Jalt hides behind the cart as best as a 6'7 Dragonborn can and is waiting for any signal form Breena. They've been through situations like this before, although not to this extreme. Realizing that he has little room for error, he waits there until he can perhaps see an opening where he might be able to move closer to the camp unseen.

Soar, make a Perception check as you look for a place where you might be able to talk unobserved.

Jalt, you can see that there is likely no way for you to move safely towards the camp. Also, it is getting dark; your lack of darkvision is going to be a challenge, as any light source would undoubtedly attract notice from above.

Perception: 13

Soar, you do see a cave that people appear not to be using much; you might be able to speak freely there, but it's very hard to tell.  Otherwise, you do see groups of people moving through the camp talking, and mostly ignoring each other.  

People are lighting torches, but also making preparations for night and for sleep.

Could I ask Breena, Elspeth and Soar for a straight charisma check (roll a d20 and add your CHA modifier).  There's no immediate effect of this, so please do carry on with the action and don't wait for a response to this check.

Once knowing his movements are very limited, Jalt will try to look in his immediate area to try and discern if there is anything like a natural rock formation where he can hide close to the cart with direct line of sight of the cart and the camp.

Jalt, you are pretty much hidden where you are now, although it would be easy for anyone arriving at the camp to see you as well.  You could back up about sixty feet and there's another rock formation, a bit off the main trail where you saw most footprints, where you could hide and look up at the plateau.  But the camp itself, that's in a hollow (imagine a stack of books and a bowl on the top with the camp inside), and you can't really see much apart from the one watchtower.  Moreover, when night falls you probably won't see much of anything.

Soar charisma: 19

She quietly points to one of the caves as far away from others as she can find and kneels down, takes off her pack, and begins to rustle about in a side pouch, trying not to attract attention. As she does this, she'll point at something nonexistent in the pouch, indicating to Badger and Elspeth to play along. While she tries to be a boring cultist reorganizing her pack and not attract attention, she whispers to Badger and Elspeth as quietly as she can. 

"That managed not to be a disaster. How are you two? I worry about our friend, though he can take care of himself and for anyone to be where he is, it's probably best it's him. Unless you think there's a way to have a reunion? He's got a... reputation and would surprise a lot of people if you know what I mean. Anyhow, I feel awful that I messed up the plan, I thought I was needed but apparently not. Now we are where we are, what do we do? Remember the goal. We have location, we need headcount, plans, bosses, reasons, and the injured boy's friend. Should we take a walk around and see what we see? Maybe one or two of us at a time?"

She pulls out a handkerchief and ties it around her head, pulling her now-dirty hear back and making sure the dirt looks normal on her face, hoping that she attracts less attention than she did before. Soar is ready to walk around in the twilight if that's the plan, looking for the monk from the boy's description, and if she sees anyone she recognizes from the last two days, she'll nonchalantly look somewhere else and divert herself from their path. She doesn't want to stay long if she can help it, but she'll start to try to get a general troop count, notice any leaders, listen in on conversations that are happening loudly enough where she doesn't have to get close to people and be obvious. She'll hope to overhear names and plans, and stories from the mercs and the cultists about Greenest.

Jalt would move towards the other rock formation, just so that if anyone comes to the camp they don't see him. Especially since he most likely won't see them.

Jalt, you are far enough away that you can back up and take shelter behind the rocks safely without being seen.  There is no sign that anyone above has spotted you.  The oxen are placid and silent, thankfully, and the cart comes to rest in a small natural hollow that would provide a pleasant resting place if it weren't a stone's throw from a camp full of raiders who would happily murder you on sight if they knew you were there.

The last of the light fades as the sun sets, and though the moon is bright enough that you are not completely blinded, you can barely make out anything in the surrounding countryside.   You settle down to wait.

(Don't worry, there will be things for you to do while Breena, Elspeth and Soar are otherwise occupied.)

Soar, from what you can see already, the camp is large and you'll need to walk quite a long way to do a proper survey.

(We'll take it step by step, but I'll let Breena and Elspeth decide what they want to do first, as you may be splitting up or staying together, it's up to you.)

Charisma: 21

Following Soars lead, Badger moves into the cave and is about the same height as Soar kneeling. "Normally I'd say that I could slip away and find him, people really don't typically pay attention to me, but these people don't like gnomes. They're suspicious and if I do anything that attracts too much attention, I could blow it for all of us. I'd like to find a way to get a message to him, though. Maybe we can write something down and I can ask one of the squirrels or birds to take it to him. Not sure they'll listen, but I can try." 

As long as Soar's confident no one else is close enough to overhear them, she'll speak a bit more forthrightly like Breena is.

"Great idea if we can get animals to help do the things that might blow our cover, Breena. Let's write a note saying 'do you want to get out or do you need help inside here?' and see if we can find him and a bird could bring it to him?" Soar says in response, stretching and looking around for anyone paying attention to them. Does she have a sense of what the caves have been used for at all by looking at them from the inside now? "How good are the animals at counting and finding out plans? Think we might need to risk ourselves at that. Maybe you can stay more out of sight and see if you can get animals to help scout and bring messages, and Elspeth and I do one circuit of the camp to get a headcount, listen in on conversations for chatter about the raid and future plans, and look for this monk guy, and come back here, and we can decide if we want to leave to find Jalt again, or do something else?"

Charisma check: 12

Elspeth will follow Breena and Soar into the cave, positioning herself inside to make sure she can see the mouth of the cave.

"Yes, that's perfect, Breena. If all else fails, I can carry messages back and forth. Would there be any point directly talking to the people in the camp? Could be risky, but then, It might help us find exactly the information we need. Would it be worth splitting up to gather all the information we need? It's a pretty large camp, after all."

You gather in the mouth of the cave, which does not extend far back.  You get one or two curious stares from passers by - you have a short time for conversation and planning, but you get the sense this would not be a safe place to linger.

Soar turns to Elspeth. "Do you think you could try doing one of those mystical druidy things, and turn into an animal to scout and listen? Maybe one of the animals we've seen around here that doesn't look like it could be food for hungry soldiers? That could be a really useful thing. And I can go around and maybe talk to someone who looks promising..."

Elspeth nods to Soar. "Yes, that was what I was thinking, since then I would have the added advantage of slipping into places the average recruit wouldn't be able to, but I'm uncertain what animals would naturally exist in a camp such as this. Perhaps something small, like a rat, or- well, I'll have to think about it, See if there's any beasts to be found here. Of course, that'll leave you alone - are you sure you'll be fine? Otherwise let's get out of this cave. I'll find somewhere where no one will notice me, and then come back into the camp."

"Maybe a lizard or a spider of some kind? I haven't been paying attention but maybe Badger here has. You could even ride on my pack and then when we got to someplace interesting, you could  dart off and listen and watch for a bit and then come back. Ooo- read a story once where this was a part of the plot... we can ask questions and if you want to say 'yes' tap your leg once and if you want to say 'no,' tap twice. Maybe once you return from looking around, so we know what you're seeing when you can't talk," Soar is really trying to modulate her voice in her excitement. She's staying quiet but you can tell it's a real strain. She looks at Breena, and says, "no chance you could disguise yourself as a kobold could you? Ah, just pull the hood of your cloak up and growl at anyone who looks too close and it will be fine, I'll cover for you. Don't want to separate us more than we already are -- I feel terrible Jalt's stuck outside. So why don't we try this and see what we can, and then try to get out of here, back to Jalt? We should get moving before someone looks into this cave more. Just roam around, looking like we're supposed to be here and not to be trifled with, listen and count, and then get out. We can do this!"

Assuming the others are good to go, and Breena's written her note, and Elspeth's wildshaped, Soar's ready to go look around. She'll adopt the affect and body language of the people she's seen around the camp as they arrived. No rushing around furtively, just matching the same pace and display of the others around her. If she can grab a bundle or firewood or something that makes sense, she'll do that to give herself an alibi or obvious intention. She'll try to stay away from places where people seem to know each other well. Going through the kobold portion of the camp she'll be as friendly as she was to the ones they entered with, speaking back in draconic brief salutations referencing the queen and general compliments of dragonkin if needed. But the idea is to get to the rest of the camp to see the scope, count troop strength, and get to a place where a lot of people are paying attention to something more interesting and watch and listen from the back. If there's someone Soar doesn't recognize from the raid, and who seems bored or likely to talk, she'd try talking as one soldier does to another. If there's a place where they could stop mostly out of sight for Elspeth to dart off in beast form to get closer to a high-level conversation, that's even better. If they see Leosin they'll stop at a similar position and try to let Breena get her note to a nearby animal to deliver it. Soar's still got dirt all on her face and in her hair, and her robe's hood pulled up so it's not easy to see her head.

Does that match what you all had in mind? Just trying to move things forward a bit but feel free to alter that plan or just do what you like!

You move together as a group; Soar has her face dirtied, Breena her hood pulled up, Elspeth still in her regular form - let me know if any of that is wrong, and if Breena is writing a letter, let me know what's in it.

You head together out of the cave, and move towards the first group of tents nearby.  They are clearly occupied by kobolds, who regard you with impassive faces as you draw closer, though you have not yet entered the little cluster.  The tents are poorly maintained, made of scraps of leather and cloth, but they look like they've been here for a while.

Make a Perception check to estimate the number of kobolds, and look for any useful information for the governor.

If you want to approach and talk to them, there's a single kobold sitting on a barrel and eating something about thirty feet from you, and a group of four sitting behind one of the tents.  Or you could head further into their little encampment, looking for others to talk to.  None of the kobolds that you see are from the group you travelled with today.

(Would you prefer we each roll separately, for for one to take the lead and someone else can help them? Asking since I assume a lot of skill checks for the group. Also Elspeth might have wanted to wildshape before leaving the cave but up to Ducas of course. Did we learn the names of the kobolds we traveled with? And FYI Soar, per the end of my last post, has her hood pulled up too.)

You didn't learn the names of the kobolds you travelled with. 

Any of you can make Perception checks, or choose to help another - though please actually describe how you will help them in a way that makes sense in the context. That will be the default rule for skills checks in this section, unless I say otherwise because I think the context demands something different.

Yes, I am pausing so that Elspeth and Breena can confirm that they are on board with what is happening, and add anything else they want to contribute.

Jalt, the sun has set, and you find yourself along in the darkness of the night.

Make a Perception check with disadvantage.