New to Sly Flourish? Start Here or subscribe to the newsletter.

This week Return of the Lazy Dungeon Master is on sale for 30% off the hardcover and 50% off the PDF and eBook package! Don't miss it!

Running Waterdeep Dragon Heist Chapter 2: Trollskull Alley

by Mike on 13 May 2019

Note, this article contains spoilers for Waterdeep Dragon Heist

This is one of a series of articles covering the hardback Dungeons & Dragons adventure Waterdeep Dragon Heist. You can read all of the articles here:

A Different Sort of Chapter in a Different Sort of Adventure

Waterdeep Dragon Heist is already a different sort of adventure than we're used to but, at least in chapter 1, it still feels like a typical adventure. A quest is given, the characters conduct an investigation, they crawl a dungeon, and face a boss. That's the outline of thousands of D&D adventures and it works really well.

Chapter 2 in Waterdeep Dragon Heist is nothing like this. Chapter 2 is mostly a toolkit for two major activities: restoring Trollskull Manor and getting connected with factions. There's no central storyline in this chapter and it's possible the activities in this chapter will take many tendays, months, or even longer depending on how you run it.

Running this chapter is not easy. If you find yourself having trouble running this chapter, hopefully this article will help.

Repairing the Manor

Much of this chapter will also revolve around repairing and funding the manor. It's up to you and your group to determine how much detail you want to expose in this venture. This event might be as simple as acquiring the funds to build up the inn once again. Maybe they hire an intermediary to do act as their agent in such matters, for a fee of course. Maybe your group really enjoys the detail of building out the inn. Some groups will love these details and some what to go off on adventures like they expect to. You'll have to gauge this yourself.

Choosing Factions and Quests

The rest of this chapter brings in seven factions that can potentially recruit the characters and send them off on a variety of missions. There are 28 such missions, none of which have anything to do with Raenar Neverember or the missing dragons.

I have two recommendations for these faction quests:

  1. Choose one to three factions you want to introduce and ignore the rest. You might choose the Zhentarim, Bregan D'aerthe, and the Gray Hands as three interesting ones to drop into the game. You might choose three others. You likely don't want to introduce all seven of these factions. Pick the ones that fit the characters and the game and dump the rest.

  2. Choose the faction missions which sound the most fun. There are tons of these faction missions and introducing them all can send the characters off on wild goose chases for weeks. Instead, pick a few that fit the current story of the characters and improvise any others you want to bring in.

Choose Your Own Adventures

This chapter is the perfect time to bring in your own small adventure seeds if you want. You can build these seeds from the backgrounds of your characters, inserting personal quests or group quests that focus on one particular character or another while they are busy fixing up the inn and dealing with the other issues going on. You can expand upon the rivalry between the new owners of Trollskull Manor and Emmek Frewn. Maybe it's your own little version of Patrick Swayze's Roadhouse. If you ever wanted to run some low level city adventures, this is a great time.

The Haunting of Trollskull Manor

For a more direct introduction to the chapter we can haunt Trollskull Manor, not just with Lief the poltergeist, but maybe with the hag mentioned in the manor's background. Back in Trollskull Manor's history, it was once owned by a hag who pretended to run it as an orphanage before she was routed by paladins of Helm.

What if that hag is still around?

This is our chance to add in some of our own mini-adventure. The two times I've run this chapter I added in a green hag named Auntie Potiti who had been routed from Trollskull Manor long ago but isn't fully gone. She still haunts the manor and adds all sorts of terrible discoveries including:

We can channel our best interpretations from It, Poltergeist, and The Shining to build out this our haunted manor. You might even replace it with your own version of Death House if you haven't run it before.

The hag might have a pet Banderhobb lurking in the cellar and the cellar itself might have a secret entrance into the Waterdeep sewers or even to Undermountain.

The goal of the party in this sequence is to survive the hauntings for one night and to route the hag. She will leave the manor but is still out there and may haunt the characters from time to time. Hags are fun.

The Mystery of Leif's Murder

Another interesting storyline to investigate in this chapter is Leif's murder. Perhaps the murderer was Leif's assistant, a young man at the time but old man now. Perhaps this assistant did so only after being fed lies by the rival innkeeper Emmek Frewn. Now the assistant is down at the dock wards, continually down on his luck. He has never forgiven himself for killing the only man who ever showed him kindness. It's up to the characters to find this killer and bring him to Leif, not so the ghost can kill the poor old man, but forgive him. In my game, one of the characters found out his name and used one of the paper bird messengers to summon him to the manor for a mysterious treasure. Smart!

Blue Alley

If your group needs more structure and you want to throw a dungeon in the middle of this chapter, consider running Blue Alley by MT Black. This deathtrap alleyway is a fun way for the characters to engage with some wild traps and earn some valuable treasure to help them fund the reconstruction of Trollskull Manor. The dungeon can be unforgiving in some places so add in some valuable relics so the characters can earn more coin or acquire one or two nice powerful single-use magic items for their adventures to come.


Whenever you feel like the pacing of this chapter is getting to be too slow, it's time to drop in the fireball. Chapter 3 of Waterdeep Dragon Heist focuses on the aftermath of an explosion that rocks the alley. It's a strong start to the rest of the story of this adventure. You can drop in this event at any point while running chapter 2 so it's a great way to help you tune the pacing of the adventure. If you ever feel like things are getting stale or boring, drop in the fireball.

An Open but Challenging Chapter

Chapter 2 of Waterdeep Dragon Heist gives DMs a lot of freedom to bring in new elements to the story. It also gives players a new style of game. Instead of chasing leads, fighting bad guys, and delving into dungeons; they get to build up their own home base, meet interesting factions, and go off on small quests. It's a way for them to feel the living and breathing city of Waterdeep.

This wide open narrative can be equally challenging to run. Take some time, shrink the aperture, and build it into the chapter you want it to be.

Related Articles

Subscribe to the Newsletter

Subscribe to the weekly Sly Flourish newsletter and receive a free adventure generator PDF!

More from Sly Flourish

Sly Flourish's Books

Share this article by copying this link:

Have a question or want to contact me? Check out Sly Flourish's Frequently Asked Questions.

This work is released under a Creative Commons Attribution-NonCommercial 4.0 International license. It allows reusers to distribute, remix, adapt, and build upon the material in any medium or format, for noncommercial purposes only by including the following statement in the new work:

This work includes material taken from by Michael E. Shea available under a Creative Commons Attribution-NonCommercial 4.0 International license.

This site uses affiliate links to Amazon and DriveThruRPG. Thanks for your support!