dragon heist

D&D Waterdeep Dragon Heist: Session 19

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D&D Waterdeep Dragon Heist Session 19

Dragon Heist

Dragon Heist Session 19: Scrying into His Handkerchief

Not for the first time this week Joe found himself naked in public. As he handed over the pile of his brand new clothes, he paused. “Would you be so good as to provide me a handkerchief to cover my modesty sir?” Regent laughed, but could see no reason not to. With that Joe stood up and without signalling to the others walked speedily towards the exit and out of the Gentle Mermaid. Once again, naked in the street with nowt but his cowboy hat and hanky for cover. But his mission was successful. So far.

Last night was the 19th session in our online Waterdeep Dragon Heist D&D campaign and it was all going surprisingly smoothly, right until the end.

The setup

We have been playing our Dragon Heist campaign 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. We have even been attempting to stream the games live on Twitch—but have been experiencing a fair number of technical and sound issues so far.

dragon heist

This week I even got to use some of my brand new dwarven forge terrain pieces. I was very excited.

dragon heist
Dwarven Forge pieces made the perfect alleyway for the encounter at the session’s finale.

I’ve been supplementing the Dragon Heist campaign book with material available on the DMs Guild. Besides using guides that flesh out the NPCs of Dragon Heist, like Residents of Trollskull Alley and Trollskull Alley a Waterdeep Dragon Heist DMs Resource. Last week, we finished the second of two sessions of an adventure supplement called Dung Work, and this week I found one based on a faction mission from chapter 2 called Scrying into His Handkerchief  and had prepared to run this mini-adventure, which would hopefully take them up to chapter 3 and the next level.

Sadly we were without Dugg, our fighter, this week, as he was busy negotiating a peace treaty between Hyrule and the Mushroom Kingdom. Hopefully next week he’ll return and no more innocent Toads will have to suffer.

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.
Little Joe, Drow Sorcerer – channeling the spirit of John Wayne.

Previously in Dragon Heist

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.

Last session Joe was visited by mysterious haberdasher called JB Nevercott. He had a mission for the sorcerer. More of a test, really. If Joe successfully collected a personal item from the rich nobleman, Regnet Amcathra, and delivered it to a homeless tielfling in the Dock Ward, he would be initiated into a secret organization, granting much power, influence, and beneficence. Joe recruited his friends to assist and they were successful in retrieving a handkerchief from Regnet—although Joe did have to gamble away his clothes to get it. Now they must get to the Dock Ward and find the girl without attracting too much unwanted attention. Easy.

Thugs in Tuxedo

As they left the Gentle Mermaid, Dugg nudged Alan by the shoulder; “That was my cousin in there, Esvele. I’m going to speak with her. I’ll meet you back at the manor.” Joe, meanwhile, naked except for his hat and a nobleman’s hanky, confidently strolled down the High Road ignoring the stares and the sneers of the well-to-do locals. Alan and Arvene followed. Not too closely. Behind them, two burly figures in black suits kept to the shadows, trailing the party.

As we started the session I noted down everyone’s passive perception scores. This had the added effect of putting everyone on edge, “Why would he want to know that?” It soon became very clear. Their scores are: Joe 11; Arevene 13; Alan 14.

With those scores, both Joe and Arvene were far too preoccupied celebrating their success in the casino and awkwardly trying to ignore Joe’s nakedness. Alan, however, did notice the two tuxedo’d thugs who were clearly following the group. Immediately Alan and Joe both start running, but Arvene, still distracted by Joe’s generous handkerchief, didn’t get away before a heavy hand grabbed her shoulder.

A strength contest between Arvene and the thug was a draw (16 vs. 16), so Arvene wasn’t able to get away. Alan and Joe, not noticing Arvene’s predicament, kept running.

“You lot are up to something. What do you want with Regnet?” The burly goliath tried to intimidate Arvene. She claimed ignorance. “I don’t even know who he is,” she lied (22 deception). The thugs believed her and shrugged.

“Stay out of the Gentle Mermaid. I know your face now.” 

Chasso’s Trot

Arvene miraculously managed to get away from the heavies and joined her companions in an alley off from the High Road. She found them searching for ways to clothe Joe in the trash. A mediocre investigation check (17) meant they were marginally successful.

In the alley they discussed their next move and, not for the last time, questioned their alignment, “Are we the good guys?” 

Truth is: there are no good guys in this Dragon Heist campaign.

They decided to head straight to the Dock Ward to try to find Advertence, the deformed tiefling to whom they were tasked with delivering the handkerchief.

Dragon Heist DM Screen

It was getting late as they passed southward through the city, but there was still sunlight causing Little Joe—the darkness-loving drow—discomfort and disadvantage. At this stage Waterdeep is in the middle of summer and people filled the streets, so I rolled twice on the Dragon Heist DM Screen daytime scenes table.

First roll was 71. A mage using a Tenser’s floating disc spell to transport a huge pile of books ran past the party. First the books hovered by, followed shortly by a disheveled wizard (with Wizz’edd written on his pointy red hat), “It’s OK. Everything under control. Pay no attention to the runaway tomes. Situation: normal.”

The second roll was 13. A friendly half-orc asked the characters for directions to a random location in the city. Fortunately for the half-orc, Arvene is a local with a fairly accurate map of Waterdeep. She was able to point the half-orc in the direction of the Gralhund Villa and he hurried off, shouting his thanks and expressing gratitude. “Wow. You guys are so nice. It’s such a relief to meet a bunch of good people in this city.” 

It wasn’t until after the session that the true irony of this statement hit home.

Keel Alley

After a couple of hours traveling south through the city, the party arrived at the familiar outskirts of the Dock Ward. Arvene was consulting her map to see where they had to go and they began questioning locals to try and find the disfigured tiefling. Alan rolled an investigation check (16) and was able to find out that Advertence lived in a crate just tucked into Keel Alley at the corner of Net Street and Dock Street. He also learned that she was believed to have psychic powers and would shout out the fortunes of passers-by. The fact she could shout descriptions of passing strangers despite being obviously blind attracted enough attention and customers to keep herself fed.

Making their way farther south through the Dock Ward, the houses became tenements, then turned into squats, before devolving totally into a shanty town, reminiscent of the Field Ward. As they approached Keel Alley, they could hear voices raised in anger.

You brazen little urchin! How dare you!”

There in the Alley stood two female thugs, dressed like pirates. At first glance it looked like they were shouting at a pile of linen and dirty cloth. Then Alan and co. realized the pile of debris was actually a person. A crippled, scarred tiefling. One of the pirates raised her fist to strike the defenseless girl. Alan was not having that. He threw a dagger and it struck the attacker in the back.


What ensued was a very frantic Alley fight that lasted four rounds. Their aim was not to kill the assailants, and Alan, Joe, and Arvene each landed some pretty good hits. But so did the thugs. They had the stats of Bandit Captains, challenge rating 2 monsters, each with 65 hit points, so at this stage in our Dragon Heist campaign this was not an easy fight.

dragon heist

On the first round Little Joe cast Sleep. This is a spell that affects creatures in a specific area, but they have to have less than a certain amount of hit points left to be affected and therefore sent to sleep. Little Joe rolled 29 and so neither thug fell asleep. Casting this spell on the first round wasn’t very effective, but at least Little Joe now knows how best to use this spell. Once three rounds had passed and Alan and Arvene had a chance to reduce those hit points, it was much more effective and one thug was snoring as they took care of the second.

At the beginning of the fourth round, badly hurt, the conscious thug went to run from the scene. However, she ran straight into the shiny metal breastplate of Hyustus Staget, Captain of the Dock Ward City Watch.

Captain Staget

The cigar chomping captain knew the thugs and was both surprised and pleased to see Alan and crew doing a good deed and coming to the rescue of Advertence. Captain Staget clearly knew Advertence, and expressed his sincere gratitude for saving her.

“I always knew you were good guys,” he said. “Also, thank you for not killing anyone. It really would be inconvenient if I had to arrest you. The paperwork is already pilling up on my desk. What with the Xanathar Guild and Zhentarim war going on. Speaking of which, we must be going. Take those thugs to the clink guys and let’s go.”

Joe’s Choice

Staget left the party in the alley with Advertence. She began making some cryptic comments about their future, “He’s not who you think he is,” she warned, but they didn’t know quite whom she meant. The crew then discussed what they should do next. Little Joe gave Advertence the handkerchief, as per his mission, and Arvene began asking her random questions. Lottery tickets, sports scores, election results, etc.

Alan, deciding that a clairvoyant could be a useful addition to Trollskull Manor, offered Advertence to come home with them, but as soon as he did her manner suddenly changed and she became agitated and fitful. Screaming, “Help! Help! Fire! No not there. Not then. Beware the flames!”

Her screams grew louder and showed no sign of abating. She took on an almost demonic visage. Alan, turning to Little Joe, and fully intending him to cast Sleep once again said, “Take care of her,” before grabbing Arvene and dashing to the entrance of the Alleyway.

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 it would 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. END


Oh dear. That is not what I had expected to happen. After a session of doing good deeds and having NPCs praise them for their positive actions, I did not see Little Joe making such a dark decision. I think both Arvene and Alan’s players were both in total shock too. However, neither of their characters actually know what happened. So, unless Joe mentions any different, they should assume that he simply put her to sleep and left the alley as Alan intended him to do. The ramifications of her doing otherwise will certainly be severe. Dragon Heist is a campaign where you really have to keep the locals on side. There are multiple NPCs deeply invested in the disfigured tiefling including JB Nevercott and Captain Staget, as well as plenty NPCs which my players don’t yet know about. Yet.

What did we learn?

DM Tip: Keeping secrets from players isn’t always easy. But if you are able to withhold just enough information to keep them interested, drip feeding them little by little, it can really add a sense of satisfaction and accomplishment keeping players invested in the narrative. Advertence’s backstory (not in the Dragon Heist campaign book, and entirely taken from the supplement) is particularly interesting, and if they had asked, either Captain Staget or Advertence could have told the story of how she ended up living in a crate in the Dock Ward. However, they didn’t, so I resisted the urge to wax lyrical, and hopefully this lack of knowledge will spur them on in future sessions to explore her story further.

Next week in our Dragon Heist campaign, we find out how Little Joe deals with his new dark secret. Will he tell his companions what happened in the alley, or will his actions eat him up from inside, corrupting his soul until he explodes in a furious ball of guilt? Either way, there’s bound to be some very unhappy people on Waterdeep, once the truth is discovered.


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