"She must be a very dear friend to you, indeed, if you are risking your life and your freedom to find her. Even though you do know if she is still alive." Sekkar was patiently waiting for his turn to be freed from the shackles.

"We explored the citadel above together, fought together and saved each other.  Additionally she has powerful healing through her god.  She is worth saving."

Kaylyn replies.

"she's the only cleric we got. We'll survive longer with one than without," Kastix states

Zeno grunts in frustration at the lock.  “It’s not coming.  Here, someone help me with this.” He’ll turn to help the others out of their manacles.

Thieve’s Tools on Manacles: 26

Quote from GoodShepherd >>

DM: what can I do about more thieves tool checks here for the door?

You could roll again with 'help' from someone (you can choose who, depending on how you think they are 'helping', such as confidence-building, knowledge of the lock, etc) in which case you can roll with advantage. If that fails, well I'll have to think of something else... :) 

((I see a 26.  Hopefully that's enough to get the manacles open.))

“Sekkar, give me a hand. Just lift right there, and *grunt* push, *grunt* lift there...”

Thieves tools:  24

Quote from GoodShepherd >>

“Sekkar, give me a hand. Just lift right there, and *grunt* push, *grunt* lift there...”

Thieves tools:  24

(Woohoo!!!)

Upon sighting the black chests, Rhayna spirits lift slightly. She remembers that Sarith mentioned that the group's equipment might be in Lady Ilvara’s private chambers. She hopes that her fellow drow prisoner is not lying. She turns her head straight, and closes her eyes, in a meditative pose. “Dear Goddess, I hope that you are watching over me at this moment, for little Rhayna here is going to be attempting something very foolish.” Rhayna slowly gets up, dusts her clothing, then she looks at both the quaggoths, and exclaims. “Agurra!! Egun ederra ... Err... Gaua ez da?” (“Greetings!! Beautiful day... Err… Night isn't it?” in Undercommon). She then smiles brightly to the creatures at the door. (As good of a smile that a nerdy cleric with thick glasses can give.)

She slowly walks to the nearest pillow and picks it up. She pretends to be admiring the design, the fabric, and inspects it from all sides. But she is really walking towards the hole to the lower floor. Once she gets there, she lets go of the pillow right on top of the hole. “Ops!! Jainkosa maitea. Zein baldarra naizen...” (“Dear Goddess. How clumsy I am...”). She looks down at the pillow on the floor below, then at the quaggoths. “Ondo egongo naiz.” (“I shall be right right back.”) She gives the creature another bright smile. She start to slowly go down to the ladder.

@Wolfy911: roll a Deception check, contested against the quaggoths' Wisdom check: 11

@GoodShepherd: With Sekkars aid, Zeno picks the lock to the cage. And once he's got the measure of the lock on the manacles it's only a matter of time before he has them all open. Strangely, Shuushar has already slipped out of his manacles, so his don't need picking.

Rhayna Deception: 10

(UGHH!!!!!!)

Quote from Wolfy911 >>

Rhayna Deception: 10

 um... can I not assume from your original post, with Rhayna praying to Selune for help, that you were planning to cast the Guidance cantrip on yourself?

(Yes, I forgot to mention that she will be casting Guidance on herself from this point on. Sorry)

Sekkar cast a glance at Shuushar, but at the moment his slipperiness did not matter much. "Can one of you, mages, make it look as if someone still in the pen? Just to be on the safe side. And if you asre still set on saving your friend, the Priestess Tower is this way. Wait for the next beast screech and go. We might want to divide now and move by different ways. Then meet past the pool. Those, who make it."

So... in order to maintain some dramatic tension, I'm gonna try something here. We don't know at what point the drow will fight off the demons, or perhaps just accidently notice the prisoners escaping, and I'd like it to be somewhat random. So we're gonna go round-by-round here, with each character declaring their actions. Each round I will roll a d20, starting with a target value of 5 and with the target value increasing each round. So for the first round, if I roll 5 or less, you have been spotted. In round 2 you get spotted on 6 or less. I'll make my rolls at the end of each round. In addition, because of how close the 'shrine' tower is to the battle, anyone approaching the door will have to make a Stealth check against a DC of "10 + the current target number" (to avoid being seen by the nearby drow), as well as against the passive Perception of the quaggoth guards (if still present).

@Wolfy911: Perhaps it's the fact Rhayna is in the shrine of a demon goddess, but Selune's aid doesn't seem to be enough to overcome the suspicion of the quaggoth guards, and with a barked warning "Ez zara hara joaten", they approach Rhayna to prevent her from descending the rope ladder.

Round 1 starts...

Rhayna smirks. "Perfect, the brutes are no longer blocking the door." Rhayna casts Calm Emotions (on a point behind the quaggoths, so she won't be affected), and then she declares calmly to the quaggoths. "Mesedez, ez da indarkeriarik behar. Gu, presoak, ez gara zure etsaia." ("Please, there is no need for violence. We, the prisoners, are not your enemy.")

(She is trying to make the two quaggoths in the room indifferent to the prisoners. May Selune come through this time.)

(Calm Emotions. CHA save DC 14)

Kaylyn rubs her wrists as she steps out of the cage.  She immediately tells the others, "Get equipment from the center guard tower (#10), I'm going to help Rhayna."

She moves towards the shrine to free Rhayna. Pensive flies down and lands on her shoulder as she passes through the guard tower.

Stealth 15

Sekkar glanced north - so nicely quiet and abandoned! - then looked at the central tower - so dangerously on the open! - and finally south, where battle still continued. He clicked his tongue at the sight, but went to the centre of the fort.

Stealth :18  (favored terrain)

Kastix will stay behind a for a bit, trying cast Minor Illusion to creates several hunched over shadows in the cage before following Sekkar to the center tower. 

Stealth: 18

Swinging open the gate, Zeno start to head to the tower, then a quick flash of emotion crosses his face.  He gives a frustrated look to Sekkar and Kastix and hisses, "Bah. Studded armor, and all the daggers you can carry... a hand crossbow and bolts if you have time." He turns and slinks towards the tower and Rhaynar.

Stealth: 18