D&D Diary – Waterdeep: Dragon Heist – Session 4

The Saviors, the players, and the DM get lost in the city of Waterdeep, but manage to find their way to the only game in town: The Yawning Portal.

Waterdeep Dragon Heist cover title
Sadly, you will not be heisting any real dragons in the adventure. A “dragon” is the local slang for a gold piece. “Aw, we’re just stealing money? Again?”

When last we left our heroes, they had finally made it to the gates of Waterdeep after the world’s worst road trip. At the gate, they stumbled on some poor sap who was trying to smuggle invisible Trolls into the city. Things went downhill from there and there was some chaos, a little mayhem, a couple of explosions, and in the end, three dead trolls. And eight dead guards, but whatever, they’re expendable.

City Gate end
Oh sure, nobody cares about the dead trolls. They have rights too! I’m forming the Society for Protection of Indigenous Trolls. S.P.I.T.

Now the party is free to go into the city… after they get through customs. I wanted to have a little bit of levity and comedy to balance out the last few sessions, which were more grim and serious.

I printed up a bunch of questionnaires. The questions start out normal and get more ridiculous as it goes on. I played an unimpressed customs guard who was rather prejudiced against halflings, since the guard was convinced that whatever Callan said was a lie. Jack (Callan’s player) thought this was awesome and really played up being disbelieved even though half his answers were literally lies.

I had each player play out the quiz in character. It was a great way to illicit some roleplay out of my little murder hobos. I was afraid that the joke would get old before I finished, but all the players loved it and had a good laugh.

You can add whatever favor or foreshadowing you want to your questionnaire.

The best part was when I asked the players repeatedly if they had any affiliation with Halaster Blackcloak. Finally, Andrew, as Regizar, asked who he was. Without missing a beat, the guard says, “I have no idea, just answer the question please.” As the DM, I know that he is the mad wizard responsible for Undermountain, the mega dungeon beneath the city. But this lowly guard/bureaucrat would have no idea. The players thought this was funny and yet they still have no idea who Halaster is. Will they find out? Maybe, who knows?

Andrew also played Droop, his disguised goblin-butler, and every answer was a varied inflection of the word, Droop, ala Groot. Then I made up ridiculous answers as if this no-name guard could speak Droop.

The players are taxed for every weapon and exotic animal, and yes, I counted Droop as a dangerous animal. This was also a subtle way of saying that only the wealthy can be armed. I’m considering having a class war break out during our stay here, and this would be one of the points of contention for the lower class.

Griffon Flight
Ah, Waterdeep. Bright opulence and smiles above, but just below the surface – greed, corruption, and Evil.

Now, after 30 minutes, the party is free to go into the city… except, where do they go? This is perhaps the biggest problem I have with the Dragon Heist module. It takes place in, arguably, the largest city of the Realms, but we never see any of it.

For the entire adventure, the city is reduced to just one city block, with a few scattered buildings and set pieces thrown in. The whole thing is presented like a hodgepodge dungeon crawl. The single Inn in town is connected to a warehouse, then to a Sewer Hideout, a random Alley, a noble villa, and so on.

Map DH2.1 Trollskull Alley DM web
1000’s of buildings in Waterdeep; we’ll just give you 6.

The module fails to capture the grandeur of the city, and the whole adventure seems small because of it. On top of that, four possible villains are presented, but the module is designed for you to pick only one as the main antagonist, which makes the adventure seems even smaller.

This is not entirely the module’s fault. It is impossible to properly present a city of this magnitude and include a full adventure as well. Supplemental material is required. There are two products that I use to help my run adventures in Waterdeep. Either of these will help turn the very city into a living breathing character, with goals and plot hooks, hidden mysteries and secrets, rich with an incredible backstory and plenty of detail.

Waterdeep Dragon Heist cover villains
I really love the Xanathar creeping up from behind ready to devour them all.

The first is Accessory FR1: Waterdeep and the North. If I were to buy just one supplement it would be this one. This booklet is packed to the gills with information all specific to The City of Splendors but could easily be transported to any homebrew world in need of a coastal city.

The book details over 280 unique locations, including taverns, stores, guildhalls, temples, noble houses, and government offices. There are dozens of NPCs with stats and descriptions. The book also does a good job of explaining the power struggle between the three main factions within the city; the nobility, the guild barons, and the ruling class, which consists of anonymous “Masked Lords” who come from all walks of life, and whose identities are kept secret to avoid corruption.

Waterdeep Accessories
These should be required reading for anyone running a Waterdeep campaign.

The second book, Volo’s Guide to Waterdeep, is a terrific read. It delves deeply into the lore and flavor of every inn, tavern, shop, and feast hall in Waterdeep. It also captures the flavor and vibe of the diverse districts that make up the city, from the quiet opulence of the noble Sea Ward to the noise and squalor of Dock Ward. Hundreds of NPCs are given full description, but the book is more about story and less about stats so it is great for any campaign in any era.

For more of my hints and tips of running a campaign in a large city, please look at my post, How to Run a Fantasy City.

Back to our heroes. They had a ton of minor side quests things to wrap up. But frankly, neither my players nor I really felt like playing them out. But some of these encounters were important to set up some allies and some enemies and as potential plot hooks.

I started out roleplaying an encounter in the Heroes’ Garden, where James’ character, Riandon, can meet his Emerald Enclave contact. The Heroes’ Garden is a much better environment for the Emerald Enclave than a groundkeeper of a minor villa as written in the book. Plus, I placed some major foreshadowing in the public statues around the park and I wanted my group to find it.

DnD Park
BTW, if you would like to visit a real Dungeons and Dragons Park, you can, at the Jeremy Rochman Memorial Park on East No Name Road in Carbondale, Illinois. It has wizard duels, enormous dragons, and a castle with real secret doors and hidden areas. Awesome!

But everybody’s energy levels were really down today. I wasn’t very engaging in my presentation and the kids weren’t paying attention. Ultimately, I asked my players if we could skip these bits for now and get right to the heart of the story. Everybody was fine with this. Never be afraid to alter the timeline of the events in your session if it improves the enjoyment at your table.

So basically, I just told the players all the mundane, trivial bits. They claimed the reward for the wyvern. Riandon left his menagerie of animals with the Emerald Enclave. Regizar had his leg healed and Callan was cured of his addiction to his “Lucky Coin”. Clarissa met his contact with the Order of the Gauntlet. They are staying at a random mid-quality Inn called Gondalim’s and that their NPC friend, Garrick, will take them on a tour of Waterdeep the next night, starting with the most exciting tavern in all of Faerun, The Yawning Portal.

So finally, after three and a half sessions, we get to the actual printed adventure and right away, I’m changing it. First off, I don’t like the way that the book just has the players pick a “new best friend” from a list. That is so lazy; and a cheap way to force “engagement” on to the players.

Yawning Portal NPCs
The contrived “Companions” in Icespire Peak are better than these forced “Friends”.

Plus, I have gripes with almost all of these characters. I plan on having the players run through the events of several novels, including Blackstaff Tower, which involves Meloon Wardragon, and Godcatcher, which includes Jalester Silvermane. I will have these NPCs meet the party during those stories, and gain friendships organically. I had already done doppelgangers impersonating the tavern staff, so I will probably scrap that entire side quest. Another NPC’s sole reason to exist is to get the player’s into Undermountain, which is never addressed in this adventure, so she is useless at this time. They are all varying degrees of bad.

My second issue is mostly my problem. The adventure is written for character levels 1-5, but my players are already 5th level.  I will have to severely modify the challenge rating of almost every monster in the book. Oh, and I hate the fact that you cannot engage any major character in combat which is highly unsatisfying, but we’ll get to that.

WDH session5
My favorite unofficial Yawning Portal picture. Sadly, I don’t know the artist. I love the way the dwarf looks like he’s just going to jump in.

Our heroes enter what seems like any other tavern, although it is larger than most and is very crowded. The barkeep is serving drinks at the bar, attractive serving girls are gliding from table to table. A gaggle of drunken halflings are dancing around a table. A dour group of dwarves is sitting in the corner, shaking their heads at the antics of the halflings. A sour half-orc sits alone staring into her untouched ale. A bard is playing near a group of rough men who are drinking too much.

I set up my battle map and placed over 30 minis all over it, at tables, in rooms, around the bar. I had names and stories for each one of them. Nothing huge; just where they came from and what brought them here. I asked my players what they wanted to do and who they wanted to talk to. They didn’t care about any of it they were only interested in the giant black pit in the center of the tavern

Yawning Portal prefight
30+ opportunities to roleplay. Zero opportunities taken.

A huge, gaping hole in the floor is surrounded by a waist-high wall, to keep the more inebriated from stumbling to their doom. The vast chasm is 40 feet wide and round like a well; a well that doesn’t lead to fresh water but rather to mortal danger. The perilous portal drops over 140’ into the inky void of Undermountain, the fabled dungeon of epic proportions known throughout the land and irresistible to those with an insatiable urge to test their mettle.

Yawning Portal map
Everyone likes a clean map.

Immediately, two of my players ask, “Can we go down there”, which is the obvious question that this adventure refuses to address at all.

“Of course, you can,” I reply. “I am fully prepared to take you down there whenever you are ready.” And I was; I bought the original Undermountain Box Set, knowing that we will inevitably end up down there.

FR Undermountain Set
 I bought this long before Dungeon of the Mad Mage was announced. It is still impressive.

That seemed to satisfy their curiosity for now and they sat a table.

Soon enough, the drunken thugs approach the sole Half-Orc, make their ridiculous scripted threats and start a fight. Our heroes choose to… do nothing and watch.

The problem with this non-event is that there are no stakes for players and no reason for them to inject themselves into it. If one of the characters had blindly chosen the Half-Orc as their “friend” then they would have been obligated to join in, but that’s about it.  If I had had an innocent by-stander get assaulted during this bar fight, then I think my players would have stopped it, but I did not think of it at the time.

After the fight, the brawlers are kicked out, and I had a little interlude that at least two players enjoyed. Three adventurers were waiting to pay for the descent into the yawning portal. There was something very familiar about them. There was a kenku, and a tortle, and a bullywug. Conveniently, their minis were the same that we use in my Icespire Peak campaign, which my two boys play in also. They were scared that I was trying to kill their other characters, but, I swear, it is just a coincidence. I would never kill my kids off for a cheap joke.

Icespire Party 3pk
I feel a Dad joke coming on.

A crow, a turtle, and a frog walk into a bar. They ask the bartender for some Wild Turkey. The barkeep says, “You can’t get that here.” They ask for some Grey Goose. “Nope, you can’t get that here.” They try one more time, “Fine. How about some Red Bull then?”  The bartender tells them again, “No. You can’t get that here either.” Exasperated, the three ask, “Do you serve anything here?” The barkeep replies, “Oh sure, we serve lots of things, but we don’t serve animals.”

But I digress. I have Garrick, their NPC friend/guide/sycophant, explain about Undermountain and how the Yawning Portal can get you there, but won’t necessarily get you back. I also mention that the rest of the tavern takes bets about the outcome of the adventurers and whether they will live or die.

I was surprised and unprepared when everyone wanted to place a bet. I should have realized that all groups (including mine) would be very interested in this gambling, and worked out a real list of bets and odds. But I didn’t so I just made some up and it played flat.

YP Icespire Group
There is also a dragonborn (in red) in the Icespire campaign, but he didn’t fit the joke. 

The expendable adventurers from another campaign went down into the hole. The barker called out updates, “They’ve made over 1 minute down there.” A few angry patrons rip up their tickets. “Past the five-minute mark and no screams yet.” More patrons rip up tickets.

Just before the ten-minute mark, a scream is heard far below. A few patrons let out a whoop of joy. A panicked voice cries out, “Send the bucket, quick!” The bucket slowly descends. “Faster! It’s coming!”

When the bucket reaches the bottom, one of the patrons asks, “How many made back?” Another replies, “I can’t see anything yet.” There’s a tug on the other end and the winch operators begin cranking the slow ascent to safety.

Suddenly, the rope pulls taunt and snaps, sending the now-untethered rope hurtling back up the chasm. A sadly desensitized whoop of joy is heard from those who bet on no survivors. However, the cheering quickly turns to screams as an enormous monstrous beast crawls out of the well, followed by another.

YP Mound Attack
I love this guy, but I’m getting a little sick of painting nothing but green monsters.

The monster is a giant, lumbering tangle of vines and roots and leaves. Over 9 feet tall and almost as wide, it barely maintains a humanoid shape. It seems to shuffle on two stump-like legs and it shoots out extending vines from two sinewy appendages. But its head is just another mound of vegetation with no mouth, nose, or eyes. This is a Shambling Mound.

Shambling MoundThe first mound immediately grabs one of the screaming patrons and pulls him toward its body. As the hapless victim is pulled closer to the beast, more and more vines envelop him until he is absorbed completely into the monster to be consumed.

Durnan the barkeep immediately draws a giant glowing blade and vaults over the bar to combat this latest invader to his tavern. He yells at the players, “You four just gonna sit there? Take care of the other one.”

The combat as written includes a troll for Durnan and four stirges for the party, too weak for my players. But the Shambling Mounds proved to be a good challenge. The combat was a pure hack and slash, but a really good moment occurred when Clarissa was caught and absorbed into the monster. She had to spend the next few rounds clawing her way out of the beast. Later, Callan was almost knocked into the well. He had to make a dexterity save to grab the dangling end of the severed rope to save himself from plummeting 140’ to his doom.

YP Mound Swallow
I also love the way the dwarf mini fits right inside. And you can just see Volo and a mystery guest to the side, watching.

Eventually the party was victorious just as Durnan delivered the killing blow to his beast. “You fought well; almost as good as me. I thank you, kindly. Someday, you might even give that old pit,” pointing to the portal, “a real run for its money.”

A congenial man of indeterminate age approaches the group. He is wearing a poufy white shirt, tan britches, and a floppy hat. He introduces himself as Volothamp Geddarm, “But you can call me Volo.”

WDH session4
Well met. Sit down and let me buy you an ale. Say, you wouldn’t happen to have few gold on you to ‘ah’ cover expenses, do you?

Introductions are made and the adventure proper finally begins. Next week.

I’ve created a Waterdeep Dragon Heist Resources Page to compile all of the maps, handouts, and extras used during the adventure including all of my homebrew side quests. Hopefully, you will find them useful for your campaign.

As always, the Yawning Portal plays no favorites, she will serve and sacrifice anyone willing, and Game On!

Half of whatever Volo says is half true; the other half is half lies. – Elminster, mage extraordinaire and Volo fact-checker.

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