
Uriah Lewis |

Uriah of course, will lead from the rear.

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Ok, I have Ceidith, then two melee types, then the two archer types, then the two spellcasters bringing up the rear.

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This room contains eight cells, five currently occupied by prisoners who start begging to be released as you enter. A door to the east is barred from this side, and there is also a door on the south wall. A stone chair is bolted to the floor in the room's center, and interrogation instruments hang from the walls.
"Please! Please release us!" the prisoners call out in desperation.

Uriah Lewis |

Well, this seems like something you should be doing. Uriah says to Ander while gesturing to the prisoners.
They of course are completely innocent of all charges! The evidence was false! The witnesses coerced! Uriah says

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Before you have a chance to get a response, you hear the click of the door to the West as it opens, and you hear someone saying, "You rats better keep yer traps shut! Makin' all that noise..."
There is the briefest of moments where the guard blinks, as if he cannot believe his eyes!
You guys have a surprise round.

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Adrian, no roll necessary, it does not seem that the gnome's daughter is in any of the cells.

Uriah Lewis |

Go get em! Uriah points at the bad guy!
Giving Bardic Inspiration to Ander! +1d6 to any d20 roll this turn!
How dare you lock away these decent folk! May you be swamped with unlawful arrest litigation! Casting Vicious Mockery take 1d4 ⇒ 4 damage and have Disadvantage on attacks unless a DC13 Wisdom save is made.

Senka/Itzal |

Itzal snaps off a shot at the guard (longbow: 1d20 + 4 ⇒ (20) + 4 = 241d8 + 2 ⇒ (5) + 2 = 7), then steps back, using her companions as soft cover while maintaining a (relatively) clear shot at the other entrance to the room. (If I'm reading the map correctly...which sometimes I'm not sure I am.)
crit damage: 1d8 ⇒ 5

Wrathmire |

Wrathmire fires a few quick shots at the guard, hoping to drop him before he alerts more.
Hand Xbow Attack 1: 1d20 + 7 ⇒ (10) + 7 = 17
Hand Xbow Damage 1: 1d6 + 3 ⇒ (4) + 3 = 7
Hand Xbow Attack 2: 1d20 + 7 ⇒ (12) + 7 = 19
Hand Xbow Damage 2: 1d6 + 3 ⇒ (5) + 3 = 8

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The guard grasps ineffectually at the arrow that suddenly appears in his throat, drops, then falls face first to the ground!
However, he had barely come through the door and it swings open with the man's fall, revealing a three more guards and a pair of mastiffs!
The mastiffs charge into action, while the two mastiffs charge into the room!
Presmir Maurmeril 1d20 + 1 ⇒ (15) + 1 = 16
Wrathmire 1d20 + 3 ⇒ (20) + 3 = 23
Sir Adrian Fullbright 1d20 ⇒ 14
Ander Meliamne 1d20 + 1 ⇒ (14) + 1 = 15
Uriah Lewis 1d20 + 2 ⇒ (19) + 2 = 21
Senka/Itzal 1d20 + 2 ⇒ (19) + 2 = 21
Bad guys 1d20 + 1 ⇒ (15) + 1 = 16
Wrathmire 23
Uriah 21
Itzal 21
Dogs 17
Bad Guys 16
Presmer 16
Ander 15
Sir Adrian 14
Ceidith 6
Wrathmire, Uriah, and Itzal may take an action before the dogs emerge from the room.

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Wrathmire, I will use those shots as your first round of attacks.
Wrathmire feathers one of the mastiffs with a pair of quarrels, dropping it dead!

Senka/Itzal |

Itzal steps up, shoots one of the dogs, and steps back behind her companions.
longbow: 1d20 + 4 ⇒ (15) + 4 = 191d8 + 2 ⇒ (5) + 2 = 7

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Ceidith, you may post your action, but it will not take place until the bad guys get a chance to act. Put in an alternate action, in case your target doesn't survive.

Uriah Lewis |

I posted some actions....use those.

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[/ooc]Sorry. Missed those! Who do you want to give inspiration to?[/ooc]
Taunting the dog, Uriah quips, "Bad dog!"
Uriah 21
Itzal 21
Dogs 17
Bad Guys 16
Presmer 16
Ander 15
Sir Adrian 14
Ceidith 6
1d20 + 1 ⇒ (7) + 1 = 8
1d20 + 3 ⇒ (14) + 3 = 17
1d20 + 3 ⇒ (6) + 3 = 9
1d20 + 3 ⇒ (8) + 3 = 11
The huge mastiff whimpers at Uriah's feet, refusing to get up, as the guards yell at it to attack!
The guards snatch up their shields and spears and run into the room!
They approach as a wall, and attack Ander and Wrathmire! Two spears are thrust at Wrathmire, who dodges one, but cannot avoid the second! Wrathmire takes 4 hp damage! The third guard jabs at Ander, but the warrior-merchant shrugs off the blow, his chainmail stopping the thrust!
Everyone can go!

Ceidith |

Ceidith runs toward the nearest guard, and slices him with his shortswords, once, twice.
attk roll 1: 1d20 + 5 ⇒ (8) + 5 = 13
Dmg if hit: 1d6 + 3 ⇒ (5) + 3 = 8
Attk roll 2: 1d20 + 5 ⇒ (15) + 5 = 20
Dmg if hit sneak attack: 1d6 + 1d6 ⇒ (4) + (2) = 6

Wrathmire |

Wrathmire unleashes a flurry of bolts.
Hand Xbow Attack 1: 1d20 + 7 ⇒ (4) + 7 = 11
Hand Xbow Damage 1: 1d6 + 3 ⇒ (2) + 3 = 5
Hand Xbow Attack 2: 1d20 + 7 ⇒ (5) + 7 = 12
Hand Xbow Damage 2: 1d6 + 3 ⇒ (3) + 3 = 6
Hand Xbow Attack 3: 1d20 + 7 ⇒ (5) + 7 = 12
Hand Xbow Damage 3: 1d6 + 3 ⇒ (3) + 3 = 6
Action Surge, avoiding AoOs, moving to get shots without cover

Senka/Itzal |

Itzal pops out of what little cover she has and shoots one of the guards before ducking back behind whichever companion offers the closest bit of soft cover.
longbow: 1d20 + 4 ⇒ (20) + 4 = 241d8 + 2 ⇒ (8) + 2 = 10

Ander Meliamne |

Ander drops his torch onto the ground, then retaliates against the corrupt guards.
Longsword: 1d20 + 5 ⇒ (19) + 5 = 24, Damage: 1d10 + 3 ⇒ (5) + 3 = 8
Action Surge:
Longsword: 1d20 + 5 ⇒ (16) + 5 = 21, Damage: 1d10 + 3 ⇒ (6) + 3 = 9

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Round 2, GWF
Sir Adrian again swings at one of the Mastiffs.
[dice=GS Att]1d20+5
[dice=GS Dam]2d6+3
You can kill the already cowed (effectively incapacitated) dog, or you can attack the guards that are in the room already. I am just letting you know that the dog is obviously not a threat.

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Presmer utters his comment and stays his hand.
Ander, with two quick slashes opens the guard on him from gut to nose.
As Ander's opponent falls to the floor, Ceidith moves in swinging at one of the two remaining guards! The guard blocks the first attack with his shield, but the sneaky rogue manages to slip his second blade into the guard's side. That guard has taken 6 hp damage.
Wrathmire sends a spray of crossbow bolts at one of the guards, but they thud ineffectually in his shield!
Itzal threads the needle again, catching Ceidith's opponent in the eye! The man falls back, dead on the ground.
The remaining guard, looking at his friends that were systematically slain in a matter of seconds, chooses life and runs out the door to the outside.
Presmer and Uriah may take their actions before the guard runs away, otherwise, no one is within range for an opportunity attack (only Wrathmire is close enough, but has no melee weapons in hand.)

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Thought so, but didn't want to decide for you. Using your second attack as the attack of opportunity, since technically you have not had the chance to take your second round action until after the guard runs.
Sir Adrian navigates the battle with the practiced ease of a falcon, and swings hard, but overcompensates and strikes the stone floor, missing the guard!
As the guard turns to run, the half-elven paladin swings again, but the guard swings his shield turning the greatsword aside!

Ceidith |

Ooh! Adrian! You never want to put to much strength into a blow! You might overcompensate!
A rogue feature allows me to dash on a bonus action on my turn. Is it ok if I use that bonus action now?

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You can only do it on your turn. You used your bonus action on your last turn for your second attack. The guard's action takes place on 16 and yours is on 6. You may, on your turn catch up to him, but the others will not be able to keep up, so you may face him alone.

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The guard freezes in place! It is a small matter for the others to disarm him and restrain him.
He is yours to question as you will...

Ander Meliamne |

Ander glares at the captured guard, holding his torch uncomfortably close to his face. "Are you even really a Black Fist? What exactly is going on with this operation?"

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Natty 20!
The guard, already inclined to be cowed after watching his fellow guards destroyed in a matter of seconds, one by the very man questioning him, breaks down.
After a moment or two of blubbering, the thug manages to pull himself together enough to answer your questions.
"D-don't kill me! We are! We are!" he looks at his dead and dying friends, "I am, I guess... I... I... can't say... they'll kill me."
From one of the cells behind, a faint, strained voice speaks, "Wow, it is very different not being on the receiving end of that..."

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Ander looks over his shoulder and sees the bandit that he let live a mere 4 days prior!
"If you're looking for the gnome, they took her in there," the man gestures toward barred door, "But you'd best hurry, toss us the keys and I will get the others out. There is a beast in there. I don't know what, but those that are put in there do not come out alive..."

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The guard cries out, "No! She is still alive! We were trying to get information from her! But that Welcomer is right, we have a monster in there... The gnome girl hasn't broken yet, but we hoped that soon..."

Senka/Itzal |

Itzal takes up a position near the door (but not too close!), ready with her bow to shoot whatever hostiles might come through the door.

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Okay, I will need a rundown. Who is doing what? I have Wrathmire and Itzal. Is someone throwing the keys (which is easily found on the belt one of the dead guards) to the prisoners? Or conversely, are you questioning the prisoners first? Are there any further questions you wish to ask the guard?

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Most of the prisoners look starved and in no condition to fight, so that might not be the best solution. Even the guy that you recognize looks like he is in rough shape.
There are five prisoners in total. They look in rough condition, not likely to handle a fight, but can at least walk on their own. All except the fifth prisoner, who is curled up and rocking back and forth on his haunches. He seems to be talking to himself, but whatever he says seems to be nonsensical.
He also does not seem starved and dehydrated.
EDIT: Sorry, you said A cell, not one of other prisoner's. That would work. Though the three other prisoners still plead to be released.

Ander Meliamne |

Well, if the beast gets away from us and comes this way, they all might be better off in their cells until we can contain the situation. Seems to me that a post-beast-fight release is best for everyone, you know?