Waterdeep: Dragon Heist Reflections as a Dungeon Master

This is written as a retrospective from the perspective of a Dungeon Master, and reflections as a player might vary. Contains spoilers for Waterdeep: Dragon Heist.

Waterdeep: Dragon Heist is a fantastic adventure, and was one of the most compelling I had seen from simply reading the synopses of various D&D adventures. Its modularity was something that intrigued me, and the more I read about it, the more I knew I wanted to run this adventure. So when I was asked to be the Dungeon Master for a brand new group of D&D players, I knew what adventure I wanted to use.

The Campaign

This adventure was the first introduction to Dungeons and Dragons for most of the players at the table. I had been playing for a while, and I invited another veteran player and Dungeon Master to join, but the rest of the group was five brand new players who had never played D&D before. I chose this adventure largely because I wanted to run it, but also because I knew I wanted something concise and contained for their first adventure. Having the adventure be 1st through 5th level and fully contained within the city of Waterdeep was excellent. Having too much freedom or open-ended prospects can be overwhelming for new players, especially those less experienced at the game. Likewise an expanded setting would have been daunting for me to prepare as the Dungeon Master, and having the constraints of the adventure be limited to the boundaries of the city, it gave me more freedom to invest in and expand the structures of Waterdeep.

As the first official adventure module I ran as a Dungeon Master, I could not have picked a better one. Prior to Waterdeep: Dragon Heist, I had run game sessions as a part of a collaborative home-brewed setting, as well as independent One-Shot adventures. For this introductory campaign, I wanted something in an established setting, rather than a home-brewed world. Having an established world meant I had mythology and history to reference and that I would be able to draw from the established lore of the world. Waterdeep: Dragon Heist fit that bill perfectly. The history and lore of the Forgotten Realms is rich and expansive, and allowed me to fit a story into a world with detail and depth. 

As I prepared to run the adventure, I knew I wanted to keep the integrity of the Forgotten Realms intact, but that there would be room for some adjustments. I read through Chapter 1: Welcome to the Realms in Sword Coast Adventurer’s Guide to get history and context for the greater setting, and then set to reading the adventure so I would know the progression of events. My first read of an adventure is very cursory, without a fine attention to detail, instead focusing on the key events, understanding the preparation, and looking for where potential deviations from the storyline could occur. That allows me to prepare for responding to those key events, as well as to not be caught off-guard when there is a jump from the narrative, and I am ready to provide avenues back to the main plot.

What I Followed in the Adventure

More than just the story arc of the Dragon Heist, there were a few parts of the adventure book that I made liberal use of as I ran this adventure. Some of these were intentional from the onset, but some came as the game progressed, and I saw where my players gravitated, what they became invested in.

The first thing you have to determine when running Waterdeep: Dragon Heist is who the villain is. I purposely chose the Cassalanters because they presented the party with complex villains that operated almost entirely behind a facade. They are also enemies that are very clearly committed to fulfilling an evil act, but one that presented the party with a potential choice that wasn’t so cleanly made. It was also through an extremely unlikely series of events that the party was able to read the actual contract between Lord and Lady Casslanater and Asmodeus, detailing the specifics of the deal they had struck. They were at the point in the story when they were positioned to deny the Cassalanters the gold and make sure the sacrifice of 99 innocent souls would not be carried out, but they came to realize that by doing so, they were condemning the souls of Terenzio and Elzerina, the young Cassalanter children, to eternal torment in the depths of the Nine Hells. When presented with those choices, there was no easy solution for the characters who had high ideals, or those who sought to be better than the others they had seen. There would be no easy choices, only that of the lesser evil. 

Due to the nature of the villains and their ultimate plan, I tracked the timeline of the adventure by the Harptos Calendar. The Cassalanters’ goal was tied to a ritual that was to be conducted on Founders Day, so I made sure there was plenty of time before then for the players to be successful, but not so much that there wasn’t a sense of urgency. As time progressed, I allowed the villains’ tactics to become more aggressive and desperate. Early on, they had the luxury of time and could remain removed while making use of their reach within various avenues of influence. As the risk of losing their children became more real, I allowed them to become more overt in how they sought their prize. 

The various factions in the Forgotten Realms all have different roles to play in Waterdeep: Dragon Heist.

Supplemental to the main adventure, I made full use of the Factions in Waterdeep. Each character in the party ended up aligning with a faction, though all but two of them took membership with different ones. Two members of the party joined the Grey Hands, one took the Urban Bounty Hunter background (from Sword Coast Adventurer’s Guide) and was working with the Zhentarim, one became a member of the Harpers, another joined the Order of the Gauntlet, and my veteran player joined as a drow member of Bregan D’aerthe. This made for some brilliant roleplay between the characters, especially as several factions are not on good terms with each other. It gave the group a wide spread of information and access to people and resources, but also brought increased risk of compromise, especially when conflicting interests were brought to light. The Factions section detailed in Chapter 2: Trollskull Alley allowed me to make good use of the additional encounters to fill out the setting. 

Even though I was running the adventure with the Cassalanters as the primary villains, I didn’t want to just allow the other villains to not have a role in the future of Waterdeep. The Xanathar Guild and Zhentarim gang war became an ever-changing backdrop to much of the campaign, despite neither ultimately retrieving the Stone of Golorr or discovering the Vault of Dragons. The chapters detailing each faction helped provide source material to help expand their roles, even if much of it never came to light in the game sessions. One really exciting part was adding layers to the Zhentarim for the player who had the Urban Bounty Hunter background, and was aligned with the Doom Raiders at the start of the adventure. It helped give a unique glimpse into the large and powerful organization that has their own complex dynamics, all of which helped lay threads for potential plot lines that the party might follow in their next adventure. 

Jarlaxle Baenre, the charismatic leader of the Bregan D’aerthe.

I did however make extensive use of Jarlaxle’s villain narrative arc to inform how I roleplayed his character, though as an NPC rather than just a villain. His chapter gave context for his goals, which then informed his objectives, tactics, and resources. All that allowed me to better utilize him as a character in how he manipulated events in his favor, how he used a member of the party to extend his own access and reach. From there, it grew to how he was able to distribute his forces to subtly aid the party, make use of their progress, and eventually guide and follow them to acquire the gold in the Vault of Dragons. In the end, Jarlaxle might have been the only person in this adventure that got everything he wanted. 

What I Added to the Adventure

A significant amount of content I added to Waterdeep: Dragon Heist was original, not drawn from other sourcebooks or sources of “canon” material regarding the Forgotten Realms. Primary amongst the original content was the use of characters. 

I adjusted several NPCs from their descriptions in the book, changing them to have different roles or significance. One was adjusting Willifort Crowelle, the Cassalanter’s chief butler and Victoro’s personal attendant, from his original form as a doppelganger disguised as an aged tiefling, instead inserting him as an assassin in a character’s backstory. His character was further adapted to be the physical manifestation of the Cassalanters’ contract with Asmodeus, drawing inspiration from the Infernal Contracts section in Baldur’s Gate: Descent into Avernus.

I added new recurring characters that could serve a role beyond just allies or rivals. These are characters sometimes connected to other key entities or NPCs, and are present to provide lore, history, context, or simply to be additional, interesting characters within the larger scope of the world. I also gave NPCs connected to factions more intention as prospective mentors and allies than the book gave them. One example was expanding Savra Belabranta’s character, allowing her position as the daughter of a noble, as well as her history and search for redemption to inform how she interacted with our young, idealistic character who sought to join the Order of the Gauntlet to distinguish himself. 

In the realm of the mundane, I added a variety of resources to Waterdeep, with the intent of the city becoming a home of sorts to the party following the conclusion of this adventure, as they would likely seek to travel beyond its borders. I added magic shops, enchanters, armorers, and master craftsmen. I even added a runecarver, drawing inspiration from the lore in Volo’s Guide to Monsters and the Rune Knight subclass introduced in Tasha’s Cauldron of Everything, adding new mechanics for the players to utilize.

As much original content as I added to this adventure, I added a wealth of information from other sources, looking to other adventures, sourcebooks, and novels set in the Forgotten Realms. Some came from a diverse cast of characters, allowing the insertion of lore and history not mentioned in Waterdeep: Dragon Heist. Our dragonborn character hailed from Tymanther, which allowed me to introduce the lore surrounding the Spellplague. The goliath member of the party likewise came from the far east, traveling from the mountains that bordered Thay, bringing the magocracy into the periphery for the players. Several members of the party were native to Waterdeep, so I was able to give them a more comprehensive history of the city. And of course, our sneaky drow escaped from Menzoberranzan and allied himself with Jarlaxle’s crew, allowing me to give him the lore and history of the City of Spiders, as well as a larger context for the Sword Coast.

I chose to run the campaign as almost entirely canon up to the point the adventure began, barring any cataclysmic or setting-altering events, allowing the adventure to run in a more or less stable Sword Coast in 1492. There were no floating fortresses of giants signalling turmoil in the Ordning, no immediate threat of Elturel and Baldur’s Gate being drawn into Avernus, and no Death Curse spawned from the jungle of Chult, though some details from each of those respective adventures had some impact on the adventure and setting I ran. 

From resources like sourcebooks, wikis, and the novels, I was able to adapt NPCs and backstories from different expanded sources. That was particularly helpful in filling out the numbers of certain factions, particularly those that the party aligned with and had ongoing interactions with, such as the Harpers and Bregan D’aerthe. It also allowed me to have more context for Jarlaxle’s impact on the Forgotten Realms, once I realized he was going to be a powerful recurring character. His history was informed from the novels which detailed his adventures prior to his current task of legitimizing Luskan and gaining entry to the Lords’ Alliance. 

Other sources allowed me to open some limited mechanics from subsequent lorebooks that would have otherwise been inaccessible to the players with a canon setting. The opportunities from the expanded settings with the introduction of the dream of the blue veil spell in Tasha’s Guide to Everything, as well as other races, classes, and subclasses that would otherwise never be seen in the Forgotten Realms.

What I Would Have Done Differently

The biggest misstep I took while running this adventure was in how I approached the Downtime portion, when the adventure transitions from the introductory encounters to when the hunt for the Stone of Golorr kicks off. Looking back, I tried to split down the middle of allowing downtime to progress in an effort to let the players get to know the city and also time for downtime activities. I realized too late that it was premature both for new players and for low-level characters. I instead should have focused on hooks, encounters, and NPCs to have the world be busy and interesting enough to interact with the players and give them the freedom to branch out to explore, but not make that the expectation.

Waterdeep at night.

My players were ready for more combat encounters, and even though they carry more consequences in Waterdeep than other settings, I could have done better at interspersing encounters that were combat focused along with skill challenges to provide a variety of encounters to offset the purely roleplay situations. Many of the potential threads the players were able to pursue during Downtime (which is written into the adventure) often revolved around roleplay and creative narrative solutions. As the players at the table weren’t as experienced in following the leads to those types of hooks, those often felt unsatisfying, which falls to me as the Dungeon Master to better know my players and how they might respond to certain situations and challenges. 

Recognizing their unique style of play, and how it grew the more they played, certainly allowed me to better prepare how to run adventures for them, and how to present situations and challenges so that the threads might be followed, rather than ignored or missed. Learning the table and the adventure are a part of being a Dungeon Master, and it all comes with experience. 

Parting Thoughts

Overall, I could not have been happier with either my group or with Waterdeep: Dragon Heist as an adventure, especially as an introductory adventure. It made DMing really simple in terms of presenting the story, as well as providing inspiration and resources for introducing my own creative spin on the adventure. It made for a great opening sandbox for new players, particularly to showcase the complexities of a social setting with problems that cannot always be resolved through combat. It allowed my players to experiment with their characters in a relatively forgiving setting while they learned their characters and the rules of the world. I would highly recommend Waterdeep: Dragon Heist to both new and seasoned players and Dungeon Masters. From the exploration of the city of Waterdeep to the depths of the Vault of Dragons beneath it, this adventure kept me confident but on my toes as a Dungeon Master, and it was rare that I didn’t look forward to running a session of this adventure. 

Waterdeep: Dragon Heist is published by Wizards of the Coast.

Want to pick up a copy of Waterdeep: Dragon Heist for yourself or someone you know? Purchase a copy through this link, and you will help support the Writer in White with your purchase.


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