A Tyrant in the Caves of Chaos

28 Nov, 2025

B2: The Keep on the Borderlands is a wonderfully customizable module. There are tons of fantastic takes on its content out there, the biggest inspiration for my own take being Prismatic Wasteland's The Keep on the Borderlands is Full of Lies a post challenging the core assumptions of the adventure, if not of old-school fantasy roleplaying as a whole. As my typical process for running an adventure is to strip out as many plot elements as I can to better fit my campaign setting, the Caves of Chaos were a perfect anchor for the first half of my old-school-inspired Pathfinder 2e hexcrawl¹.

My home campaign setting, the world of the Department of Adventuring, is a bureaucratic parody of fantasy roleplaying, the key inspirational anchor points being Terry Pratchett's Discworld, Terry Gilliam's Brazil, and a decent serving of some 90s JRPG for good measure, so right off the bat I knew I couldn't play this straight². As one of the higher-level anchors of my world was a devilish weapons merchant, I decided to continue down that chain and throw some cunning Devils in my Caves of Chaos for good measure.

In my world, the Caves of Chaos are a slummy apartment complex managed by a powerful Devil landlord. Chased out of human civilization, orcs, goblins and all other "monstrous" species retreat to the vast, dark forests. On the coldest, most desperate night, the shivering and starved creatures are approached by a tall seemingly-humanoid woman with a thin smile and a strange red glint in her eyes and offered shelter and community...for a cost, of course.

The Keep has been lost long ago, taken by the ever-expanding forests. The Landlord's right-hand-man, an 8-foot tall bearded devil built like a professional wrestler, runs a gladiatorial arena out of the ruins of the Keep, staffed by bugbears and frequented only by denizens of the Caves of Chaos. The house, of course, always wins.

Crushed by exorbitant rent and gambling debts, the inhabitants of the Caves resort to raiding merchant caravans, burglarizing houses on the outskirts of human civilization, and performing odd jobs for the devils³ to keep their place in their squalid Caves.

Taking this approach to the Caves has had some major benefits in my game:

1. It's an easy seed of conflict for faction play. Every group reacts to the authority of the devils in a different way. The gnolls have a cult-like obedience. The goblins want to rebel and break out on their own, but are stamped down by the hobgoblins, who are playing nice with the devils for now, but plan on pulling a Starscream at the first opportunity. The bugbears are mostly ambivalent and will side with the highest bidder. The orcs are torn apart by conflict; do they attempt to continue the legacy of their old warchief, now retired to live in solitude, or do they embrace the new leadership?
2. It produces a moral quandary around killing the inhabitants. How guilty are these "monsters" if they've been forced into crime by their circumstances? Are the inhabitants who enjoy their work more deserving of crime than those who look upon it with hesitation?
3. Big bad guys rule. My players are currently planning on going from cave to cave, seeing who they can turn against the devils, planning on eventually sieging the Keep with an army of "monsters", and if it all works out for them they'll feel like heroes. Inciting a rebellion is always a good time for your players.

While the idea of a "landlord" obviously won't fit everyone's game, I encourage you to consider adding a Tyrant to your next run of B2. I've been having a ton of fun with it.