As of this writing, my megadungeon group are on the cusp of Level 17. They’re pretty badass at this point, sitting just a hair’s breadth from 9th level spells, capstone abilities, and the apex of their hard-won feat chains. They enjoy throwing their weight around in local politics, not to mention the local dungeon. They usually get away with it too. There aren’t many creatures in the bestiary that stand up to such legendary warriors, and the legendary warriors in question know it. That’s why I enjoy watching when one of those creatures does show up.

So no shit there they were, seeking for mystical keys sprinkled throughout the upper reaches of the megadungeon. They’d managed to track one all the way back to Level 10, a full six levels below their current APL. Wandering monsters are a joke at that point, and any traps that may have reset are more of an irritant than a danger. Despite all that, I was on the edge of my seat when they finally found the sigil they’d been looking for. It was only partially visible, sticking out from beneath an impressive set of golden doors.

“Wait a minute,” they said. “Isn’t this the lair of that asshole gold dragon?”

“Red dragon,” said the party cavalier. “Remember? We found out that he’d been cursed with a palette-swap. Wish I knew that before I let him geas me.”

Indeed, they’d run into this particular big bad over two years ago IRL. The party had a nice Bilbo-meets-Smaug chat at the time. The cavalier agreed to run some info-gathering quests for the “goodly beast,” then they decided to let the big fella sleep. The revelation of the dragon’s true nature was more recent, and here at last was an excuse to pay back the deception.

“Alright guys. It’s high time we got rid of this punk. We’re way overlevelled. We got the tools and we got the talent. Let’s get some gold dragon boots!”

They knocked. The doors parted. The party wizard tried desperately to keep a straight face.
You may recall that they were level 9-10 last time they’d faced this particular creature. No one managed to make their “identify monster” check back then. The wizard had done so now. The party was facing a CR 21 wyrm.

“Guys?” said the wizard. “We’re just here to pass some info along to the cavalier’s great and powerful patron, right? And we humbly apologize for taking so long to do so, don’t we?”

It was a desperate attempt to use Bluff to pass a secret message: “Do not go through with the attack.” The rest of the party got the message. Unfortunately, with his +42 Sense Motive, so did the dragon.

As a GM, I absolutely live for these moments. Watching my super-powered PCs quail beneath the dragon’s amused regard was supremely satisfying, not least because the moment was so long in coming. I have no doubt that they’ll plot and plan and come back with a proper posse next time. But for purposes of today’s discussion question, what do you say we talk about similar moments in your adventuring careers?

Have you ever realized that you were outmatched? Did you manage to talk you way out of the combat? Did you retreat? Die gloriously in hopeless battle? Tell us all about your most unfortunate boss monster moments down in the comments!


EARN BONUS LOOT! Check out the The Handbook of Heroes Patreon. We’ve got a sketch feed full of Laurel’s original concept art. We’ve got early access to comics. There’s physical schwag, personalized art, and a monthly vote to see which class gets featured in the comic next. And perhaps my personal favorite, we’ve been hard at work bringing a bimonthly NSFW Handbook of Erotic Fantasy comic to the world! So come one come all. Hurry while supplies of hot elf chicks lasts!