D&D Waterdeep Dragon Heist: Session 16

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Waterdeep: Dragon HeistDragon Heist Session Sixteen: The Waterdhavian Job

Back in the tavern, the members of Dragonclaw Inc. discussed their plans for getting the magical sword back. They knew the tavern where it was being kept, and had a rough description of its owner, but little else. Arvene volunteered a plan, “If I go to the bar and ask for the man with a limp, say I’ve got a ‘rendevous’ with him, perhaps they’ll show me to his room. Then I just signal to you guys and away we go.” It was a terrible plan. But they agreed anyway. “Right, let’s go then.”

Last night was the 16th session in our online Waterdeep Dragon Heist D&D campaign and our heroes had planned a heist.

The set up

We have been playing 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.

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This week our Ranger/Investigator Alan returned after missing a session because of a miserable cat, so the party were finally reunited with their intrepid leader. I had been messaging him prior to this session to work out what Alan had been up to while away. As the others were sweeping up muck and planning a heist, Alan accepted an invitation to join the Harpers—a clandestine organization that promotes political fairness and equality through covert means. Would he share his new affiliation with his companions? Probably not.

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When he couldn’t make the session, I whatsapped Alan’s player and we worked out what Alan had been up to in the meantime

The party: 

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

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The Party: Dugg, Alan, Arvene, Little Joe

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.

At the same time, Dugg, being a very savvy earth genasi, had found a little side hustle to bring in some extra coin. He had joined the Dungsweepers Guild as a reserve sweeper. Last session our heroes were called upon to help out the sweepers and they spent the first of two days with the guild. They ended that day planning a heist to return a stolen sword to a tavern owner in the Trades Ward. Now they just had to pull it off.

If you take the High Road

As Arvene, Dugg, and Joe made their way toward the Dripping Dagger, Alan was traveling south along the High Road to the Trades Ward. Feeling pleased with himself, he pressed the silver harp pin Regan had given him onto his jacket and tried to avoid the puddles underfoot. Since leaving the army he hadn’t belonged to anything and was excited to be a Harper and learn what that meant. For now, though, he just had to wait. Regan and Mirt would tell him where to find the wererats in due course. But first he needed to find his friends.   

So the session began with a split party. Alan was heading to find his allies; the last he had heard they were in the tavern frequented by the dungsweepers, the Gentleman’s Rest. However, by the time he got there they had already moved on.

Chasing their tails

For the first part of the session I was flitting between the two groups and, every time Alan thought he was getting close to the others, they went to a new location, or he got distracted.

First, he arrived at the Gentleman’s Rest, only to be told they had left an hour earlier and were heading to another tavern. On the way to the other tavern he rolled on the Nighttime Scenes table of the Dragon Heist DM Screen. He rolled 83, which unbelievably reads, “1d6 giant rats scurry across a street or into an alley. There’s a 25 percent chance that 1d4 of these oversized rodents are actually wererats in beast form. They’re looking for unlocked cellars to plunder and they avoid potential conflict.”

Given Alan’s recent history and obsession with wererats, this meant he spent the next 20 minutes following the rats and trying to see where they went. He was rolling Wisdom (survival) checks each time he found a clue and was doing quite well, nearly catching them at one point. However, he eventually rolled a 3 and lost the trail, but not before passing a suspiciously disturbed sewer grate with some Xanathar graffiti.

The Heist

Meanwhile, after learning a little about the Dripping Dagger—a modest tavern, mostly frequented by out-of-towners (non-humans)—Arvene was waiting outside, as Dugg and Little Joe went in. They didn’t see a single human. There were orcs and half-orcs, bugbears and goliaths, goblins, kenku and kobolds, even a firbolg and a tiefling tending the bar. But no humans. This could work in their favor. After all, the person they were looking for was sure to stand out in this crowd.

Dugg found a table as Joe walked up to bar and attempted to charm the barman, with his wit. A very strong charisma roll (22) while talking to the firbolg let him learn that Brian the human was staying in a large room at the front of the tavern, a room that overlooked the street.

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I quickly sketched out the map so they could visualize the layout—always useful in a heist.

Joe took this information back to Dugg who then took a stroll around the tavern. A poor investigation roll (8) meant he didn’t spot anything unusual as he walked about. Then he rolled a performance check to act casual (17) and leaned inconspicuously on the balcony overlooking the bar.

Outside, Arvene got the signal from Joe to enter and stepped into the tavern. Her arrival was met by fierce stares and grumbles: “What’s that doing here?” “Who let the hooman in?” Two large bugbears were so mad they stormed straight out of the tavern in disgust.

At that moment, Alan arrived at the corner of the street, having given up on the giant rats. He missed Arvene by seconds. He was greeted by two burly, angry, drunk bugbears, who proceeded to push him around. “Stupid human. Don’t you know when you’re not welcome?”

It’s OK, she’s only half human

With Alan occupied outside, Arvene felt all eyes fall onto her. Little Joe jumped on to the the table he was sitting at and yell, “It’s OK everyone, she’s a half-elf. So only 50% human. Don’t worry, she wont infect you.” Only a strong performance roll would let him get away with that. He rolled 22. Everyone settled down in the bar, but tension were clearly still high and Arvene continued to attract many angry stares.

From the balcony above, Dugg saw Arvene sit down at the table and turned to join them. But before he reached the stairs, the door behind him opened. The door they were watching. Out stepped a female tiefling wearing the same uniform as those working behind the bar. She adjusted her skirts and headed down the stairs, pausing only to look in a mirror and try to fix her smeared make-up.

This was what they’d been waiting for. Dugg signaled Arvene and then, without hesitation, threw a beer glass over the banister to cause a distraction. Alan had just entered the tavern at this point and only a dexterity saving throw of 17 let him avoid being hit by the flagon. The Bald bugbear next to him wasn’t so lucky. He didn’t react well to having being glassed and thus began the long-awaited bar fight. My players were so happy to have started a tavern brawl.

Bar Fight!

They used the fight as a distraction to dash up the stairs and break into the room. Arvene was last; she had a plan of her own and disguised herself as the female tiefling who had left the room moments earlier, attempting to trick Brian. At this stage, each player had things they wanted to achieve simultaneously, so the best way to do that was to:


First, Joe cast Firebolt at the door and ran in, only to see another door beyond. Dugg then ran past Joe and smashed door number two. He entered the room and found their mark, Brian, asleep on the bed, unperturbed by the noise and commotion. Arvene and Alan were last in, dashing into the room and slamming the door shut behind them.

Over the course of the next round of initiative, Joe and Dugg managed to wrap up the sleeping man in his own duvet, turning him into some kind of Brian-burrito; Arvene rummaged through the pockets of his clothes; and Alan stood looking confused. He wasn’t really sure what was happening, having joined the party late. “Do we know this man?” he asked. “He is a bad guy, right?”

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While he was wrapped up, Joe managed to intimidate the man-fajita into revealing the location of the sword. There was a chest in the room that Dugg managed to shimmy open, but his own blade snapped in two as he did. Inside the chest, along with Brian’s traveling clothes and dirty laundry, was the magic sword they sought.

Brian was confused; he called out to Arvene to help, “Daisy, why are you doing this? Help me.” Arvene, ever-mischievous and still looking like someone else, replied, “It’s over Brian, I’ve found someone else. Long live the Xanathar.” The Brian-Burrito wilted and began sobbing in Joe’s arms.

Sleeping Brians

The party could hear the brawl still going on in the tavern, and having found the sword, really didn’t want to go back that way. So they decided to exit through the window. Before he leapt out, Joe cast Sleep on Brian, hoping that would keep in occupied for the night and that he would wake up thinking it was all a bad dream.

Meanwhile, Dugg found a quill and black ink and wrote on the wall above Brian’s bed, “Don’t mess with the Xanathar or the pretty lady gets it,” then he followed Joe out the window.

A silver harp

Dugg landed next to Joe on the street outside and they looked around. Good perception checks from them both (16 and 18) meant they saw the two Drow who were watching them from across the road. But before they could run to them, the city watch turned up to sort out the disturbance in the bar. When they turned their attention back to the Drow, they had gone. leaving only a black eye-patch and a packet of playing cards behind.

Arvene finished rummaging through the clothes, she didn’t find anything she liked. But she did find an ornate silver pin, in the shape of a harp. She took it and pinned it to her scarf and followed Joe and dug out the window. A bad athletics check (6) meant she landed heavily and twisted her ankle.

Alan was the last one in the room. He secured the ties around the sleeping man and moved towards the window. This had been a very confusing night for him, and he wasn’t even sure exactly what they’d just done. However, he had recognized the pin Arvene had found. A Harper’s pin. He had a very similar one he’d been given that morning. He hoped Brian wasn’t a Harper too. That would cause all sorts of trouble. END


This was a strange, but very fun session. I hadn’t planned for it to be a full-blown heist, rather just a quick intro to the game followed by the next day’s activities, but my players just went with it and it took the whole session to resolve. This did make fitting in Alan’s activities a bit difficult; I wanted to make sure he could be involved in the action, but didn’t want to have him just conveniently turn up right at the start.

The extra encounter with giant rats in the alley was pure luck as well—there are 24 other night time scenes that don’t involve rats that he could have rolled, but I guess the dice gods had already decided what was going to happen.

I’m intrigued to see what happens with the Harper pin and if Alan comes clean about his joining the organization, or even if Arvene notices he’s got one too. I can see it all getting a bit political within Dragonclaw Inc!

What did we learn?

DM Tip: Read everything before you play, especially the read aloud text boxes and dialogue from your adventure resources. And be prepared for your players to pick up on things you won’t even notice. This whole session came out of one sentence in a supplement I ran last week. Dung Work is a DMs Guild adventure that sees the players take on the roles of Dungsweepers for a few days. One of the encounters in that supplement has them going to a tavern and hearing about a missing magical sword. A thief says: “I unloaded it in Spendthrift Alley to some human. Said he had to go back to his room in the Dripping Dagger to get the gold.” That one section of dialogue was enough for my players to create over two hours of game play, planning, executing, and improvising a heist. None of the NPCs asked or even hinted that they wanted them to do this—in fact when I realized what they were thinking, the NPCs actively tried to convince them NOT to. But that is the nature of the game: 80% of being a good dungeon master is letting go completely of what you planned and just seeing what happens.

Next week the players have their second day of dungsweeping to get on with. Although they might hear a rumor at breakfast about a fairy dragon with a penchant for stealing rainbows and go on an entirely improvised adventure to return sunshine to the Sword Coast. Who knows. I’m only the Dungeon Master after all.

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