After about 8-10 sessions with a group of four players, we wrapped our Waterdeep: Dragon Heist campaign. For the purposes of providing DMs new to the campaign with some lessons learned as well as some new ideas, here is my lists of things that went well, things that need improvement, and my favorite player moments. I hope it gives you inspiration!

Overall, I think Waterdeep: Dragon Heist is an excellent book to have simply for the ideas it presents, but this starter adventure itself is only good if you significantly adjust it, requiring a veteran DM to run it.

What went well in my Waterdeep: Dragon Heist campaign

The maps, dungeons, business, and city information presented

Do you want to run Waterdeep: Dragon Heist? What if you want to run the city of Waterdeep? How about building your own city for a homebrew? Do you want some great high level dungeons to use in your homebrew? What if your players want to run a shop or tavern?

If you answered “yes” to any of the above, I recommend buying Waterdeep: Dragon Heist.

Despite having a hot and cold campaign (more on that later), the amount of resources and good ideas on offer is incredible.

The natural flow of faction intrigue

From the opening moments at the Yawning Portal to the final encounters with the big bad, Waterdeep: Dragon Heist oozes with faction intrigue and political decision-making.

I kept a list of the factions (including villain factions) and kept tabs on the clout that the players (and individual party members) had with each. This helps to guide where some of the challenges become more difficult and will help characters out of bad situations, depending on where their favor exists.

Adding character backstories to the campaign

I ran this campaign during the same window as a separate Curse of Strahd campaign. One of my biggest issues with running that campaign is that it used older characters with no real ties to the world.

I decided I would use this opportunity to do more with players on their backstories.

I can safely say, character backstories are everything. They make adventures and campaigns original and make it easier to provide motivation.

If you aren’t spending a good amount of time building characters and their motivations, goals, and flaws with your players, you need to be.

I didn’t miss the larger world adventure

This entire adventure takes place in one city. Given that this is a level 1-5 adventure, the city environment proved plenty for the group of adventurers.

The different zones and quests, locations, and NPCs are just as big and wide-reaching as adventures up and down the Sword Coast.

The Cassalanters

While all of the four villains are amazing, I am fortunate the season selected and backstories created led us to the Cassalanters for the primary villains.

The story of this family and the way that they can interact with the players early and often puts them near (if not surpassing) Strahd himself as one of the best villains in a D&D adventure.

The NPCs

This should not come as a surprise, considering the influence of writers like Matt Mercer to this campaign, but the NPCs from front to back are great.

The villains, shop owners, faction members, guild members, and even sentient magic items have great personalities. Your characters will undoubtedly find at least a few they love.

What needed improvement with my Waterdeep: Dragon Heist campaign

Mysteries are hard

While I liked the mystery in Chapter 3 overall, I learned from running it that running mysteries in D&D is very hard.

There is so much a player can do or intuit based on a clue. You will find yourself face-palming within your perfect DM poker face. But this is not your player’s fault. This is a fault of a (thankfully) very open roleplaying system.

If I could do it again, I would provide many more clues and people with whom to interact to get the point across. The book gives you a lot of material, and even that was not enough. I would provide 3-5 methods to find each clue, and then yet more methods to tie the clues together into the explanation.

The adventure is terrible if run as written

Our group had an absolute blast running Waterdeep: Dragon Heist. However, this fun came in spite of the campaign presented in the book.

I found myself removing entire chapters (you read that right) and rewriting major story beats and encounters to provide a hook and keep the adventure running forward properly.

Most of my “needs improvements” stem from this overarching comment, so I will unpack it below, along with what I did to improve it.

The entirety of Chapter 2 sucks

Chapter 2 starts with a really undercooked encounter at your new manor.

I recommend playing the manor like a dungeon with enemies throughout, ending with a spirit boss, instead of the quick encounter written in the book.

After this, most of the chapter consists of sending random faction contacts to the manor to assign random missions for experience and faction favor.

To solve this, I leaned into the factions the players were favoring and tried to meld the faction missions into the story somewhat. I also didn’t linger on many missions and instead sprinkled them in throughout the campaign, which the book recommends.

The entirety of Chapter 4 sucks

After a good Chapter 3, Chapter 4 returns to the weird randomness of Chapter 2. As written, you might have to chase a MacGuffin through a number of locations. If you stop the chase, the MacGuffin just finds its way to the lair of the villain. At that point, you need to infiltrate the lair and steal it.

Instead of all of this nonsense, I had a rooftop chase from a faction NOT related to the main villain. If the enemy made it through the chase, they would take it to their lair, in which case the group would need to “heist” it. This did not happen in our campaign, as they got the MacGuffin just at the end of the rooftop chase.

The keys to enter the Vault of Dragons are dumb and anticlimactic

So, as written, you have just gone to many locations chasing a MacGuffin. Now, for the next scene, you need to… find three more MacGuffins to get a door to open.

I actually did run this section, but I chose the three keys for the Vault of Dragons that would be easier to acquire.

If I had to do this again, I would remove this altogether and just open the dang door.

The “Seasons” system

The “Seasons” system is cool on paper.

Basically, there are four seasons and four villains. You or your players choose a season, and there is a villain and environmental hazard tied to that season for your run of the campaign.

Theoretically, this allows for replay-ability, but I would just play the campaign by ear with your players and select the villain(s) that match your players and their motivations.

My players chose Summer, which tied to the Cassalanters, but I was leaning towards picking them regardless, given the religious slant of a couple of the characters and some early conversations with them. The players organically sided with the Zhentarim and had an enemy in the Xanathar. I didn’t even include the drow, because three villain factions was enough.

There are no heists…?

One of the final quests in the campaign is delving into a dungeon to steal half a million “dragons” (gold pieces). The problem is, it really isn’t a heist like you imagine it is.

Problem is, that is the closest thing to a heist in a game called Waterdeep: Dragon Heist.

What I did was turned the Gralhund Villa and Cassalanter Villa into real heists, where I gave the players a map and lay of the land and let them plan it out. I think this worked really well to give them the heist they were looking for.

My favorite player moments in Waterdeep: Dragon Heist

• The party latching on to Yagra from the very first encounter and making her an integral part of the story through until the end.
• “Fartboy,” the first goblin in the first dungeon… If you have been a DM for any length of time, you already know what this is about.
• Our warlock solving a problem with a hag by kissing her and becoming her life partner.
• The party capturing the Stone of Golorr on the last turn of a rooftop chase
• Our very much “WANTED“ cleric getting killed and reincarnated into a different race, so that nobody in the city knew who he was anymore.
• The monk’s desire to be with the Black Viper, despite her showing no interest whatsoever.
• One of the Cassalanters getting away at the end and not being seen again, an organic result of the way the party rolled.
• The monk’s dark past and organic connections to other entities via the elder brains mind network.
• Anything involving the sewers underneath the city, but particularly our artificer giving a lavendar scented token to the members of the Dungsweepers guild, which was paid back in kind by information later.