How to Bridge the Gap from Dragon Heist to Dungeon of the Mad Mage

This article contains major spoilers for Waterdeep: Dragon Heist and minor spoilers for the beginning of Waterdeep: Dungeon of the Mad Mage.

It’s a beautiful day. The sun is shining, birds are singing, and the 500,000 gold pieces hidden in the Vault of Dragons have been returned to their rightful place. So, why would any right-minded group of adventurers leave this idyllic scene to explore a deadly megadungeon?

Your Dragon Heist game may have ended a little differently, of course. Maybe you teamed up with your villain and split the gold, and now you have Laeral Silverhand’s Lords’ Alliance thugs on your tail. Maybe you went rogue and secreted a slice of the gold away for yourselves, where none but your own party can find it. Or, perhaps you made a big show of claiming the gold and you are being comically hounded by friends, family, “distant family,” and other less savory characters. Did your characters really come out on top? Did they get the gold after all, or were they manipulated, chewed up, and spat out by the nice, lawful bureaucracy of Waterdeep?

Regardless of how you finished Waterdeep: Dragon Heist, there’s a new adventure looming on the horizon. Your freshly 5th-level characters are now prepared to delve into the most famous dungeon on Faerûn: Undermountain. Located beneath the city of Waterdeep, Undermountain has only one (known) entrance or exit: the Yawning Portal Inn. Your adventure in Dragon Heist began with a drink in the Yawning Portal. Now it seems that your adventure in Dungeon of the Mad Mage will begin there, as well.

These two adventures couldn’t be more different. Dragon Heist is a short-and-sweet investigation-focused urban adventure that punishes excessive violence. Mad Mage is a lengthy crawl through a 20+ floor dungeon where vicious monsters lurk around every corner… but don’t think that the lessons you learned in Dragon Heist are useless. Alliances, even tenuous ones, will be vital to your survival in Undermountain. Many of its levels contain multiple factions that you can ally with or play against one another. Just look at this preview posted by Senior D&D Director Nathan Stewart, in which renegade goblins oppose agents of the Xanathar Guild, and all are tense at the potential aggression of a wererat gang, the members of another adventuring party, and the lingering remnants of arcane experiments gone awry. The tools of investigation and diplomacy your party honed in Dragon Heist will be put to good use in Mad Mage… but now there’s nowhere to run if you screw up. You’re in the claustrophobic halls of Undermountain now, and Trollskull Manor is a long way away.

Why the Hell Would you Go into Undermountain?

Here’s the elephant in the room: Undermountain is a dangerous place. Few who enter ever emerge, and those who do—such as Durnan and Mirt—are some of the most powerful and tenacious warriors in the Realms. However, those adventurers who have escaped from the deadly gullet of the Yawning Portal have emerged as some of Faerûn’s wealthiest and storied characters. The allure of fame and fortune is powerful. Some adventurers, regardless of their happiness and social stability, might wish to try their luck.

Quest Hooks

First of all, Dungeon of the Mad Mage is replete with quest hooks that will entice a party into Undermountain. Perhaps over and over again, if the party “comes up for air” at the Yawning Portal after a successful delve every few levels or so. But you and I both know that a quest hook—no matter how well written—only works if it appeals to the characters' wants and needs. You’ll have to understand what your players and their characters want in order for them to enter Undermountain of their own accord. This isn’t railroading; it’s successfully understanding and appealing to the emotional and logical forces that drive both player and character. Here are a few “end states” for Dragon Heist that might inform your characters’ desires.  


So you didn’t get the gold. For whatever reason, all of the money slipped through your fingers. Perhaps a villain got it, or perhaps the Stone of Golorr fell beyond your reach and all that gold still remains within the secret Vault of Dragons. Or, even more embarrassingly, you got the gold and instantly burned through your cut. Bonus points if you squandered it on living the high life like a classic sword & sorcery hero.

It may make you feel foolish, but the rags to riches to rags again plot that dates back to Robert E. Howard or before is a tried-and-true fantasy adventure hook. You need money, and where’s the one place that you can use your adventuring skills to become wealthy beyond your wildest dreams?


If your characters receive a letter one morning from Obaya Uday, Chultan priest of Waukeen (goddess of wealth and trade), seeking adventurers to help her recover an artifact from Undermountain… what would they be swayed by? Why, nothing more or less than the promise of immense amounts of gold, both as a reward and as plunder!


The characters completed the main objective of Waterdeep: Dragon Heist—that is, get the gold—and are reasonably well off as far as money is concerned. Unfortunately, their success came at a cost. They may have made a terrible enemy of the Xanathar Guild, and now must infiltrate Skullport by means of Undermountain to get rid of the price on their heads. Or perhaps one character is in desperate need of a magical secret, and her research reveals that the tome she needs is secreted away within the sanctum of Halaster Blackcloak, lord of Undermountain. Only an adventurer powerful enough to plumb the deepest depths of Undermountain could retrieve such a tome.   

What hidden bit of backstory can you tug on to get your characters to brave the upper levels of Undermountain? If you can link a loose thread to an artifact, person, or location in Undermountain, then you’ll have your characters chowing down on your trail of breadcrumbs.

Wealthy and Glory-Seeking

So, your characters made out like bandits at the end of Dragon Heist. Somehow, they got all the gold, or at least most of it. They’re loaded. They never need to work another day in their lives. For many players, that’s a perfect way to retire a character. If they don’t want or need to adventure, then don’t force them to go on adventures. Roll up a new 5th level character and lets do a dungeon crawl with a new party!

If you really want to keep playing with your Dragon Heist party, however, you’ll have to ask this question: how do you tempt someone who has everything? Fabulous wealth does smooth out most people’s base needs. They don’t have to worry about food, shelter, or entertainment, but that doesn’t mean that they are content. What’s that last trailing desire?

More often than not, it’s fulfillment. A sense of purpose. For some, that means making a mark on the world. That could manifest as a selfish desire for glory and further self-aggrandizement. It could take shape as a selfless need to make the world a better place. Or it could be anything in the shades of gray between those two points. What in Undermountain could satisfy that need?

Talk About it Together

You may want to talk these points out with your players. This will give them a say in the shape of your campaign, and it could also relieve the stress of trying to guess what will make your party tick. If there are parts of Undermountain that particularly excite your players, consider creating custom sidequests that take them there, or drop secrets throughout the dungeon that plays on their excitement for certain monsters, locations, characters, or artifacts.

How will you bridge the gap between Dragon Heist and Dungeon of the Mad Mage?


James Haeck is the lead writer for D&D Beyond, the co-author of  Waterdeep: Dragon Heist and the Critical Role Tal'Dorei Campaign Setting, the DM of  Worlds Apartand a freelance writer for Wizards of the Coast, the D&D Adventurers League, and Kobold Press. He lives in Seattle, Washington with his partner Hannah and his corridor critters, Mei and Marzipan. You can usually find him wasting time on Twitter at @jamesjhaeck.


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