Waterdeep: Dragon Heist

Running Waterdeep: Dragon Heist – 5 things you should know about W:DH

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Running Waterdeep: Dragon Heist?

In this post, I will present 5 general tips for DMs who want to run the 5E adventure Waterdeep: Dragon Heist.

I ran Waterdeep: Dragon Heist right when it came out, so it’s been a while by now, but I have to say that it is one of my fondest memories playing fifth edition D&D.

Even so, Waterdeep: Dragon Heist is by no means a perfect adventure (you can read my review of Waterdeep: Dragon Heist here), but I do think its one of the most interesting and flavorful adventures published for 5E Dungeons & Dragons.

The 5 tips I will present in this article are general advice specific to Waterdeep: Dragon Heist, meaning that they are the ‘bigger things’ I suggest you keep in mind and prepare for, when running Waterdeep: Dragon Heist.

For more detailed troubleshooting and a chapter-by-chapter-guide to running Waterdeep: Dragon Heist (+maps, extra missions and more!) you can check out our DM’s resources for Waterdeep: Dragon Heist at the DM’s Guild.

Running Waterdeep Dragon Heist
The Complete DM's Bundle for Waterdeep: Dragon Heist has maps, advice, handouts, cheatsheets, and other DM's resources for Waterdeep: Dragon Heist.

Anyway, enough tongue-wagging, let’s get on with it: here’s 5 tips for DMs running Waterdeep: Dragon Heist.

1. Prepare the Players

Waterdeep: Dragon Heist

With a name like ‘Waterdeep: Dragon Heist’, it’s not too surprising that the adventure takes place mostly within the confines of Waterdeep. In fact, if you run the adventure as written, there’s little reason for the characters to ever leave Waterdeep at all.

Running a heavily localized, urban adventure has some benefits, but also potential drawbacks, depending on you and your players’ preferences. Either way, it’s something you will want to prepare your players for. A player playing a mountain ranger or a Circle of the Land druid may not have as much fun or feel as useful in an adventure like Waterdeep: Dragon Heist, as a Thief rogue or College of Lore bard would. 

Thus, having a session 0 – whether that is just a quick discussion on Discord before setting off, or a full 4-hour-session of character creation – is always a good idea, and especially so when running Waterdeep: Dragon Heist.

You can let your players know that:

  • Waterdeep: Dragon Heist is an urban adventure – you will spend most of your time in a city, in narrow streets, and small rooms. You may want to make characters that are useful under these circumstances.
  • Waterdeep has laws and rules that are enforced strictly. Try to make characters that can function in such an environment without constantly causing issues for the party.
  • There will probably be more roleplaying than usual, and many situations will be solvable using stealth or diplomacy instead of brute force. You may want to make characters that can do more than just hitting stuff.
  • Waterdeep has a rich history – if you want to, we can work together to create characters with backgrounds that tie into the city and its lore.

In summary, the first tip is: let the players know that they should create characters that are fun to play as – and with! – in an urban setting.

2. Prepare Yourself

Waterdeep: Dragon Heist
Urban adventures can be more difficult – or, at the very least, different – than your average travel-across-the-land-to-stop-the-villain or crawl-to-the-bottom-of-the-dungeon adventures. An urban adventure will probably feature more roleplaying and interactions with NPCs than your average dungeon crawl, and many of these have the potential to become recurring NPCs. Likewise, there is also a big likelihood that the characters will do what adventurers are wont to do in big cities: visit inns and taverns, go shopping, and explore the city, often on a whim. This can make running an urban adventure a daunting task, especially for newer DMs. How do you keep track of all the NPCs and locations in a city as big as Waterdeep? What do you do, when a player suddenly wants to visit a jeweler or a tailor? There’s some help to find in the Waterdeep Enchiridion that comes with the book. However, I would advice you to only try to read through that chunk of words if it really interests you. Preparing for an adventure shouldn’t feel like studying up for an exam! Instead of trying to learn all there is to know about Waterdeep and its denizens, you can focus on the important stuff – and simply wing the rest. You can do this by:
  • Focus on preparing the NPCs and locations the characters are most likely to encounter in the next session and think just a few minutes about how you would describe each, including personality traits and voices for NPCs. For chapter 1, the most important NPCs would probably be Durnan, Volo, Renaer Neverember, and possibly Captain Hyustus Staget. As you go into the following chapters, do the same for other important NPCs that come up.
  • For everything else, including NPCs that you have to suddenly improvise for one reason or another, just keep a short list of 5-10 names ready, possibly including a short personality trait (‘nervous’) and unique appearance (‘has bone earrings’). In addition, make up some names – just ideas, really – for shops and taverns, like ‘The Belching Beholder’, ‘The Dancing Dragon’ and ‘Argon’s Awesome Accoutrements’. Having just a handful of ideas ready will give you something to work with when your players invariably go off on a tangent and force you to improvise. While somewhat outdated, Volo’s Guide to Waterdeep has a lot of quick descriptions of NPCs and locations you can be inspired by.
Finally, the most important advice I feel I can give in regards to running an urban location such as Waterdeep is this: Relax. You may feel like you need to stay true to the enchiridion and the established lore and canon of Waterdeep. But you don’t. Really. Waterdeep: Dragon Heist is YOUR adventure and Waterdeep is YOUR city. Don’t overwhelm yourself trying to remember every little fact about Waterdeep. This isn’t an exam, and no one is judging you by how much you know about the city. Go with the flow, draw inspiration from the information in the book as much as you want to, but never be afraid to improvise and give Waterdeep a unique identity in your game world. In summary, the second tip is: spend a little time preparing the most important NPCs and locations, keep short lists with names and keywords for easy improvisation – and don’t worry too much about it, Waterdeep is YOUR city.

3. Choosing a Villain

Waterdeep: Dragon Heist has a unique gimmick: the DM gets to choose which of four villains – the Xanathar, Manshoon, the Cassalanters, and Jarlaxle – they want to pit against their players.

As written, the campaign book would have you decide from the start which ‘season’ – and thus, villain – you want to use in the adventure. 

Now, if you have one villain firmly in mind, you can definitely do that. But, you shouldn’t be afraid to wait a little with the decision, instead allowing the story to develop and see which villain the characters would have most fun going up against. 

Jarlaxle Wateredeep: Dragon Heist

The characters will organically meet agents of, or at least hear about, the Xanathar, Manshoon, and the Cassalanters during Chapters 1, 2 and 3 (Jarlaxle doesn’t necessarily show up organically, but you can always have the dashing rogue make an appearance somewhere). Observe the characters as they do so, listen to them discuss what they hear and see, and try to figure out which villain would be most fun for your players to go up against. 

If you end up changing your mind and going with a different villain than the season you chose to begin with, changing your mind isn’t too big of an issue. The season can also easily be changed by just shifting some descriptions around during the encounter chains in Chapter 4.

You can even run several villains at once throughout, really underscoring how everyone in the city is scrambling to get the dragon’s cache. This is also something we discuss in more depth in our DM’s resources for Waterdeep: Dragon Heist.

In summary, the third tip is: don’t get hung up on deciding a villain before the campaign even begins – see how your players react to the villains and choose the one (or several) that you think will be most fun, when you get to Chapter 4.

4. Using Factions

Waterdeep: Dragon Heist

One of my favorite things about Waterdeep: Dragon Heist is its heavy use of factions. 

Where other adventures will mention factions like the Harpers or the Zhentarim in passing, or have the characters run into agents of one or another, Waterdeep: Dragon Heist only really comes to life when the characters’ are invested with one faction or another.

The factions’ various missions are what fills out Chapter 2, and many of these missions will get the characters acquainted with Waterdeep’s various NPCs, factions, locations, and so on. In this way, using factions is really the key to unlocking the city of Waterdeep: Dragon Heist and tying the characters’ to the city.

Which factions the characters end up joining is up to you (who decide which factions you want to present) and the players (who should have the final say!)I personally like the Zhentarim, Bregan D’aerthe, and the Gray Hands, both because they all tie in well to the story and the city, and because their faction missions are some of the better ones. 

You can help making the alliance to various factions go smoother by letting the players know before the campaign starts (during a session 0), that factions are going to feature heavily in the adventure, and that making a character that is already a member of a faction, or open to the idea of joining one, is a good way to get the character more involved in the story. 

As a note here, there’s a bit of confusion about the Zhentarim, which it is important to be aware of. The book isn’t to good at actually emphasizing this throughout, but the Zhentarim in Waterdeep is actually split into two factions. There’s the Doom Raider Zhentarim, a band of adventurers that used to run the Zhentarim in Waterdeep before Manshoon arrived in the city and the faction was split into two separate cells. These two splinter factions have competing goals and different methods, and shouldn’t be confused with one another.

To summarize, the fourth tip is: do your best to get the players involved with the various factions, as it will elevate your game and enhance the adventure.

5. Running Chapter 2: Trollskull Alley

Waterdeep: Dragon Heist

Waterdeep: Dragon Heist’s second chapter may seem, at surface level, like it isn’t that important. There’s a tavern to restore, and a few faction missions the characters can embark on, but there’s not really anything of relevance to the story here. So why even both?

Well, first off, you absolutely can skip Chapter 2. If you just want to run a quick(ish) adventure, you can start the characters at 2nd level, head directly from Chapter 1 to Chapter 3, and you will have a story and an adventure that can probably be played in somewhere between 5–10 sessions. 

I’d argue, however, that Chapter 2 is the most important – and potentially most entertaining! – chapter in Waterdeep: Dragon Heist. Getting to play tavernkeepers is something the majority of groups seem to enjoy, and as previously mentioned, the faction missions really help tie the characters to Waterdeep and the story. You can find a ton of awesome faction missions for Waterdeep: Dragon Heist on dmsguild.com

You should also be very aware that Chapte 2 can be exactly as short, or as long, as you want it to be. Here, it becomes very important to read the room. Try to take notice (or even ask your players outright): is everyone enjoying running downtime, going on faction missions, and the day-to-day hustle-and-bustle of Waterdeep, or do the players seem anxious to get on with the story and the plot?

If the players like Chapter 2, you can even extend the faction missions well into Chapters 3 & 4, interspersing the story points – the fireball, Gralhund Villa, the encounter chains, the Vault of the Dragon – with various missions and downtime.

How to run Chapter 2: Trollskull Alley – including full-fledged faction missions and advice on how to keep the pace interesting by bouncing between missions and downtime – is something we go into detail with in our DM’s resources for Waterdeep: Dragon Heist.

In any event, the fifth tip is: put some thought into Chapter 2: Trollskull Alley, as it has potential to be the biggest, most important, and most fun chapter in the book! 


Of course, there’s a ton of additional tips that could have been put in here, but in the spirit of writing articles and not novels, I have tried to keep this list down to 5 tips. I’ll finish with a bonus tip, however, that is always good to keep in mind, and no less so when running Waterdeep: Dragon Heist: take advantage of the many online resources.

Whether that’s our free Waterdeep: Dragon Heist maps, the maps, missions, advice, troubleshooting, and cheat sheets in our DM’s resources for Waterdeep: Dragon Heist, the complete remix of the adventure in The Alexandrian Remix, or online communities at Reddit and Facebook, just know that there’s a ton of stuff out there for DMs running Waterdeep: Dragon Heist. Take advantage of that!

That’s it for this one. I hope you have great fun running Waterdeep: Dragon Heist – and don’t trust that J.B. Nevercott, there’s something fishy about him…

J. A. Valeur


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