Running Chaos at the Yawning Portal

Planning the Mayhem

I knew from the start that Session 3 was going to be the moment. The Yawning Portal fight is a classic set piece—part bar brawl, part horror show, part introduction to Waterdeep’s dangerous underbelly. It had to set the tone for the world: beautiful, deadly, unpredictable.

So I asked myself three questions:

1. What’s the emotional arc of the session?
   I wanted tension to rise in stages—from tavern calm to sudden ambush to full-blown Undermountain nightmare.
2. How can I spotlight each player?
   Each character needed at least one moment to shine, whether it was a clever tactic, a botched spell, or an emotional reaction.
3. How do I keep the chaos controlled?
   This battle had two waves of enemies, plus civilians, plus Durnan, plus Fluffy the wolverine. I had to run all that without losing the table’s attention.

I prepped a rough timeline of combat beats, with optional interrupts (like the tiefling girl jumping in the well), so the scene could evolve organically based on player actions.

Executing the Encounter

Once the session started, I leaned heavily into theater of the mind, narrating the tavern’s sights, sounds, and smells. The first few minutes were all banter and slice-of-life. It made the sudden ambush hit that much harder.

Here’s what I found most effective:

• Let the players react first. I didn’t jump into initiative the second the attackers burst in. I described chaos and let them decide whether to hide, fight, or protect civilians. This gave them ownership of the scene.
• Layer the threats. The first battle was classic martial mayhem. Just when they thought they’d won, I hit them with the tiefling’s plunge and the skeletal-winged creature, introducing a shift in tone from crime drama to horror.
• Use Durnan as a safety valve. When the second monster appeared, I could feel the table tense. That’s when I had Durnan leap into the fray. He didn’t outshine the party, but he anchored the scene and showed them they weren’t alone.
• Give the familiar a turn. Fluffy the wolverine had a moment of heroism. It wasn’t a big tactical move, but it added heart and levity. Players love when their animal companions get to be scrappy.

Reflections & Takeaways

What worked:

• Cinematic pacing. The session felt like an escalating action sequence.
• Character spotlighting. Every player had a moment—success or failure—that felt meaningful.
• Tone shifts. Comedy, danger, horror, heroism… all in one tavern. It kept the players guessing.

What I’d tweak:

• I could’ve done a bit more to manage the battlefield geography. Players sometimes had trouble visualizing where they were during the chaos.
• The second monster could’ve used a stronger introduction—maybe a sound cue or player Perception check before it emerged.

Advice for Fellow DMs

If you’re running the Yawning Portal fight (or a big bar brawl in general), here are some quick tips:

• Layer your conflict. Don’t throw all your threats in at once. Build suspense by staging the encounter in acts.
• Use the environment. A bar’s got tables, chairs, chandeliers, drinks. Let players improvise.
• Balance tone with care. Humor and horror can mix brilliantly—but lean too far either way, and the scene loses impact.
• Give NPC allies purpose. Durnan didn’t steal the show—he helped sell the stakes.

Final Thought

This session was a reminder of why I love DMing. Not because everything went perfectly—but because it felt alive. The players weren’t just rolling dice—they were in the Yawning Portal, saving strangers and slinging spells.

And that’s the magic of a good session: players go home with stories to tell, and you go home already planning what horrors are climbing up next.t our heroes? Will they conquer the serpentine horror? Stay tuned for the next thrilling installment of Waterdeep: Dragon Heist!