D&D Waterdeep Dragon Heist: Session 10

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Waterdeep: Dragon Heist

Session Ten: Making it up as I go

Mirt twirled his mustaches and gave a smile that showed all his pearly white teeth. “Ever since that lazy dullard Durnan got his own place I’ve been thinking of running a tavern myself. Now you’re telling me I can, but without the glass-cleaning and chair-stacking that old fool is spending his days with. Count me in! Now, here are my terms…”

Last night was the 10th session in our online Waterdeep Dragon Heist D&D campaign and it didn’t turn out how I planned at all.

The set up

We are playing via Skype 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 Skype account so that I can stream battle maps for encounters; this has proven quite successful and came in handy once again last night as my players explored a whole new area of Waterdeep.

I’ve been using a couple of additional resources from the DMsguild for my sessions as I mentioned last week, but this week’s session was almost entirely improvised. And not how I intended the session to go. Luckily I had the Dragon Heist DM Screen to hand. In fact, I used it multiple times to help steer the adventure. What do the adventurers see in the street? What trinkets do they find in enemies pockets? What’s the name of that tavern? It’s all on the screen.

Dragon Heist
The Dragon Heist DM screen came in handy this session when improvising a quest in the Field Ward

I also got a chance to use my Wall of Fire and Wall of Ice which made me very happy…

Dragon Heist
I saw these used on an episode of Critical Role and knew I needed them immediately

…and these cool condition markers that I bought from a seller on Etsy.

Dragon Heist
I couldn’t recommend these condition markers highly enough. I now own three sets…

The party:

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

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

Previously in Waterdeep

Alan, Dugg, Joe, and Arvene met in Waterdeep and formed a small independent investigations company called Dragonclaw Investigates. Their first mission was to save Floon Blagmaar who had fallen victim to the Xanathar/Zhentarim war that was raging on the streets of the city. Not paid for this as they had hoped, they were offered the deed to Trollskull Manor instead. The party accepted and found themselves in possession of a large house in the North Ward that is in desperate need of renovation.

Last week, after a fracas in the street with some buskers, the heroes entered their new house and met Lif, the not-so-friendly ghost that lives there. In order to appease him, they’ll have to restore the place to its former glory, so they set off to see Mirt “the Moneylender” to raise some funds. Only problem is he wanted a share in the business, 5% of the profits for every 100GP he gave. They needed at least 1,000GP and so were looking at giving Mirt 50% of their profits. There must be another way to raise some cash…

Don’t get bit

Mirt talked quickly and in intricate circles that seemed deliberately to contradict and confuse. None of the adventurers were able to keep up, but wisely didn’t allow themselves to be committed to any contract. He was impressed with their caution; most people who come to him are more desperate and willing to bargain their souls. Mirt did offer to send ’round a surveyor in the morning, so they could get a clear idea of the amount they’d need—“Cole Clambertop, best in the business.” He also advised of a couple of alternative avenues for funding.

And with that, they got up to leave Mirt’s office. As a final thought, Alan asked Mirt if he had any little jobs that a team of security enforcers could pick up to secure a bit of coin. He did. This is where the improvisation began, and where I started to dig a hole for myself.

“Looking for extra work are ya? Sure, how well do you know the Field Ward? There’s a tavern there, run by a half-orc named Mistress Hamshackle. Owes me 300 dragons. There’s 10% in it for you if you can liberate the monies. The Field Ward’s pretty lawless mind, you watch you don’t get bit.”

Dungsweepers Guild

Before heading off to the Field Ward the party wanted to go back to Trollskull Manor, partly to drop off their valuables before heading into the Wild West of Waterdeep, and partly to deposit Dugg, who wasn’t playing last night.

Dugg’s player had suggested that Dugg would be investigating the plumbing and sewerage of the Manor and liaising with the Dungsweepers Guild to discuss the garbage collection. Although his player was absent, this lead onto a lengthy discussion regarding the guilds of Waterdeep and Dugg became enrolled in the Dungsweepers Guilld. I’m sure his player won’t mind, and will probably try to change the organization from the inside. He’s very environmentally conscious will be keen to see that Waterdeep does its bit to prevent further cataclysmic climate change across Toril.

More street performers

After a brief encounter with Lif, their resident poltergeist, and a basket of animated bread rolls, they set off for the Field Ward. Along the way they spotted the same group of Halfling street performers that they had seen, and assaulted, last session. The Appleblossoms were putting on a performance of “Not Welcome Here,” a Punch and Judy-style farce about a group of incompetent adventurers who move into a nice neighborhood and upset the locals. The crowd were thoroughly enjoying it.

This encounter was the result of rolling 89 on a random encounters table on the Dragon Heist DM screen. It just so happened that they had previously had an encounter with a troupe of Halfling performers. As they passed, Arvene and Alan just about managed to stop Little Joe from throwing more rocks, and they quickly moved on, dropping a couple of silver coins in the hat as they did.

Guards at the gate

The Field Ward isn’t an official Ward of the city and technically isn’t part of Waterdeep. Beyond the main walls, it is a lawless town populated by refugees from around the Sword Coast. It’s a muddy mess without the amenities and guilds that the rest of Waterdeep relies on. Eventually the party arrived at the gate to this area and they could already tell the Dungsweepers Guild didn’t operate here.

Two dwarf city guards were checking carts and taking papers of those allowed in and out, they scoffed at the sight of a Drow as the party approached. It took some convincing to let them out and ensure they would be allowed back in. But Arvene cast Guidance on herself to give her +4 to her next ability check and then rolled a natural 20 for persuasion. This excellent roll meant Arvene was very convincing. One dwarf even offered to take her out for dinner, before directing her towards the tavern they were looking for. It was called the Hart’s Head—another useful piece of information from the Dragon Heist DM screen—and wasn’t too far away.

The Hart’s Head

They got to the Hart’s Head just before midnight and saw it was more of a shack than a brick-and-mortar tavern. There were two saloon doors at the front and smoke rising from the chimney. But otherwise there were no signs of life or activity.

They decided to scope out the area. Little Joe and Arvene checked the perimeter while Alan approached the front doors. As he walked round the rear of the tavern, Little Joe bumped into a Halfling boy; the boy hissed at him and ran off. Joe thought nothing of it.

Alan pushed his way dramatically through the swinging saloon doors and entered a decrepit, broken tavern room. Like their manor, it had smashed chairs and tables about the place and broken glass crunched underfoot. There was a bar at the far end, which he gingerly approached. “Hello? Mistress Hamshackle?” he called.

In response a rasping voice hissed from behind the bar. “She’s not here. Go away.”

Alan refused, instead insisting the owner of the voice show themselves. Suddenly a figure leapt up from behind the bar and landed on it, crouching on all fours. Another Halfling, her clothes were tatty and ripped and her matted hair hung over her face. She hissed at him through pointed teeth and Alan noted her snout-like nose as she said, “I warned you. Hamshackle’s gone. Unless you want to meet the same fate I suggest you leave.”  

Again Alan refused. Then, from seemingly out of nowhere, two more ragged Halflings appeared, flanking Alan. They were clearly looking for a fight, so Alan decided to beat them to the chase. He struck out with his shortsword and slashed across the chest of one of the advancing foes.

“That’s it then,” hissed the first Halfling. “Looks like dinner is served. Get him, boys.”


I was still improvising at the session at this stage, and hadn’t thought about what might happen if there was a fight, so I quickly sketched a tavern on some gridded paper, and flicked through the Monster Manual for the correct page. Thankfully my players all rolled higher initiatives than the Halflings, so that would give me a little more time to think.

Dragon Heist

Alan went first and slashed again with his shortswords; he hit the same foe twice, and then called out to his allies outside. Little Joe ran into the bar and cast Minor Illusion, mimicking the sound of the city guards’ bell. He was trying to scare the foes, but rolled a critical failure on his deception, and they laughed at his paltry attempt. Then it was Arvene’s turn, she charged in behind Joe and cast Sacred Flame.

On their turn, the Halflings retaliated. One missed Little Joe with his dagger, while the other, far more badly hurt one, went for Alan. He knocked him to the ground and lunged at his chest. The female Halfling, clearly the leader, stayed crouched on the bar, hissing and snarling at her fellow thugs.

Another round of combat saw Alan roll a critical fail on his attack and drop his weapons, falling prone on the floor. Joe cast Burning Hands, hitting all three enemies with decent fire damage, and Arvene started swinging her mace. The enemies fought back and one showed his true nature and tried to bite Alan. Alan rolled well on his constitution saving throw and avoided contracting lycanthropy. This is a good thing.


By this point, my players had sussed that the Halflings were wererats. The rat-like features, the pointy noses and teeth, and the biting, gave it away. Little Joe’s fire spell had also caused one of them to partially shift into hybrid form—half rat/half Halfling, hence the biting.

One more round of combat saw the hybrid foe killed. Seeing this the remaining two both transformed into tiny rats and bolted for holes in the walls.

The fracas over, it was clear neither Mistress Hamshackle, nor Mirt’s 300 dragons, would be found this night. The wererats had really spooked the heroes; Alan was scratching his arm where that one had bit him, and Arvene and Little Joe just wanted to go home. It would be long walk back to Trollskull Manor. As they passed through the gates back into the city thick plumes of black smoke rose from the Field Ward behind them. If Mirt couldn’t have that tavern, no one could. END


I enjoyed this session, although the thought of improvising a longer game makes me very anxious. I just hope it hasn’t de-railed the main campaign too much. I also enjoyed including the Halfling wererats, and I’m looking forward to using them again later in this chapter. It was unintentional, but I’m pleased to have foreshadowed their appearance later on.

Our Earth Genasi, Dugg, couldn’t make it last night due to work commitments, so they did not join the party on the exploration. This was part of the reason for the improvised story. I didn’t want them to miss out on any of the key story beats for the campaign, but I might have ended up opening a whole new can of worms instead.

What did we learn?

DM Tip: Improvising can quickly get out of hand. Try to keep in mind what your goals are for the story, who the main factions involved might be, and what their motivations are. Stupidly I did none of these things and have ended up with a convoluted web of intrigue that doesn’t yet lead anywhere. Why did the wererats take over the bar? Why did Mistress Hamshackle owe Mirt money? Who’s behind all of this? I’m hoping my players will fill in some of the gaps for me, and I’ll just go with whatever they think is happening. Sometimes as DM, you just have to cede control.

Before we play each session I write out a very simple flow chart of where I think the session will go, last night we didn’t even get past the first step.

Next week hopefully the party is back to full strength and the party can return to trying to raise the funds to renovate the manor. That is, if they don’t upset the surveyor or accidentally burn it down.

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1 thought on “D&D Waterdeep Dragon Heist: Session 10

  1. Thank you for sharing! I’m looking forward to your next session, so that I can get inspiration for my own campaign.

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