Running a Dungeons & Dragons campaign is always a balance between planning the road ahead and embracing the surprises that arise once the dice start rolling. Session 15 of our Waterdeep: Dragon Heist campaign — which I titled “Riddle, Root, and Flame” — was a perfect example of that balance.

This session had two major beats I wanted to hit:

1. The continuation of the Trollskull Manor mysteries through Lif’s haunted ledger and the riddle hunt.
2. The first truly spectral combat encounter in the manor, culminating in the appearance of the troll specter and its skeletal allies.

What follows is how I prepared these threads and how they unfolded at the table.

Preparing the Session

When I designed this session, I wanted to reinforce the tone shift that’s been building since the party moved into Trollskull Manor. On the surface, they’re fixing up an old tavern. Beneath that surface, however, the manor is steeped in ghost stories, riddles, and the lingering malice of old tragedies.

• The Ledger Riddles: I created Lif’s ledger as a magical object that would guide the party through a series of riddles tied to locations in the manor. Each clue was designed to lure them into exploring the forgotten corners of the house. This kept the session atmospheric while still giving them tangible puzzles to solve.
• The Attic Haunting: I wanted the attic to feel like a climax to these investigations — a cold, eerie space where the ledger’s magic, the manor’s history, and the troll’s skull would converge. The troll specter encounter was planned as a hybrid between a haunting and a combat challenge. Mundane weapons would be less effective, forcing the party to rely on magical means, creative thinking, and sheer persistence.
• The Urchins’ Role: From the beginning, I’ve wanted the Urchins (Nat, Jenks, and Squiddly) to be more than background color. They’re growing into sidekicks and partners. This session was a chance for them to step forward — with Nat in particular landing real combat blows against the skeleton specters.

How It Played Out

The session began with lighthearted moments: the pigeon from the Emerald Enclave crashing into the window with a quest invitation, Squiddly’s gleeful admiration when the bird pooped on someone, and Clover’s earnest (but hilarious) attempts to “activate” the ledger’s brass key by rolling dice over and over. This balance of humor helped set the stage before the tone shifted darker.

Once the group decided the riddle pointed to the attic, exploration took center stage:

• Raven unearthed a lightning-struck twig in the fireplace, a small magical touch that delighted the player.
• The library revealed only mold and decay, but it underscored the age and neglect of the house.
• The rocking chair in the bedroom provided just the right amount of is this haunted? tension before they pressed on.

Then came the attic. As planned, the temperature dropped and silence fell. The troll specter rose from the skull, flanked by skeleton specters. What I loved here was how the players immediately noticed that steel wasn’t cutting it — Doc’s axe passed right through the ghost. This shifted the fight into a puzzle of its own, as they leaned on Raven’s eldritch magic, Clover’s support, and Maple’s druidcraft while the Urchins darted in with unexpected heroism.

Nat’s double-dagger strike was a highlight, both for the dice rolls (two solid hits) and for the narrative payoff. The Urchins are no longer just comic relief; they’re part of this adventuring family.

The fight resolved with the specters defeated and the troll’s skull collapsing back into silence, leaving the manor eerily still once more.

Reflections for DMs and Players

Looking back, this session worked because it struck a balance between planned beats and organic play:

• The riddles and spectral combat gave structure, ensuring forward momentum.
• The players’ humor and improvisation added levity, keeping the horror elements fun instead of oppressive.
• The Urchins became active participants, shifting from NPCs to beloved allies.

For DMs: don’t be afraid to let your mysteries unfold slowly. The ledger riddles didn’t have to be solved all at once — each one deepened the players’ sense of place. And the combat worked better because the players had to figure out what worked; limiting the effectiveness of mundane weapons forced them to think differently.

For players: embrace the story beats even when they’re strange. The pigeon message, the key warming up in Clover’s pocket, or the rocking chair creaking on its own — those are all moments that turn a game night into a memory.

Closing Thoughts

Riddle, Root, and Flame was a session where mystery, humor, and horror all collided. The tavern grew stranger, the Urchins grew braver, and the party took their first real step into the darker heart of Trollskull Manor.

Next time, the consequences of the Enclave’s quest in Undercliff will come to the forefront. But for now, the manor has reminded the adventurers — and me as the DM — that Waterdeep’s stories are never just about taverns and treasure. They’re about the secrets that linger in the walls.