The Caverns of Midnight’s Fools: A D&D One-shot

“The first yugoloths were created by a sisterhood of night hags on Gehenna. It is widely believed that Asmodeus, Lord of the Nine Hells, commissioned the work, in the hope of creating an army of fiends that were not bound to the Nine Hells. In the course of making this new army, the hags crafted four magic tomes and recorded the true names of every yugoloth they created, save one, the General of Gehenna. These tomes were called the Books of Keeping. Since knowing a fiend’s true name grants power over it, the hags used the books to ensure the yugoloth’s loyalty. They also used the books to capture the true names of other fiends that crossed them. It is rumored that the Books of Keeping contain the true names of a few demon lords and archdevils as well.”


Continuing my notion of ‘what if players were monsters?’, I created another one-shot adventure this week. This time, I turned my attention to players being able to adventure as either a demon or a devil.

In the mythology of Dungeons & Dragons, demons reside on a plane called the Abyss whereas devils occupy the Nine Hells. The two evil factions, one chaotic and the other lawful, have been engaged in a feud called the Blood War for eons. The Blood War is ongoing but seems to be at a simmer at the current moment. Between these two factions of fiends is a third, the yugoloths who reside on the plane of Gehenna and the Blood Rift (a space between the Abyss and Nine Hells), are neutral evil, and independent of any godhead.

I thought they’d make a perfect fit for players for several reasons. First, they’re rare. I would imagine only experienced players have every faced off against a yugoloth in their various campaigns simply because there are so many other fiends (devils and demons) to choose. A new or middling experience player might not ever encounter one and part of why I’m making these one-shots is so players can experience monsters as monsters.

Second, yugoloths are tough. There are four types of described in the fifth edition of the Monster Manual with Challenge Ratings of 5, 9, 12, and 13. Their resistances, immunities, default telepathy, and unique spellcasting make them formidable. Coming up against one (or many) ought to be the domain of only high level players, but playing as one of these fiends, well, that sounds badass.

Third and lastly, these fiends aren’t beholden to any god. They exist as mercenaries looking out for themselves alone with no compunction for taking on any kind of job. It’s difficult to play an evil character, but it’s easy to play an amoral egoist (I assume). Built into these fiends is a literal devil-may-care attitude as they can’t truly die if they are on the material plane and only prize their independence to continue to fuck things up as they themselves see fit.

So, my premise was simple…

“A Book of Keeping has reportedly been acquired by a cult of Asmodeus on the material plane. They plan to use it to summon Yugoloths to serve them in the name of Asmodeus. The mysterious General of Gehenna as telepathically contacted a party of Yugoloths and tasked them with discovering if the report is true, and if so, retrieve it and destroy the cult.”

This Book of Keeping holds the true names of every yugoloth in existence allowing whomever has the book to summon and control the fiends. The General of Gehenna will not allow this to happen so it sends a party into the myriad depths of the caverns called Midnight’s Fools. With no fear of true death on the material plane and honored the mysterious General of Gehenna would choose them, the party of yugoloths are focused on rooting out the cult.


Throughout the caverns lurk other dangers as well as a rival party trying to get to the Book of Keeping first. The arch-devil Levistus, imprisoned by Asmodeus in ice for a past betrayal, has gotten wind of the book’s existence as well and has sent a party of his devils to retrieve it. Levistus believes with the book, he can strike down Asmodeus thereby freeing himself from his icy prison and take over the Nine Hells.

So I created multiple options for players. They can play as one of the four types of yugoloths or as one of four types of devils (Ice Devil, Horned Devil, Bone Devil, or Barbed Devil). It’s up to the DM if the party will encounter the rival group of fiends, however, I also set up the adventure so that players could face off against each other. The adventure can be run for up to 8 players–2-4 yugoloths vs. 2-4 devils.

Whatever route the players choose, their goal is to find the cult’s leader, Strada Sunstrand, an elven warlock who has devoted his life to the service of Asmodeus, in possession of the book. But to get to Sunstrand, the party will first have to find their way through the caves wherein they’ll encounter kobolds, exiled fomorians, chuul lurking, vicious trolls, and a spectator driven mad by its isolation.

I hope players find this adventure challenging and engaging, a change of pace. DriveThruRPG wouldn’t allow me to make this available, you download it here:


The Caverns of Midnight’s Fools


I’d love to hear any thoughts about the adventure. I plan on writing one more one-shot where players get to adventure as monsters.

7 thoughts on “The Caverns of Midnight’s Fools: A D&D One-shot

  1. Hi there Daniel! I am part of large group of D&D adventurers, and preparing my first DM campaign. Possibly wont be for a while so I have a lot of time to make my caverns but I wanted to thank you for sharing your campaign. I am basing mine on your Cavern of Midnight’s Fools and having the basic story as you have written it. Some of the enemies will be the same but I have added some different caverns and the end goal to reach the book of keeping from the cult is as you have written it. I think it is a great idea and I wanted to do a campaign where the players are not normal heroes and as I was definitely wanting to limit their outside world interactions (my groups have a habit of of going off to areas the DM has not planned for so a dungeon is definitely what I was after!)
    We have a website where we upload our stories and blog on all things D&D that is currently being revamped as I am now making a range of table top gaming accessories and we are dedicating more time to our world of Dungeons & Dragons.. You will be credited for this campaign and if acceptable to you, I will be including a link to your site?
    I will be updating the website with my prep so far over the weekend and then add to it at various stages and then of course once it takes place, upload the diary with pictures etc.. I would love for you to have a look as it progresses.

    1. Well, this made my day. Glad to hear you’re interested in the campaign idea, & I’m jazzed to see how you conduct it and players react. Let me know if you need a hand or whatnot–I’d love to be a resource!

      1. Hope I do it justice – a bit worried that it is a bit of big starter campaign for DM virgin but I am so excited. Your concept is just great and when I mentioned it to my players they are very excited to play the non – heroes. Thanks for your support, I may well ask for advice. I have made the pages live now so you are credited and links are there for your page. x

      2. Aces! I followed your page & read what you’ve put down. Feel free to email me or whatever if you want any help.

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