
Adrien Cavell |

Init: 1d20 + 3 ⇒ (1) + 3 = 4
Once it's Adrien's turn:
Quite a flare for the dramatic. Hope she doesn't take a warhammer to the head for it. Cavell thinks, moving quickly and quietly towards the hammer-wielding dwarf, before drawing both sabres in sweeping arcs at the Dwarf's back.
Stealth: 1d20 + 5 ⇒ (14) + 5 = 19
Attack1: 1d20 + 5 ⇒ (9) + 5 = 141d20 + 5 ⇒ (5) + 5 = 10
Damage1: 1d8 + 3 ⇒ (7) + 3 = 10
Attack2: 1d20 + 5 ⇒ (15) + 5 = 201d20 + 5 ⇒ (2) + 5 = 7
Damage1: 1d8 + 3 ⇒ (4) + 3 = 7

Trissae Darkwhisper |

Init: 1d20 + 3 ⇒ (20) + 3 = 23
On Trissae's turn:
"Oh am I now?"
If faster than the dwarf:
Triss will use her action to pick up her lute and move onto the rocks at (Q18). While moving she'll recover her rapier as well.
I figured that picking up 2 items would require the action for the turn, broken up by the movement of course. If you feel differently let me know and I'll modify this action
If slower than the dwarf:
Triss will disengage the dwarf, picking up her lute in the effort, and climb on top of the rocks at (Q18).

GM Grey |

Trissae - 23
Ozz - 21
Guards - 20
Giant - 15
Monrak - 12
Caira - 11
Adrien - 4
Feng - 2
Moving quickly, Triss Picks up her loot and rapier and climbs onto the rocks. Putting her about 10 feet up, too high for someone to reach her on foot, but not from someone on horseback.
Ozz is next

Ozz the Bog Ghost |

Ozz jumps out of the bushes, battleaxe in hand and swing at the human rider with the element of surprise (if his stealth beat the guys passive perception). Ozz isn't a fan of humans and elves, so though he usually just knocks the guards out, he'll attack to kill with this blow.
Attack with advantage: 1d20 + 5 ⇒ (16) + 5 = 211d20 + 5 ⇒ (7) + 5 = 12
Attack without advantage: 1d20 + 5 ⇒ (17) + 5 = 22
Damage: 1d10 + 3 ⇒ (1) + 3 = 4

GM Grey |

Ozz attacks with advantage, scoring a shallow hit on the human guard, who lets out a yell of surprise and pain as the battleaxe slices into his leg.
The guards begin to respond. The human rider retaliates on Ozz and the front dwavern rider joins him.
The human hits Ozz with his spear, dealing 4 damage. The dwarf misses!
The dwarf near Trissae hears the shout of additional combatants and grins fiercely as he rides up to the rocks and takes a swing at Triss with his warhamer.
The dwarf hits Trissae for 2 points of damage
The rear guard tries to ride up to the fight to be helpful, but can't maneuver through the terrain to engage anyone.
Giant, followed shortly* by Caira Spring out of their distant hiding spot and begin to dash toward the fight
Monrak Closes toward the dwarf guard trying to get the drop on him, but the dwarf rider sees him coming preventing advantage. Even still, Monrak lands two quick blows, nearly dropping the dwarvern guard who slumps in his saddle, his horse nervously staying in position.
Then Adrien moves, trying to get behind the dwarvern rider attacking Trissae. The human rider, just barely noticing Adrien sneaking toward his compatriot has just enough time to let out an all-too-late "LOOK OUT!" before his blades bite into the rider, dropping him.
Did you attack to kill or knock him out? Whenever you down an enemy with a melee attack you can declare if you want to just knock them out.
Feng, her main target eliminated by Adrien, moves into some bushes to get a clearer shot at the rear horseman. Spotting him, magic shoots from her hand in a brilliant blast of darkness, however the blast goes wide and shoots past him and his mount, streaking black through the slanting light.
Back to the top!MAP UPDATED
*(heh)

Trissae Darkwhisper |

A quick thumbs up to Adrien to let him know she's got command of the battlefield again, Triss thinks quick to push the advantage.
"Mornak! Ilmater favors you always!" She rabbles on the Lute to provide him a bardic inspiration (2/3) uses left. bonus action
She then quickly turns her attention to the rear rider as he approaches.
She casts Viscous Mockery "You've failed your master fool!" her words ring out attempting to cut harsher than a sword.
Viscous Mockery: 1d4 ⇒ 4 Wisdom save, DC 13. Disadvantage on the next attack if successful
She does a slight flourish standing in place as she does so

Ozz the Bog Ghost |

Ozz takes another swing at the human, hoping to kill him
1d20 + 5 ⇒ (2) + 5 = 71d10 + 3 ⇒ (2) + 3 = 5
"Raaa!" he yells furiously as his axe misses entirely, the guard leaning back in his saddle just in time to dodge the blow.

GM Grey |

The guard regains his balance in his saddle and thrusts his spear at the snarling, half-orc Bogshark once more. Ozz parries the blow with so much anger that it chips a notch out of the haft and sends the attack far, FAR too wide.
The dwarvern rider turns his horse to engage Mornak with his hammer, but the nimble hobgoblin easily ducks the blow.
The guard in the rear, angered by Trissae's words, kicks his horse forward to thrust a reckless spear toward Adrien. Even with the wild attack, it just barely scores a blow through Adrien's guard, striking deeply. Adrien takes 7 piercing damage.
Giant and Caira continue dashing toward the fight, Caira looking for a better angle on the enemy for her magics.
Mornak positions himself to attack the human, to try and save his life from being hewed down by Ozz by knocking him out. Two swift blows later and the human slumps in his saddle, safe from Ozz's murderous spite. The dwarf need not have been as afraid of Ozz as the human should have been.
Next up is Adrien, there is a horseman in your face, Feng nearby you and Giant & Caira right by the rear carriage, closing in on the fight.

Adrien Cavell |

Knockout on the dwarf then.
Cavell cries out in pain as the spear tears a gash across his shoulder, blood quickly covering his arm. The carefree demeanor vanishes and his expression becomes determined.
Healing Surge: 1d10 + 1 ⇒ (6) + 1 = 7
He strikes out quickly at the rider with his rapier. KO
1d20 + 5 ⇒ (20) + 5 = 25
1d8 + 3 ⇒ (3) + 3 = 6
crit: 1d8 ⇒ 5

Adrien Cavell |

Adrien shouts above the melee, "Surrender! Surrender and no one else gets hurt. We're only here for the goods, not your lives. You can be on your way after that!"

GM Grey |

"Yes yes!" says one of the dwarvern riders with a thick accent. The others seem also to be accenting to the robbery.
The three carriages are sitting still, chests and crates tied to the top of them. Mornak holds the reigns of the front horses, keeping them from bolting and blocking the others behind it somewhat.
The carriages themselves seem quiet, no one has yet emerged from them.
Giant and Caira catch up entirely, standing near the doors of the rear carriage. "Well, we robbin' these louts or not? What kind of fancy clan is this, eh?" Giant says, and spits on the heraldry on the side of the carriage.
Feng nears Adrien. "Are you well?" she says, taking your arm and looking at it with some concern.
Caira shouts out from the rear "Remember, the stuff on top could be worth looking through, but chances are they keep their money and jewels inside! Look for some kind of small strongbox!"

Adrien Cavell |

Cavell's grim look of determination fades and a smile returns to his face. He turns to Feng and glances at his arm, it was still bleeding badly but it didn't seem to bother him.
"Should probably wrap it I suppose," he mumbles.

Adrien Cavell |

"Crack it open then, what am I, the new boss?" Adrien says, a bit annoyed. He takes the weapons away from the two guards he knocked out and searches them briefly before turning his attention back to the carriages. He picks the middle one and struts over, knocking on the door.
"Pardon me, may we come in and rob you sir or madam?"

Trissae Darkwhisper |

"Feng, Caira! tie up the guards. Ozz bring them over to the girls then help Giant and Mornak start with the goods on top. Adrie..... beat me to it."
she hops down and chases to catch up with Adrien. Trissae wasn't really a leader but she loved to yell orders.

Ozz the Bog Ghost |

"Hey! Get down here!" Ozz bellows at the driver of the front carriage, so Monrak won't have to deal with any shenanigans from him.
Ozz will pick up the unconscious human (roughly) and then march the disarmed guard and the driver toward Caira and Feng to be tied up. He'll then hop up onto the center carriage to begin checking out its bags while Monrak does the front and Giant the rear.

GM Grey |

The group mutters their assent and begins following through.
Mornak waits for Ozz to take the driver away, mutters peaceably to the horses and hops up onto the carriage with a shout of "Just stay in there, nice and safe noble sirs and missus. We'll be with you shortly. Don't do anything foolish now, Ilmater would prefer you safe from violence"
Giant shouts at the rider on top of his carriage "Yeah, just stay right there, and I'll leave yeh be!"
Adrien finishes going through the unconscious guards rather quickly as they don't seem to be carrying much beyond their basic equipment and a water skin. As he knocks on the door, before Ozz even has time to drop his lot off with Caira and Feng, the door rushes open with incredible force.
Adrien, the door rushes toward you. Give me either a strength (Stop the door with might of your own), or a dexterity saving throw (dodge the swinging door).
As this door is slammed opened, all of the doors swing open as well and chain wearing, spear carrying guards empty out of the carriages, four from the front and the rear. Giant is struck by his door for minimal damage, but is shoved out of the way as he is off balance from the blow.
There are some other actions I need to have taken care of as well that can't be resolved until Adrien's save is known. However, I'll take another round of rolling initiative now to get it out of the way, as you guys have been out of combat for just long enough to change the flow of battle.

GM Grey |

As Adrien dodges back from the swinging door, his trained grace putting distance between himself and the carriage for the door to miss him entirely, as well as allowing the door to open all the way, a bulky, armored figure emerges.
Before the figure can even entirely emerge from the carriage, you hear a muttered word from further back inside the carriage, along with the smell of rose.
Adrien, you feel a sense of overwhelming lethargy moments before everything goes black. You are now unconscious.
Along with Adrien, Feng and Caira also slump unconscious over the bodies they had been tying up. Trissae, protected from these magics by the perks of her race stands conscious, while Adrien bore the spell in her stead.
The person emerging looks like this: She looks to be human and in her early 30s. She is wearing black plate mail and wielding a greatsword in her gauntleted fist. She Looks at Trissae square in the face and says, "Surrender, dog!" as she readies an action to swing her massive blade toward the drow if she were to twitch a muscle.
Past her, Trissae can see two people still sitting within the middle carriage as another guard leaves by the opposite door and takes position. One out of sight, only their knees showing in the confined space. The other Looks like a noble of some sort, middle-aged man, wearing a breast plate and a smug grin below a smug mustache.
The two drivers still on the carriage, each into the tied up luggage and pull out crossbows, aiming them threateningly. Some of the other guards ready their spears, either to stab or to throw, specially at Ozz, Giant, and Mornak, if they were to make the wrong move.
Knight - 15
Guards - 11
Trissae - 9
Ozz - 9
Monrak - 8
Adrien - 6 (unconscious)
Giant - 3

Trissae Darkwhisper |

"Ozz! Lead them to safety!" Triss yells, instilling Ozz with renewed inspiration. bardic inspiration (1/3) bonus action
"Aa' i' kalina en' Eilistraee en vanwa amin."
Before attempting to disengaging the imposing foe swiftly and moving to (t15) and throwing her arms wide in hopes of shielding her friends from potential crossbow fire.
Oh hell, my partner in crime is out cold, I'm screwed. Also I know its a readied action, I'm taking the chance.

GM Grey |

"Ozz! Lead them t-" Was all Trissae was able to get out before the greatsword came swinging around. Her version of unconsciousness was much less comfortable.
When Adrien comes to, he finds himself Gagged and shackled (both hands and feet) inside of a bouncing carriage. Ozz and Trissae are sitting opposite him, facing his direction, and seem severely unconscious. Blood spatters mark their faces, and they are similarly shackled and gagged. And disarmed. Taking stock of himself, Aiden quickly finds himself searched and removed of everything put his clothes. No armor, no backpack, not even any shoes. Curtains block the windows of the bouncing carriage. He feels rather well rested.
Sounds of talking diffuses in from outside, muted under the sounds of horses and carriage.

Adrien Cavell |

Adrien clenches his jaw tightly, ashamed. He tries to keep the shackles quiet as he checks to see if they forgot to confiscate any hair pins or the like in the female Bogshark's hair, hopeful.
If that fails, he'll search the floor of the carriage, desperate, before finally trying to wake the others.

Adrien Cavell |

"Triss. Triss," Adrien's voice drifts through the dark haze. She sees Cavell's face, grim and serious. He pats her cheek once with a rough calloused hand that smells like campfire smoke, seeming relieved.
"Good. Keep your voice down. Do you have a hairpin or anything, hidden somewhere? We have to get out of here before they can take us to a city, understand? If we make it to a city we're hanged."

Trissae Darkwhisper |

Trissae's vision blurs as she looks forward in the dimly lit carriage hold, searching for the familiar voice. Her face scrunches up when the realization of pain washes over her.
"S...sorry.. I just have a leather band to pull my hair into a tail for this outfit."
She examines herself taking Adrien's words into account.
"Maybe we could undo a belt and use the pin?"

Adrien Cavell |

Cavell quickly undoes the clasp of his belt and checks if the pin fits in the shackles' keyhole before he bothers destroying a perfectly good belt.

Adrien Cavell |

Are there windows to see out of the carriage?
"Damned. Good thought Triss. Try to wake the others I'll...I'll try to think of something," he says, looking around the carriage room. At least I'm well rested, but how long was I out? He wonders.

GM Grey |

There are heavy curtains that block line of sight but appear to be movable by hand. So long as you find something proper to act as a file for your belt pin, itll be a long term dexterity(theives tools) check to file it down and into the proper shape. Ozz is the only other one in this carriage with you. The fate of the others are unknown.

Adrien Cavell |

"Not enough time..." Adrien mutters, looking out the window. He gives a shot at searching the carriage for something to file the pin, knowing that a dungeon will have less than nothing to work with.
Perception: 1d20 + 4 ⇒ (6) + 4 = 101d20 + 4 ⇒ (5) + 4 = 9
Frustrated, he looks out the window again, trying to judge how far they are from either Everlund or Yartar.

GM Grey |

Looking outside the window you see a couple of the guards walking along side the caravan, same on the other side of the carriage. The group seems to be moving at a quickened past. You think that there might be some parts of the manacles with enough of an edge to file your belt pin, but it would be at disadvantage.
As far as the terrain goes, watching it pass for a while you see a landmark which makes you think you have a few days until you reach Yartar at this rate.

Trissae Darkwhisper |

Whispering.. "Adrien, what if you used the edge of my shackles to shave down the pin a little?" She begins to look around as well to see if the area they are in has anything of use.
Perception: 1d20 + 1 ⇒ (8) + 1 = 9
Unlikely finding anything she looks up to Adrien.
"Let's set the belt on the floor and put a knee on it, then grind with the shackle, what do you think?"

Adrien Cavell |

Spotting the landmark, Adrien seems relieved.
"I was wrong, we're a few days off from Yartar."
He pries the pin out of his belt, tying the ends together instead, and nods to the drow, kneeling to file the pin on her shackles. "They'll either stop sometime along the way to camp, or they'll need to rotate the guards. Whichever it is, it would be the best time to try escape. We'll steal a couple of their horses if we can."
Adrien stops to look up at her seriously. "This is bad though, Triss. If it comes to it, just run. Even if only you escape it's better than none of us," he forces a fake smile then resumes filing, occasionally glancing nervously at the carriage door and window.

Trissae Darkwhisper |

She looks to Adrien concerned. "A Drow lost in these wilds alone is dead. We all make it, or none of us will."
Triss stops him a moment, putting her hand on his, and smiles at him.
"We'll get through this."
Then she goes back to trying to assist him in filing the pin down.
if you need a roll and I'm not here feel free to do one for me

GM Grey |

Adrien, give me that dex ( theives tools) DC 13 check to see how well you start shaping the pin. It will take time, and several successes to get the pin properly shaped.
A bit of time passes and the fun fully sets, making work difficult (make checks at a disadvantage if you cant properly see what you are doing). The wagons slow and then stop, and you can hear the sounds of a camp being set up around you. These changes are enough the rouse Ozz at this point, who awakens to find himself imprisoned.

Adrien Cavell |

He shakes his head, speaking quietly while he works "If we can't sneak off, our best shot would be scattering different directions and meeting back up at the base. Pick between that or being hanged."
When Trissae stops him, he looks up, eyes determined. His expression turns to embarrassment and he looks back down at his work on the pin.
He mutters, "Should be me reassuring you."
Thieves' Kit: 1d20 + 5 ⇒ (1) + 5 = 6
Cavell slips and cuts his finger, cursing as blood drips down his hand.
"Damn it. Keep it down Ozz, we're trying to get out of here," He whispers angrily, blaming the slip on half-orc distracting him.

Adrien Cavell |

Cavell quickly wipes the pin on his pants then pops it in his mouth without hesitation, moving it to his cheek with his tongue.
When the door opens, he makes a lackluster attempt at pushing his way out, hoping it will distract from any suspicions. He also hopes he doesn't get his nose broken for it.

GM Grey |

Adrien's worries were indeed well founded. As the door begins to open, he pushed against it and is immediately thrown back as the door slams closed against him. A second later it reopens and you see the form of the plate wearing woman silhouetted in the carriage doorway.
"Start with the man", a calm voice speaks from behind her.
She looks at Adrien and points. "You. Come on out. If you try something I'll have to race the spears to be the first to draw your blood", she growls, staring daggers into the carriage at the lot of you.

GM Grey |

The woman takes Adrien by the shoulder, guiding him out of the carriage and into the firelight of the camp set up. As the door closes once more, the rest is cut off from Ozz and Trissae except for a rattling of chains once more.
----------
As she guides you out, keeping a hand on one shoulder to keep some amount of control over you, you can see this area better. Firstly, a guard secures the door with chain and lock once more. The three wagons have been driven off of the road into a clearing large enough to contain them. The area is fairly clear of trees and obscuring hills, and a small creek babbles nearby which the horses, untethered from the carriages, are drinking from under guard by a few men.
Each of the three carriages are placed a couple dozen feat from each other, and each has a couple guards stationed near it. Two campfires have been set up where some of the men are in the process of resting and eating. Small, individual sized tents have been set up near the fires though none currently look to be occupied. The dwarvern heraldry has been removed from the carriages and the dwarves, leaving both plainer than before.
Around you is the guard locking the carriage and two others, each armed with a spear ready to thrust at you if need be. Besides them is the plate wearing woman (A half-elf, upon closer inspection), a nobleman with a receding hairline and an oiled and well groomed vandyke beard, and a pale, gaunt man with a white streak through his somewhat unkempt hair. Upon hearing a harsh coughing, you spy a man sitting near one of the fires with a bowl of food. He seems a strong military sort, though out of armor/uniform. He has several scars on his face, and is staring at you with a detached interest.
The woman guides you to the center most of the three carriages (This one has no chains on the door. A successful perception DC 10 check will tell you if the far carriage is chained). The woman waits for the noble and the man with the white streak to enter it before roughly guiding you inside to sit next to her on one bench, the two men opposite you. The doors shut after you have all seated.
Inside, the carriage is lit with a word by the man with the white streak with a brilliant magical glow emanating from a spot on the wall between the two of them, casting them into a partial silhouette. Even still, you can tell that the nobleman is smiling at you warmly. The inside is more comfortable than the one you were just sitting in, better padding and thicker curtains to keep the chill night out.
The nobleman gives a nod and the woman drives her fist into your stomach. Take 2 points of damage. It is clear to you that she was holding her blow, and is capable of much more power should she desire to use it.
"Well well well..." the nobleman begins, his smile not fading. "It pleases me greatly that this little venture has paid off. We were worried that our sources were too good to be true! I suppose first things first. I'll have your name." He says all of this almost congenially, as if he is genuinely enjoying the chance to speak with you.