Unearthing the Under-Hollow Order: A Shadowy D&D Organization Born From a Player’s Backstory

Unearthing the Under-Hollow Order: A Shadowy D&D Organization Born From a Player’s Backstory

November 24, 2024

Have you ever had a player come to you with a backstory so juicy, so loaded with hooks, that you couldn’t help but spin it into an entire campaign arc? That’s exactly how the Under-Hollow Order was born in my kids’ D&D game. This sinister, subterranean organization crawled out of the shadows of a single player’s story and grew into a full-blown campaign threat—and now it’s ready to slither into your game too.

The Origin of the Under-Hollow Order

It all started with a player character named Sylparin, a curious half-elf with a penchant for making questionable deals (and ignoring good advice). Sylparin’s backstory featured a surrogate father figure, Graycight—a former member of a mysterious shadowy order who was on the run after uncovering their dark secrets. That was all I needed. I grabbed that thread, gave it a firm tug, and the Under-Hollow Order unraveled onto the page.

In our game, the Order became a serious threat after Sylparin decided he needed to find his lost friend. The friend was stuck in a secretive cabal of shadowmancers and planar manipulators who hide their operations deep underground, working to twist the balance of light and dark in the multiverse. With their penchant for secrecy, they fit perfectly as an antagonist for any party stumbling upon forbidden knowledge.

What is the Under-Hollow Order?

The Under-Hollow Order is an organization devoted to studying and exploiting the power of the Shadowfell. Think of them as shadowy academics with a side hustle in world domination. They believe that shadow is the ultimate force of creation and destruction, and their endgame is to collapse the Veil—the boundary between the Shadowfell and the Material Plane—so they can rebuild the multiverse in their own image.

Their headquarters, the Under-Hollow, is a labyrinthine fortress hidden deep underground. It’s part monastery, part research facility, and part prison, where they conduct their experiments and guard their darkest secrets.

Key Leaders of the Under-Hollow Order

Every villainous organization needs a cast of characters to make your players shiver. Here’s the roster of the Order’s heavy hitters:

Grynesolite (Gryne) – The Shadowed Sovereign
The Order’s supreme leader, Gryne, is as enigmatic as they come. Few have seen their true form, as they project an illusory shadow of themselves that looms over the Order’s ceremonies. Gryne’s mastery over shadow magic makes them nearly untouchable—physically and politically. Gryne’s ultimate goal? Collapse the Veil and reshape reality itself.
Valthin “The Iron Warden” – Head of Discipline
Valthin oversees the Order’s prisons, including the grim Umbra Vaults, where traitors like Graycight end up. A towering figure with a literal iron mask fused to their face, Valthin ensures that no one escapes the Order’s grasp.
Niratha Darkwhisper – Master of Secrets
Niratha is the spider in the web, responsible for espionage and information control. She commands a network of spies, both magical and mundane, and is always ten steps ahead of anyone who threatens the Order.
Kaenith the Profane – The Shadow-Touched
The Order’s top researcher, Kaenith, experiments with shadow magic, often at horrifying costs. His body bears scars and mutations from his “successes,” and his creations include shadowforged constructs and cursed relics.

How to Use the Under-Hollow Order in Your Game

The Order is incredibly versatile as a villainous organization, whether you want them to be a constant looming threat or the secretive puppeteers pulling strings behind the scenes. Here are some ways to incorporate them:

The Main Campaign Villain: The Order’s goal to collapse the Veil makes for a perfect campaign-long arc. Players can uncover their schemes one by one, learning about their experiments, their agents, and ultimately, the Shadowed Sovereign’s true plan.
A Shadowy Side Quest: Maybe your party finds an ancient journal (like Sylparin did!) or an artifact bearing the Order’s sigil, leading them to a forgotten ruin or a hidden outpost. What they discover there could be just enough to make them a target of the Order.
Personal Stakes: Tie the Order to a player’s backstory, like I did. If one of your characters has a past linked to forbidden magic, planar travel, or a missing family member, the Order can serve as the sinister connection.

Hooks and Intrigue

The Journal of Glazaen Shadowbender: A key item for my players, this lost journal belonged to Graycight (real name: Glazaen Shadowbender). It contains cryptic notes about the Order’s hierarchy and experiments. What else might it reveal if properly decoded?
The Shadowforged Key: A mysterious blackened key, rumored to unlock not just doors but entire planes. What happens if the players bring it to the Obsidian Gate at the heart of the Under-Hollow?
The Umbra Vaults: A rescue mission to free someone imprisoned in the Vaults could bring players face-to-face with Valthin and expose them to the horrors of the Order’s secret experiments.

Why I Think My Players Will Love This Arc

There’s something inherently thrilling about an organization like the Under-Hollow Order—it’s full of secrets, shadowy rituals, and moral gray areas. Here’s why I think my players will dive headfirst into this arc:

Personal Stakes: The Order isn’t just another group of bad guys—they’re tied to one of the party’s own, which makes every encounter with them feel deeply meaningful. Sylparin’s connection
The fifth edition Dungeons & Dragons Dungeon Master’s Guide describes “The Shadowfell, also called the Plane of Shadow, is a dimension of black, gray, and white where most other color has been leached from everything. It is a place of darkness that hates the light, where the sky is a black vault with neither sun nor stars.” [Image courtesy Wizards of the Coast]
to Graycight and the Order’s dark secrets gives the players a built-in reason to care.
Mysterious Villains: Who doesn’t love peeling back the layers of a secretive cabal? The Under-Hollow’s leaders aren’t straightforward enemies—they’re complex, each with their own motives and methods. Figuring out how they operate and what they’re hiding will keep the players on their toes.
High-Stakes Drama: The Order’s goal to collapse the Veil between the Shadowfell and the Material Plane raises the stakes from the get-go. It’s not just about stopping a bad guy—it’s about preventing a cataclysmic event that could reshape the entire multiverse.
Epic Locations: Exploring the Under-Hollow itself will be an unforgettable adventure. A sprawling underground fortress full of shadow-infused magic, experimental horrors, and mind-bending traps? Sign me up.
Moral Quandaries: The Order isn’t evil for evil’s sake—they have a philosophy. Some of their members might believe they’re doing the right thing, or they might offer the party temptations to join them. What happens if the players start to question who the real bad guys are?
Player Freedom: Whether my players want to infiltrate, destroy, or even bargain with the Order, the arc leaves room for them to take the story in the direction they want. Maybe they’ll decide to rescue Graycight, or maybe they’ll aim to topple the Order entirely—it’s up to them.

I think the mix of mystery, danger, and personal stakes will hook my players and create moments they’ll be talking about long after the campaign ends. Now I just need to set the stage and watch the shadows come to life!

What about you? Are there any shadowy organizations lurking in your world that your players haven’t encountered yet? Let me know—I’d love to hear how you plan to unveil them!

Thanks for reading. Until Next Time, Stay Nerdy!