SoW: Message from Brindol

Den of the Destroyer begins with the PCs back in Overlook, having presumably cleared out the Karak Lode and returned to Bran Ironfell with the happy news. A messenger will soon arrive with an urgent missive, but the adventure makes it clear that there is no set time frame for when that messenger must arrive. The beginning of Den of the Destroyer therefore makes a perfect time for the party to settle down and do those things adventurers need to do but can't in the middle of life-and-death adventuring. No, I don't mean drinking. I mean enchanting and disenchanting items, mastering rituals, and sourcing items that they cannot make themselves. It's easy for a DM to forget to make time for those activities, so it's good for there to be a natural "pit stop" before the action kicks off again.

Once the PCs have taken care of business, they run into either Kalad (the paladin from Siege of Bordrin's Watch) or Reniss (the half-elf ranger from Shadowrift of Umbraforge), who tells them that a messenger has been asking around for them. 

I'm impressed that two NPCs are mentioned here. It adds a level of flexibility to the adventure path, and it allows some room to manoeuvre for DMs whose players couldn't (or didn't) save Kalad, or who didn't hit it off with Reniss. There's no explicit advice in the adventure about which NPC to use, and while that might be a missed opportunity to educate new DMs on the fine art of relationship-building, I don't really feel that the lack of advice is problematic.

Making contact with Alys the messenger is a complexity 5 skill challenge (12 successes before 3 failures). The skill challenge adopts the same format as previous challenges in the adventure path, but the layout has changed slightly to include headers for each of the skills. I like the change, as it calls each of the skills out more, making DMing the challenge easier.

In order to do this challenge justice, I really recommend that you familiarise yourself with the Outlook information from Siege of Bordrin's Watch. 12 successes is too many to deal with them entirely in the abstract, particularly once the PCs discover that Alys has been kidnapped and need to track down her kidnappers. You'll also need a handy collection of fantasy-appropriate names for merchants, urchins, snitches and a few disreputable taverns.

I've previously expressed my dislike for long skill challenges, so I won't repeat myself here. What I will say is that this challenge gives you the perfect opportunity to put all that setting information from Siege to good use. If your players can't picture Overlook as a living, breathing place by the end of this challenge then they never will.