The blow leaves the half-elf reeling, her fingers wet with blood as she staggers in confusion, clearly not yet understanding what hit her.

Tam, roll initiative. The half-elf guard is surprised. If anyone else jumps in immediately,  roll initiative as well.

Half-elf initiative 8

[nat 20 total 21 for init]

Montar sees the half-reel and knows it is his chance. He quickly closes the gap and attacks with the found dagger. 

[Init 17]

Tam, take your turn.

[Nat 20! +3. Damage: I rolled a 1 on the d4 and 5 on the d6 (sneak damage) + 1 for Dex + crit (1 on the d4 and a 4 on the d6) = 12]

Tam quickly smacks the half elf in the head again, this time hearing a solid crunch as rocks crush bone. She winces at the sound.

The half-elf slumps unconscious and profusely bleeding to the side without even having the chance to yell for help. End of combat. 

Perception check for the other guard: 11

Nobody has noticed anything for now. 

Tam starts to drag the half elf into the bushes and quickly loots the body, looking for weapons and anything else of use. Hopefully Montar will help her.

Montar quickly shifts from readying to attack to helping hide and loot the body. "Nice work, lassie," he whispers. "Any chance you're as good at disguise as ye are at back alley work? I noticed that the special prisoner is also a half-elf. It may delay findin' out what we are about ta do if we can switch her fer him."

Also, Montar would be happy to switch the dagger he's holding for another, ideally bigger, weapon if the half-elfhas any. Seems like Tam could use the dagger.

(Meanwhile...)

Rather than argue or ignore the halfling, Amadeus follows. He sniffs the meat, feigning interest, and watches the process. Lightly guarded, excitable kobolds, a cart to escape on, potentially... he smiles, holding a bloody shank of leg in his hand. There're possibilities here. He eyes the commoners, subtly trying to discern their culpability in all this. Could they be swayed to assist or would they be an obstacle as well? Time will tell, he supposes. (What roll would you like here, DM, to gauge the commoners?) But first, I should press this one- his eyes drift from left to right, settling on the halfling in his peripherals -into potentially giving up some information.

"I... admittin," the gnome speaks wryly, putting on an air of illiteracy, "Oi heard me some word we was headin' out. Didn't hear where, though. Betwixt that fire early on and the last hit on that carriage, it's been a bli'er o' a few days. What 'bout you, love? Heard anyfing?" If nothing else, he figures, maybe she can let slip places to AVOID, so as our escape can be a clean one. 

Montar and Tam find a shortsword and a keyring with a few keys on the half-elf woman. Her clothes are rough, patched, and filthy. She's knocked out good and she won't be waking up soon if at all.

The dwarven woman eyes Thistlewick suspiciously as if he's the one she'd been asking about, then snorts and walks away without another word towards a small commotion nearby, leaving Draylin and the druid behind.

To the northwest, the halfling woman waits patiently as chunks of meat are tossed into wooden bowls. She slips away the moment she gets her share, narrowly avoiding being shoved aside by a half-orc. When Amadeus speaks to her, her expression brightens.
"Oh, of course! You're new here, aren't you?" she leans to whisper to the gnome. "I've been here 'couple of weeks now. There's lots of new folk that joined the last few days, you must be one of them if you still haven't heard."
"As it happens, you're in luck – I do know where we're headin'...." She adds with a hint of pride and pauses, letting the silence fill the space for an almost uncomfortably long beat. When she speaks again, her voice and face change slightly. "We'll be raiding Greenest tonight." 

For gauging the commoners (or anyone else for that matter, you can roll an Insight check)

Tam feels a sickness welling up in the pit of her stomach as she searches the filthy woman. She takes the keys and the sword

"Should we bind her or not worry about it?" Tam asks Montar. She hands him the short sword. "Can you use this?"

Then she looks to the two latrine diggers. "Psst, hey. Come here," she says from the bushes.

[not sure if the prisoners are shackled or anything. 

Montar eyes the sword with distaste. "It's shoddy, but aye." He hands Tam the dagger and exchanges it for the short sword. 

"I think we should do neither," he says, replying to her first question. "I think we should wrap her 'n a cloak, pretend she had a wee too much ta drink, and replace the special prisoner with her on our way out."

If the prisoners come over, Montar hands out some of the other cloaks he's been carrying to the prisoners. "Put these on," he says brusquely, but not unkindly.

“Do you want to carry her around?”

Montar shrugs. "Aye," he replies, and, after the half-elf is wrapped up, hoists her over his shoulder. "But I'll need ye ta do the talkin'."

The two young lads wince and turn to see Tam's head sticking out of the bushes. 
"Sorry, sorry, we are digging as fast as we can!!" the older-looking one cries out and begins to dig even faster. Their feet are bound by loose shackles too just like Ann's were earlier.

Tam swallows, unsure she’s up to the task. But a good reporter never gives up. 

“Okay.” Tam looks at the two prisoners. “We were captured just like you,” she begins. “We are escaping but since there are other prisoners we’re trying to get them free as well. Take these clothes as disguises and get ready to make a break for it when we give the signal. I don’t know what the signal is, but it will be something big. Be ready.” Tam looks at them to make sure they understand. She uses the keys to try to unlock their shackles but the f the keys don’t work she will pick the lock.

“Now, two other questions. We heard there is a special prisoner. A monk perhaps? Do you happen to know where he is being held? And two, do you know where the raiders keep the confiscated weapons?”

The keys unlock the shackles without any issues. The boys, who you now see are stinky, very young and covered in grime, shake their heads as they put on the clothes. "We know nothing 'bout a special prisoner. We just dig latrines. Where'd we go now to wait?"

The older one thinks for a moment. "I seen them get swords in a big tent back then." he points a dirty finger northwest, towards the camp entrance.

Montar turns to Tam, "Perhaps I missed somethin', lassie, but I was under the impression that the slumpin' figure we saw was the special prisoner. Do ye nae think so? That's why I'm holdin' this half-elf ta exchange. Why else would he not be being put ta work with the rest?"

To the two stinky boys, Montar says, "Make yer way toward the camp entrance. Look like ye belong."

(17+4, so 21, on that insight check, btw)

Amadeus' blood runs cold. Damn, seems things aren't so cut and dry. He may have to find his way back to the others sooner rather than later, relay the news. Drakes, whatever they are, a raid on Greenest, a way out (or perhaps back in, later), and the lapse in guards. What a shame, he laments. I'd hoped to investigate further. 

"Hmph!" He grunts aloud in feigned approval, keeping to the bit as best he can. "Fittin' ta be a good haul, then! Maybe they'd even give us some decent booze, not that rot they got by the fires. Should be a shoo'win, eh? 'Specially with them fellas in black. Joined up as soon as I seen 'em. Gives me da willies, but 'at jus tells me 'ere strong." Not exactly a lie there - they're definitely a nasty bunch. He exaggeratedly strokes his chin. "Y'know, my sword's not got much of n'edge on it. Ya think the boss'd mind if I grab'd somethin' from the pile we took offa dem last couple hauls? Bet I could get somethin' better ta cover what I nab!" He gives a chuckle, as if to suggest he's assured in his combat prowess. In reality, he could just barely swing his walking stick. Maybe I'll get lucky and it'll be at the top of the pile, he muses, pocketing a bony leg for his "take" of the meat.