear anything as long as it's not super loud due to the wind and water sounds. He'd be scanning the horizon, making sure nothing is coming up on the ship as the unloading happens so isn't paying attention whatsoever to the ship deck. 

The smugglers, Ess, Billard and Smithers manage to get all of the fake goods onto the ship's deck. "Ok. Since you guys are new on the Ghost, let us lead the way. We've got a busy schedule tonight so there's no time for a bloody tour. Next time, ok? For now, let's just get down to the cargo hold, get this shite dropped and then you guys can be on your merry way back to the mansion. Looks like it'll take us a few trips. Kur can stay in the boat. *sigh*"

At the same time, Ash and Korrik are silently boarding the ship on the port side. They are unseen in this moment while the guys unload the boat. The crew are busy with the unloading, but once this is done and they were to turn around, they will see you. If Ben and Ess would glance over to that side of the ship, they'd see them. Once the loading is done, everyone will be proceeding to the door with the red arrow. That is the way down to the cargo hold. 

Korrik and Ash need to move from their location or they will be seen. Let me know what everyone is doing in this moment and roll accordingly (if Ben/Ess will follow/help the smugglers finish loading the goods down into the hold, and if Kay/Ash are hiding, with any bonuses to rolls applied. Ess will follow Ben's lead. Or perhaps something else entirely!?)

I've updated the maps with a new level of the ship as well.

Thanks!!

((I think Ash and Korrik are planning to climb quietly to the crows nest and kill the guy before he can make a sound, all while the cargo is being hoisted up and real smugglers are looking over the edge and/or pulling. I guess he’s not expecting that and we can sneak all the way up and pounce when his back is turned? Any rolls for getting up? Do we get surprise?))

*each of the smugglers would carry a cask I think, and they would be expecting Billard and Ess to carry one as well. Or a few bolts of silk.

Also... I forgot, Ess is wearing that hobgoblin's armor. I just remembered that now, and so I'm not going to do any retro for these smugglers on the deck noticing it, but it may come up especially if in an area that is more lit up and with a higher ranking officer. He might have to pass a roll... or Billard might have to bail him out. That'd need more than the 17. We'll see what happens!

((Thought he had the armor under something? Either way it shouldn't be a problem!

Ignore what else was written here, i somehow missed that huge block of text before Grwrobert's comment!))

"Ya, I want to crash before dawn anyhow. Come on Jay."

He scoops up some bolts of silk and follows, letting both of the real smugglers lead the way before finding Kay or Ash and nodding up to the crow's nest.

((yeah I think timing wise that would work - climb up and kill the crows nest guy as the goods are loaded onto the ship.))

((I forgot to mention, for the people who can't see in the dark, mostly the smugglers... there are lanterns fixed to the walls at each door which is providing help with the dim light setting. The inside of the ship likely will be lit.))

The crows next can be reached without a roll to climb or for the stealth. You will have surprise. Will both Ash and Kay climb up the rope ladder at the same time? One after another?

Crows nest is 40 feet above the main deck. Access to it is provided by a rope ladder whose lower end drops near the hatch on the main deck. The crow’s nest is an open, wooden platform, 10 feet square with 3-foot-high wooden walls. Opening a 2-foot-square hatch in the floor lets out the rope ladder that descends to the main deck.

The smuggler's gaze is towards the horizon, so is not paying attention if someone climbs up.

I am not sure about surprise. I say this because that hatch is currently closed. So, one of you will have to open it, climb through, and then do what you are going to do to this guy, all with him being completely surprised and missing first round of combat... seems unlikely. 

Here's what could happen - either Ash or Kay opens the hatch, and the other person climbs in and gets the attack. The smuggler is surprised, yes, but one of you will have to burn your entire first action in order to open that hatch. I think this makes the situation fair.

Do you agree?

If so, you can proceed with the attack roll however you're going to do it and whoever's going to do it. I won't roll any initiative yet in case the guy is killed before he can act.

*yeah there might be an overlap in messages - refresh always!

Kay can go first. Ash can make the climb in one go (60ft) with feline agility, so she can easily catch up.

Both get surprise and unseen?

Sorry lol just saw end of your post. I’ll have a think and wait for @spider too.

If the crows nest guy is looking the other way can we open the hatch a crack with +10 to stealth. And when he’s not looking we both sneak up with +10 to stealth. 

I feel like we could both get up without him knowing with our unnatural magical stealth. Plus we are both naturally stealthy (proficient) and practiced in stealth (background).

Maybe roll stealth to see if we both get surprise or just one?

Stealth: 20

Korrik heads up into the rigging, over to the mast and makes quick work of it, reaching the hatch and waiting for Ash. He contemplates the hatch.

((Does it open up, or down? If down, he has an idea...))

Ash’s Stealth: 36 

Ash follows close behind, wondering if they can silently: peek, open, pounce!

Ben, the other smuggler now says to the other one "Hey. They fixed the hatch to the cargo hold. Bloody thing just needed some oil. No need to go through the quarters anymore. Captain didn't tell ya?"

The other guys responds "No. He didn't. Jeepers and he knew we were getting a load tonight too. Dick. Ok, once we get the shite up on deck, let's just go down directly to the cargo hold."

He looks back at Ben and Ess "Yep definitely no tour tonight. Ok, it's down directly to the hold and then you guys can be off." 

So - the smugglers will now lead Ben and Ess down the hatch on the deck to the cargo hold once all goods are on deck. I've moved the red arrow on the map to show what I mean. Little audible there.

Ok, those stealth rolls would allow both of you to climb up the rope/ladder to the crows nest. The hatch opens downwards. Actually, the rope/ladder is attached to the hatch, and when the hatch is opened downwards, that is when the rope ladder is released down to the deck. I overlooked that piece. So, the crow's nest hatch was already open to have the ladder hanging down. Stealth rolls were still needed to climb the ladder and get close to the nest, which you did. However, you are only able to get 15 ft to the crow's nest without the guy noticing, regardless of your stealth roll. The roll got you to the 15 ft away mark.

What will happen next? Ash and Ess will have to be out of line of sight when the smugglers go towards that hatch on the deck, which they are if they both climb up the ladder.

As far as surprise, after thinking about this, yes the dude will be surprised for round 1. Remember you guys are one after another on a rope ladder and are 15 ft away from the opened hatch. 

The smugglers on the deck along with Ben, Ess and everyone else will not roll initiative unless this goes south and the crows nest guy manages to survive and yell out. 

In case it's needed: crow's nest smuggler initiative 15 (surprised rd. 1)

Ash and Korrik, please roll initiative if you plan on making a hostile move here, and then go ahead and let me know exactly what you plan on doing.

Map updated!

((Forgot to mention, but when the guard agreed to the approach and the boot tapping to steer, Korrik steepled his fingers and said "Excellent...".))

Korrik pauses on the rope ladder, glancing upwards, and the opening of the hatch fills in with a hazy shadow to further obstruct their approach. 

He climbs upward, popping through the illusion and laying into the crewman, making sure Ash has room to scurry up and join him.

Fist Attack: 16 Damage: 6

Elbow Attack: 18 Damage: 5

  Initiative: 12

((Ugh, don't know what happened, my initial rolls were good, I edited in the bit about Ash joining him, and then they got 'locked' as something different (neither initiative or attacks was above 11. yuck.). Moved the initiative to 'break' it, and I'll reroll and take whatever comes up below.))

Initiative: 8

Fist Attack: 16 Damage: 4

Elbow Attack: 17 Damage: 7

Ash’s initiative: 7 

Ash follows Korrik up and draws her daggers. She attacks twice, trying to finish this quickly...

Attack action: Attack: 13 Damage: 6 (piercing damage)

Bonus attack: Attack: 19 Damage: Unable to parse dice roll. (piercing damage)

If either attacks hit, add 6 sneak attack damage.

((OOC: boom!)) 

As Ben lugs the silks he asks,"You two got names? Gonna be odd if I start having to call you dude or something."

((Crit doubles the sneak too! Just don't try editing it in to roll, DDB is finicky today!))