D&D Dragon Heist: Session 20

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Dragon Heist Session Twenty

Dragon Heist

Plot hooks a plenty

Little Joe hesitated. He had heard Alan give the order, but still wasn’t that familiar with human phrases. Take care of her? Did he mean really that? It seemed a bit extreme, but she was very agitated and in his twisted Drow mindset it did seem to be the humane thing to put her out of her misery. And Alan was the leader. Hesitation over, he moved forward and took out his dagger.

Last night was the 20th session in our online Waterdeep: Dragon Heist D&D campaign and after progressing to level three, our players had a lot to deal with in the aftermath of a botched faction mission.

The set up
We have been playing our Dragon Heist campaign via Discord and using Trello and D&D Beyond to keep track of characters and share campaign information. I have also been using a second laptop with its own Discord account so that I can stream battle maps for combat encounters. This week I even got to use some of my brand new dwarven forge terrain pieces. I was very excited.

dragon heist

To help with my Dragon Heist game prep and to flesh out the city of Waterdeep, I’ve been using supplements available from the DMsguild. So far, we’ve had an adventure with the Dungsweepers guild (Dung Work), interesting occurrences in the streets (Waterdeep: City Encounters), and a mission from J.B. Nevercott (Scrying into his Handkerchief). This week I used Waterdeep: Dragon Heist, Expanded Faction Missions to develop the session. This is a great supplement that covers the 18 faction missions included in the Dragon Heist campaign book, fleshing out the story for each, and giving them a bit more substance. I wasn’t sure which one to go with, so I prepared to set out story hooks for three missions and see which one they picked.

The party: 

dragon heist
The Party: Dugg, Alan, Arvene, Little Joe

Dugg, Earth Genasi Fighter – dungsweeper and estranged son from a noble family.
Alan Crabpopper, Human Ranger – a private investigator and member of the Harpers.
Arvene Galanodel, Half-Elf Cleric – priestess of Tymora, ex-city guard, ex-nun, fake harper.
Little Joe, Drow Sorcerer – channeling the spirit of John Wayne, secret member of Bregan D’earth.

Previously in Waterdeep

Alan, Dugg, Joe, and Arvene met in Waterdeep and formed a small independent private eye company called Dragonclaw Inc. Their first few jobs were dangerous and almost got them killed several times over. But they did have some success, including saving Renear Neverember, and investigating wererats in the Field Ward. They even managed to join a couple of factions that operate within the city.

Last session, during a mission from a mysterious haberdasher named J.B. Nevercott to deliver a stolen handkerchief to a deformed, homeless tiefling, the heroes suffered a catastrophic communications blunder. The tiefling girl, Advertence, became agitated and started screaming wildly in distress. Little Joe got the impression that Alan—the leader—wanted him to kill the girl, when actually Alan intended for him to cast a Sleep spell. So, when Alan told Joe to “take care of her,” and then walked away, Joe was only following orders…

Meanwhile, in Dugg’s world…

Dugg’s player was unable to play last week, so the genasi fighter wasn’t involved in the accident in the alley. He did, however, have a mini adventure via WhatsApp which took place in the space of time that last week’s session lasted (3 hours in-game).

As the party left the casino where they appropriated the handkerchief, Dugg turned to Alan and nodded to the backstreet behind the Gentle Mermaid as a female figure crept into the shadows. “That’s my cousin, I’m going to go catch up with her. I’ll meet you back at the manor.”

Esvele Rosznar

After a minute or so, Dugg found his cousin, Esvele, skulking in the alley. She seemed surprised to see him and quickly stashed something into her bag. A low perception check (8) from Dugg meant he didn’t see what it was.

“Whatever it was you guys were doing to Regnet in there, he deserves it,” she said. Esvele then spent a few minutes explaining how much she hated Regnet, and most of the noble houses for that matter, especially the Amcathras, Gralhunds, and Cassalanters. After a few more minutes catching up on family rumors she looked at her time-dial and seemed to abruptly remember a prior engagement. “Dang,” she said. “I’ve got to go. Only got a two-hour window. Gotta fly, cuz.”

With that she ran off down the alleyway, pulling a dark hood with a fine crimson trim over her head before disappearing into the shadows.

Confused, Dugg tried to follow, but couldn’t keep up. She evaded his attempts to track her and after another 15 minutes or so Dugg gave up and headed back to Trollskull Manor. He arrived well before his friends, and although he went straight to bed, he couldn’t sleep until her heard them all enter the building at 2AM. Once they were all back, he fell straight to sleep and dreamed about kittens and candy-floss and clouds that looked like famous architects.

“You work for me now”

Joe’s dreams were not so pleasant. He was plagued by visions of a heavily scarred and burnt woman calling out in pain. “Fire! No Fire! Help” Suddenly he was jolted awake. A blinding light was shining in his eyes. His feet and hands were bound to a cold metal chair. Disorientated, the floor seemed to shift and rock like it was rolling on water. A shadowy figure, features obscured by the blinding light stepped forward. Human. Male. Long hair, tied back. He leaned forward, just enough for his handlebar mustache and bad breath to brush against Joe’s face. “I know what you did Joe. You took the item. I need it.”

“Item? What item?” asked Joe, as the shadowy figure leant over and pulled an embroidered silk handkerchief from Little Joe’s pocket. “Oh. That item. You can have that. I didn’t want the thing to begin with.”

“Do your friends know what you did Joe? Did you tell them? What about Staget? What would the captain of the Watch say if he found out?”

Joe thought silently for a second. “I see… blackmail is it? Go on then, what do you want?”

The man stepped forward and into the light. A human, in his late 40s, naked except for two crossed red bandoleers and a red leather thong with knee high black boots. “I’m Zardoz. You work for me now. I own you. And when you get home tonight, nothing happened. Understand?”

“Sure. I don’t see how anyone would believe this encounter anyway…”

The man went on to explain that J.B. Nevercott would be along again with a new mission for Joe. He was not to mess this one up. He also introduced the two Drow gunslingers that would be following Joe around the city. Finally, he knocked Joe unconscious once more and when Joe woke, he was back in his bed in Trollskull Manor.


Once all the other party members were awake, they reconvened in the main tap room and discussed what their plans should be. Still unaware of Joe’s actions the night before, Alan wanted to stake out then alley way and wait for the mysterious man to collect the handkerchief from Advertence. Naturally, Joe tried to dissuade him from this.

Joe was in the idle of explaining what else they could do when there was a knock at the door, the first of a long line of visitors that morning.

Fletch Peterson, the stout surveyor and foreman who was overseeing the renovations to Trollskull Manor, had come to check on the progress. He updated the gang that the works were progressing much better than predicted and that it should all be finished in two to three days—four days earlier than scheduled. He also mentioned that Mirt, their benevolent benefactor, they guy who was paying for the works, wanted to see them, “Something about a rodent and a dagger,” was all Fletch could pass on.

As Fletch left, he passed the mail man on the way up the path. The group had just gotten back to discussing their options when another knock came at the door. The mail man—double denim, short shorts, and red plastic satchel—stood at the door and handed over two letters, leaving his empty hand palm up in a hopeful gesture.

Joe, frustrated by the constant interruptions and still on edge from the night before, cast Sleep on the mail man. Joe doesn’t tip. They shut the door with him passed out on the doorstep.

Avi and Embric

Before they could open the letters, there was yet another knock at the door. Avi, an air genasi and friendly local blacksmith, handed over an invitation to a birthday party for Embric (his fire genasi partner). He also had a basket of muffins and pastries for the group. “They’re the practice run for Thursday. You’ll have to ignore the taste; I got a bit carried away with the cinnamon. By the way, there’s a sleeping mail man on your doorstep.”

With that, Avi left and so the party had to choose what to do next. First, they decided to deal with the sleeping postman. I had hoped they would warm to him and that he would become a recurring friendly NPC; instead they dumped him in an alley way and covered his slumbering body with empty wine bottles. They didn’t even find out his cool backstory or quirky name.

Two letters

Having dealt with Jedediah Catflap, they opened the two letters. The first was from Alma Moyes, a friendly old lady from the beginning of the campaign. Her cat was in trouble, locked in a dock ward bookshop with a monster, and she had no one else to turn to. This was actually a secret mission for the Harpers, but they wouldn’t find that out until later.

The second letter was a summons from Captain Staget of the City Watch. It simply read: “I need to see you now —Staget.” Knowing the details of the proceeding day, this spread fear among the party. They decided to kill two birds with one stone and call in at the book shop on the way to the watch house.

Books, Books, and More Bloody Books!

They did a bit of investigating, mainly Alan and Joe wandering around accosting street merchants, and rolling very good investigation (19) and intimidation (21) checks, and discovered the location of the bookshop. It was a three-story building on Sourn Street called Books, Books, and More Bloody Books and was owned by another elderly woman called Eldra Shornfist; she too is a member of the Harpers. When they got to the building, they wasted no time scoping out the location, trying to ascertain the nature of the monster inside. Instead they barged right in and came face to face with an angry gazer.

dragon heist gazer
Having fought a gazer at level one, by level three it should be no problem at all.


Combat began straight away. The room they were in was three stories high of bookshelves, with ladders on wheels that spun round the circumference of the room, allowing access to the highest books. With his affinity for the natural world and a perception roll of 22, Alan noticed Catrick Swayze, Alma’s beloved pet, cowering 65 feet up, hiding from the monster. Meanwhile, the gazer was at ground level and heading straight for the party.

They managed to deal with the mini beholder in just under three rounds. It didn’t get a good chance to utilize its eye rays before being squished against the wall and popping like a bag of slime. Not for this first time in our Dragon Heist campaign.

As Dugg tried to pick the bits of gazer from his eyebrows, Joe and Alan attempted to catch the frightened feline. Clearly unsettled by the monstrous attack, Catrick Swayze did not want to come quietly. Arvene watched on as the two heroes dashed from bookcase to bookcase desperately trying to coax the kitty with whatever scraps of food they had in their packs. Eventually, with the aid of a petrified mouse, they were successful. “This cat better be rich,” thought Alan. END


Some really interesting things happened in this Dragon Heist session, and there were more plot hooks than any of my players could keep track of. The encounter with the mail man quickly escalated into something far more than I had planned. He was just supposed to be a slightly comic vessel by which the story hooks were delivered. But naturally, my players pulled on the least likely thread and before long he was unconscious in an alley way, covered in empty wine bottles and soon to be the subject of an internal audit from the highly assiduous Waterdeep Post Office department of internal affairs.

What did we learn?

DM Tip: Try to let your players explore any new abilities or character options they get from leveling up as soon as they can. Or at least make sure they have the opportunity to do so. My players advanced to level three at the beginning of this session and, although it was mainly role play based, having a mini combat encounter at the end meant they could all try out their new toys. Alan the Ranger is now a Horde Breaker, so he gets extra attacks when fighting multiple enemies; Little Joe, sorcerer, now has meta magic and can cast a quickened spell; at level 3 the cleric, Arvene, gets new spells and more spell slots; and Dugg, the fighter, is now a champion and so scores a critical hit on rolls of 19 as well as 20.

Next week in our Dragon Heist campaign the party will make a trip to Captain Staget and try to convince him they know nothing of the disappearance of Advertence. Will they be successful? Given their previous form, it’s very unlikely.




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