Solo FLAIL - The Flying Lootsman

May 10, 2026

If you are party of my normal gaming group, don't read any further! Not until after our gaming getaway weekend, anyway!

Setup

In the Hammerhead Tavern in the city of Bruhl, our misfit guild of adventurers takes a dismal breakfast of gruel and watery mead. In the midst of their meal, shouts of fear and chaos arise outside. Rushing to the streets, the party sees everyone looking up to the sky, and following their gaze, sees far overhead a flying wooden pirate ship, trailing a long banner with words written on it in bright crimson: "Nice Wallz!"¹

Gun ports open up on the side of the flying ship and cannons point downwards, but instead of cannonballs launching at the city, bright red gouts of flame fire on the rooftops, setting buildings ablaze from high above. A stack of papers is thrown off of the ship, fluttering slowly to the ground below. On each is an identical copy - a ransom note, demanding ten thousand gold coins to leave the city alone.

Gund, the dwarven warrior and self-proclaimed leader of the crew, gets a desperate, greedy grin on his face and turns back to his crew. "We're gonna capture that ship!" Glazbad, the half-orc cleric and Nahar, the human Bone Whisperer, exchange a look of shared annoyance at their leader's insane ambitions, while Ember, kobold druid, plays with a bit of shapeless fire in his scaled hand and nods along with Gund.

After a trip to their guild tinker, an elderly gnome with a penchant for insane stunts, the guild crams four "volunteers" onto a rickety glider (a contraption that will surely only carry them one-way) and before the sun has risen to noon, they run themselves off a tall building and into the sky, pursuing their flying prize.

A Few Notes About Tools

The purpose of this little solo adventure was to learn FLAIL!, a fantastic new hacky-slashy brawler of an OSR game. It's truly delightful, with a variety of tones, a simple but satisfying character creation process, and above all, an emphasis on getting into the game quickly and going. I found this to truly be the case here.²

I spent about the same amount of time in character creation as I did setting up character traits for Triple-O, which is the emulator that I used here to determine what the party does. This allows me to run this game as the GM, so that I can play published modules with full knowledge, yet still be surprised and delighted at the outcomes and emergent narratives. This is largely driven by character traits and a simple dice system for determining party decisions. You'll see me refer to this in my sidenotes as Obvious, Option, and Odd - the Triple Os!

Finally, I'm playing through The Flying Lootsman ³. I'm running this next weekend for my normal gaming group, so a big motivation for running this solo is to familiarize myself with the module, the new system, and character creation so that I can have a very smooth, fun experience with my gang.

Play!

On with the show!

The wings of this makeshift glider vibrate, rattle, and instill a deep respect for mortality in its occupants as it carries them through the updrafts. After a few minutes, they are gliding above the wooden pirate ship, but with only the barest ability to control the glider, all they can hope for is a crash landing that leaves them on the deck somewhere.

They aim the glider at the main deck and dive towards it.⁴ It races up to meet them, and sure enough, the glider slams into the wooden planks of the main deck, wings crumpling and ripping and wooden beams snapping as they tumble head over heels. Before they can so much as regain their balance, a horn blasts from the bowsprit that hangs in the sky over the front of the ship, and a dozen stunned pirates draw blades and surround the party.

Ember notices that some of the pirates are looking up in fear and trepidation, and trains her eyes skyward to the crow's nest, which ironically is occupied by a gigantic Roc. At the moment, the Roc seems content to sit her nest, and doesn't move nor take interest in the goings on below. But Ember calls this out to Gund.

Gund is however, too eager to shed blood, and draws his magical blade, Coral Whisper. Pale pinks and seafoam green, pocked with marks like eroded stone on an isolated beach, and somehow always dripping with salty water, the blade glistens in the sunlight as he shouts a warcry.

More pragmatic, Glazbad utters a pray to Zor'Vol, demon lord of Chaos, and surrounds the group in an inky black cloud of darkness⁵. Nahar, now in his element as a summoner of dead and dying things, begins a chant that grates on the ears of all that hear it. Even the other members of the crew are filled with a sense of despair, and after a moment, every single living thing on the deck starts to feel their life draining out of them. As the chanting continues, the dozen pirates on the deck fall to their knees, and then their faces, and crumble into papery, lifeless husks. ⁶

As Glazbad releases the cloud of darkness and it dissipates in the wind, Gund turns angrily to Nahar. "You wretched bastard! I told you at the Craven Temple to never use that around us again!" Nahar shrugs slowly, the evil smile never leaving his lips. "I saved your hide, dwarf. You're welcome." Gund grips the hilt of his magical blade tightly, taking his anger out on the leather wrap, before scowling and pointing to the rear of the ship. "Captain's quarters will be on the aft castle. Let's gut the cretin and take over the ship."

The party marches up the wooden steps to the quarterdeck, where the main helm sits. The helm is a stylized scorpion's tail, where the wheel sits on the tip of the stinger. A beautiful and terrifying piece of woodwork. Off to the side of the ship, hanging over the edge in the open air, is a bird cage - but, rather than a colorful parrot or elegant cockatoo, inside that iron cage is a mangy, half-thing of flesh and feather. Terrifying to look upon, the party quickly turns their back to it to focus on their work. The door to the captain's quarters is here, and after a cursory check, it's clearly locked.

Glazbad, the half-orc covered head to toe in burn scars, turns his permanent scowl up toward the poop deck one staircase up. "We should check up top. Cover our backs." His gruff voice is the one that Gund listens to the most, although none of the rest of the guild could say where this respect comes from. They certainly don't get treated the same way by the self proclaimed guild master. While waiting for Gund to realize the wisdom of his words, he takes a moment to pray for divine health from Zor'Vol.⁷ Lifeforce, however twisted into the mockery of life that Zor'Vol represents, flows into Gund, replenishing what was drawn from him by Nahar, who skulks behind the group.

On the poop deck, the highest deck of the ship, is the rusted but functioning machinery that ends in a mechanical claw. The claw is currently holding the unfurled banner that taunts the city below. Glazbad, always curious about machinery, wanders over to look at the controls. Ember says, "Just bash the thing a few times, turn it off, and let's go kill the damn captain." The two argue back and forth about whether to use it or destroy it, until Gund snaps at them. "We don't have the rotting time to mess with this right now! Nahar, come over and fiddle with this thing. If you can't figure it out, we're moving on."

Nahar fiddles with the levers and buttons for a moment.⁸ The whole clawed hook mechanism shakes side to side as he discerns what each movement does. Eventually, he finds the combination of inputs that opens the claw, and opens it, and the huge banner falls away, flapping in the whipping wind, descending onto the city below. A cheer is raised on the ground, the sound barely making it all the way up to the ship. Nahar scowls at the celebration.

Gund leads the crew back down the stairs to the quarterdeck. He spots the door to the captain's cabin and points his sword at it. "We break it down?" He asks nobody in particular, before throwing his shoulder into it.⁹ The door which cracks and caves in slightly, and then a second shoulder check bashes the door in. Inside, seated upon a gaudy makeshift throne in a room that was clearly meant to be a bedroom, is the imposing figure of the kobold Captain Skarx. Orange scales marked with scars, including a vicious horizontal scar across the snout, below the eyes. A docked ear is adorned with gold rings. Not a very large creature, but a wicked face and a wicked twin bladed axe convey his malicious intent.

Skarx tries to put on a face of benevolence and magnanimity, but the result looks more like constipation. "Come on then, boyos... isn't there an arrangement to be made? After all, we're all civilized folk here... there are rules for this sort of thing on the open sea!"

Ember squawks from behind Gund, "We're scraaak not on the sea!"

Gund rolls his eyes, puts his palm on Ember's forehead and shoves him back behind the others. "I'll make a deal... so long as it results in you being elsewhere and us taking this ship!" Greed plays across his eyes, flecks of gold swimming in black oil.¹⁰

GM Note: Doubling down in Triple-O means rolling 2 d6s instead of one and choosing your favorite option. If you roll doubles, you take that action with emphasis, and reinforce whatever tag, trait, ability, or story element guided that decision. It's a way of introducing character development based on action - How wonderful!

The captain's overly friendly guise drops instantly, replaced by a sneer. "This here is my boat, and I'll see you off of it!" He whips out a liquid filled device from behind his back and points it at the crew, and a gout of liquid flame flies out and fills the room.¹¹ Glazbad dives behind a piece of furniture in the room which is set ablaze, and his jacket catches fire in the process. He flails his arm around trying to put it out, and his skin, already covered in burn scars, aches with remembered pain.¹²

He growls from the pain of it but puts it out from behind cover, then grabs his sword, the wondrous blade Coral Whisper, pulling it from its sheath. Its length, pink and teal in oceanic motif, almost seems to bear moving waves of water, a trick of flickering firelight. With a barbaric howl, he charges the captain, and the rest leap forward to join him. Combat!

Gund shouts out some orders, and the group move into thoroughly practiced formations and orders of operation. Gund launches himself at Skarx to try to disarm him of his handheld flame cannon. He slashes across Skarx's arm with Coral Whisper, causing Skarx to shout in pain, and the flame thrower drops to the wooden floor.¹³ Glazbad, shaking off memories of his traumatic past, charges in with his flail and connects with Skarx's torso with a sickening crunch. Immediately, Skarx begins to panic. "Grolg! GROLG! Where are you, you buffoon? Grolg, GET IN HERE!"

Skarx stumbles over to the wall and pulls his double bladed great axe off of its hooks, bringing it chopping downwards toward Gund's head, but he misses terribly from the pain and shock that he's in and the blade of the axe drives into his own foot, pinning him to the floor.¹⁴

Gund guffaws at the kobold captain's buffoonery. "This is the great and terrible captain that was going to ransom all of Bruhl? Lads, he's pinned himself with his own axe!" Gund howls in laughter and the rest of the guild lower their weapons and join in the laughter. Gund tilts his head at Nahar, who nods and walks up to the captain. Nahar puts his mouth close to the captain's ear and whispers quietly.

"You may yet live... if you and your crew... disembark. Immediately."

The captain, wailing in pain from his injured foot, starts sobbing and blubbering and collapses into a heap, still pinned by his own axe. The crew finds a set of manacles and shackles Skarx to his own desk. Glazbad grabs the Fire Thrower that Skarx dropped, while Ember searches for prizes in the rest of the room. She discovers a beautiful golden broach in the shape of a scarab, and a workable length of cord.

The guild, leaving the pathetic kobold captain shackled in his own quarters, heads back out to the deck to begin removing the rest of the pirate nuisance from their new ship. As soon as the door opens though, the enormous Roc in the crow's nest flaps its wings, lets out a deafening SKRAWK and swoops down to attack the guild!¹⁵

See you in part 2!