As he starts to give chase, Theldrin takes a moment to scan the layout of the neighborhood streets, making a quick analysis based on what he's seen walking around Pedestal thus far.

Investigation: 18

Khessa, hearing the name 'Irennaste,' thinks: 'Just as I feared... Our 'beloved' matron must have resented our refusal to bow to her extortion. There's no point in chasing her lackey; I think we should try instead to steal or destroy the letter now, while we may still have time... Failing that we'll have to try to eliminate Elessarwa quickly. With the matron dead, the guild won't be paid—and I doubt they're people who work for free and out of goodwill. Unfortunately, Xanrym had to act quickly—and he did not act in the way that seemed logical to me!'

The blonde arcane warrior, anyway, believes the bard is not currently in danger—because the drow, who came to deliver a letter and not to fight, is likely alone. So, before giving chase, she takes a moment to pour an Oil Flask into the mailbox and Fire Bolt quickly ignite the oil—and any non-fireproof letters in the mailbox.

Immediately afterward, the tall adventuress is more than happy to leave the scene of the crime and joins the chase.

Skill Challenge: Is Athletics okay, to run fast enough to close the gap on the others and the drow, I hope?

Khessa's Athletics: 25

Skill Challenge

Xanrym shouted and made some noise so that The Company knew where he went and could follow him if they wanted.  But once he's confident that Coriana is in range to see and follow Irennaste, he tries to avoid making noise and to use his invisibility to his advantage, slipping past anyone in The Riddle who might interfere with the chase and, in the end, sneaking close enough to Irennaste to stop him.

Stealth: 13 (or 27 if stealth advantage from his Cloak of Elvenkind still applies while invisible)

Skill Challenge:

As everyone starts to chase after the hooded person, Syllen will follow and keep watch for anyone that might get in the party's way. Pointing out dangerous individuals and avoiding anyone that would slow down the pursuit. 

Perception Roll: 8

(OOC: sorry for forgetting but how did guidance work for skill challenges? If I remember right one time I can give someone a d4?)

As Xanrym yells, he sees Irennaste look back and intuits the drow making a split second decision to head further down Skull Avenue, right into The Riddle. This will be an easy Skill Challenge, with the party need 6 Successes before getting 3 Failures. With 3 Failures, Irennaste get's away. With 2 Failures, there'll be a tricky fight at the end of the chase. With 1 Failure, there'll be no fight, but Irennaste will get the chance to scream, alerting The Riddle to his capture. You can roll any skill you have proficiency in, but only once. Keep it to 1 skill roll per post so that everyone has a chance to participate.

Coriana is able to successfully warn the others, and you are all involved in the chase, whether you wanted to pursue or not. Theldrin helps by looking around the streets and confirming they're likely heading to The Riddle, you're all able to head down an alley and head them off a little bit. Khessa pushes herself into overdrive, pushing ahead of the group and catching up with Xanrym with her superior athletics. Seeing Khessa taking the lead, Xanrym is able to go invisible and start to move through the crowd undetected, giving himself the advantage of surprise. Syllen scans the small crowds that litter the streets of The Riddle, but is unable to discern their intentions, he lags behind the group slightly. 

That's 5 Successes and 1 Failure.

(And yes Syllen can add Guidance to one roll in the Skill Challenge.)

[[I count 4 successes and 1 failure, Avery/Aagie didn't post.]]

Coriana sees Irrenaste rounding a bend, and there is an alleyway choked with garbage piled against a fence. Gambling that this could be a shortcut, she pops into the alley and uses otherworldly leap to cast jump to effectively gain advantage on her Athletics check. [[Athletics: 20]]

[[If this is not cool, she uses lucky again for the same advantage.]]

Quote from Charwoman_Gene >>

[[I count 4 successes and 1 failure, Avery/Aagie didn't post.]]

(OOC: After everyone but @Aaggie had posted, I posted a 2nd time for Xanrym.  The DM's narration didn't specifically highlight Xanrym's initial History roll, but it's part of the success count.)

Coriana slams into Irennaste and pushes him into Khessa, acting as a sort of brick wall. Before she does so, Irennaste let's out a cry loud enough for many people in The Riddle to hear, "I am Irennaste of House Dusklorn, I am under attack by thes..." He doesn't finish the sentence, having been knocked out against Khessa. A number of faces look out at you all with the unconscious drow on the ground. Seemingly angry and confused humanoid faces look at you inquisitively.

What's the Company's next move?

Khessa shakes her head: "Drow who can't stand hard drugs shouldn't be using them! What was he thinking? Start setting things on fire... Run away from us like he didn't even know us... Come on, my friend," she turns to Xanrym, hoping she's given him a way to put his eloquence to good use. "Let's take him home, shall we? Judging by the way he's looking, he's gotten himself into enough trouble for today... At least" she sighs "he's still alive..."

[[ OOC: What I'd like to do is give Xanrym Advantage on his next social skill check. ]]

Avery will watch the crowd while assisting with securing the Drow, making sure they don't interfere. 

"Yeah, let's get him somewhere safe to sleep it off," says Coriana, taking her cues from Khessa, and picking up Irennaste, Weekend-at-Bernies-style. She tries to walk him someplace secluded nearby. [[Deception: (Lucky) 25]]

Quote from Painted_Beyond >>

[[ OOC: What I'd like to do is give Xanrym Advantage on his next social skill check. ]]

(OOC: If that counts as Help, maybe Coriana can use it instead of her Lucky feature.  Assuming the chase took less than 1 hour, Xanrym is still invisible, and he intended to stay that way until we're sure that we don't need to sneak into some Assassin's Guild outpost.  Note: he did not see Khessa's attempt to burn Irennaste's note in The Guild's mailbox.)

(OOC: @drumdigby - it's unclear to me how many onlookers there are for this scene and how far away they are.  They may affect how we handle the situation.)

Xanrym arrives on the scene just as Coriana sends Irennaste careening into Khessa.  He remains invisible and observes any onlookers to ensure that they're not attracting too much attention.  Perception: 13 (if that should be Insight, that would be 8)

If there are no strangers close enough to hear, Xanrym speaks softly, his voice coming from somewhere just behind Coriana as he puts a hand on her shoulder.  "I'm here.  Try to move him somewhere private before he comes to."

But if there are strangers nearby, Xanrym remains silent and tries to stay out of the way so that he remains undetected.

Finally, if Xanrym notices anyone taking particular interest in The Company and Irrenaste, he'll keep an eye on them.  If they move away (e.g., to get help), he follows them invisibly at a distance.  If they instead follow The Company, he stays close to the party but watches to see what the follower does. 

Concentration: Invisibility

[[I'll put the luck point back if drumdigby allows it. Technically, Khessa only offered help to Xanrym so the use of lucky covered the advantage, if the DM rules differently.]] 

I thought of Xanrym, but since Coriana came instead, I think she can take the Advantage.

Anyway  last word to DM!