|“Misfortune's Keep. The most feared pirate ship that ruled the high seas, taken down by Captain Soto and his Destiny's Bounty at the end of the era of the Stone Warrior.”|
|— Cyrus Borg|
While working on several projects, Monk began work on the Misfortune's Keep as one of his most prominent creations alongside the Destiny's Bounty. After being fused with his tools and a monkey into Monkey Wretch by Nadakhan, he quickly finished the ship and set sail with the Djinn, with the Misfortune's Keep as their chosen vessel.
- It has a lantern with a map to Tiger Widow Island.
- Oddly enough, tied to the front of the Misfortune's Keep was a sentient, legless pirate skeleton, originally being present during the Misfortune Keep's humbler origins and keeping track of the crew members' stories. The reason for this is never addressed, though it is possible that he is a Skulkin that had either been imprisoned or else inducted into the Sky Pirates as an official member.
- The Misfortune's Keep, as a boat and airship, uses cannons as weapons, as it has hundred of them.
- Under Nadakhan and his crew's command, the Misfortune's Keep became the most feared ship to sail the Endless Sea, rivaled only by its sister creation, the Destiny's Bounty.
- Upon Nadakhan's return, it was converted into an aerial VTOL (vertical takeoff and landing).