Years prior, Kit Cloudkicker was delivering a box containing the Stone of What Was for F.O.W.L., until he is attacked by Don Karnage and his Air Pirates. He manages to evade them, but the stone's magic causes a chicken and goat to fuse; scaring Kit and causing him to drop it somewhere over the ocean. In the present, Della, Huey and Dewey are searching for the stone with the latter learning to fly the plane. Despite Dewey's insistence of wanting to be flashy with his flying, Della and Huey insist that he fly the plane normally. In a last minute effort to show off, he lands the plane, but damages it.
They arrive at Higher for Hire where Della vaguely recognizes Kit from flight school. Kit, initially known as Skydancer, was a master at cloud surfing and was also friends with another student named Molly Cunningham whom Della does remember, but Kit seems reluctant to talk about. Dewey immediately shows an interest in wanting to cloud surf, despite clearly lacking the skill to do so, and Della brings up his missing cargo from years ago. Kit reluctantly agrees to help and the Ducks reluctantly choose to go in Kit's plane, the Sea Duck, as Dewey damaged their own.
It quickly becomes apparent that Kit is a lousy pilot (he uses a crowbar as a "co-pilot" for example) and Della is forced to fly the plane. In the meantime, Dewey asks to be taught cloud surfing by Kit, only for him to have terrible coordination. They are spotted by Don Karnage, who had sent his pirates to go searching for the stone, and attacks his two "greatest arch-enemies". Kit is forced to take over cloud surfing, which Della recognizes as being remarkable, and the group escape Karnage and land on the island where the stone is supposedly located.
The group is immediately attacked by rhino-monkey hybrid who they manage to evade before encountering Karnage and his pirates trying to take the stone. The stone's powers cause the pirates to fuse together, but allow Kit and the Ducks to try and take it, though they are thwarted by Kit's inability to steal their plane and Dewey's incomitance with the cloud surfing. Della ends up awakening a bear-butterfly hybrid who entangles the stone with rope and flies off with it along with Della. As everyone takes to the skies, Dewey refuses to give up on cloud surfing, only for Kit to not only agree that he is awful at it, but that he himself is not a good pilot; having become one because he thought he was destined for it. Huey convinces them to stick with what they are good at.
As the "bearterfly" takes off with Della and the stone, Dewey, now flying the plane, arrives in the nick of time to rescue her. Kit cloud surfs and defeats Karnage and the pirates by destroying their planes. They collect the stone and free the bearterfly before heading back to Higher for Hire. Kit bills the Ducks for the trip and reveals that the bank is going to sell his business. Unfortunately, he is too late, but discovers that it was sold to Molly Cunningham, now a stunt artist named Danger Woman, She offers to hire Kit as she needs a co-star and he agrees, with some support from the Ducks who tell him that he is still bad at flying a plane.
In the middle of the ocean, Karnage solemnly sings about another failure when he sees a piece of the stone, which was chipped off when the Ducks were getting it back from him, and plots his revenge.
- Danny Pudi as Huey Duck
- Ben Schwartz as Dewey Duck
- Paget Brewster as Della Duck
- Adam Pally as Kit Cloudkicker
- Jaime Camil as Don Karnage
- Eliza Coupe as Molly Cunningham
- Kimberly D. Brooks as Peg Leg Meg, Hard Tack Hattie
- Sam Riegel as Pirates
- Kit CloudKicker's voice actor Adam Pally previously worked on the Disney XD animated series Randy Cunningham: 9th Grade Ninja as First Ninja's squire, Plop Plop.
- Adam Pally and Eliza Coupe are from American television sitcom series Happy Endings.
- This episode aired on the same date as the series finale of Tangled: The Series. Coincidentally, this episode aired a year after that show's finale.
- An instrumental version of the TaleSpin theme song is played during the Higher for Hire commercial. As well, it was played throughout the whole episode where Kit defeats Don Karnage and Molly encounters Kit.
- There are several scenes in the Higher for Hire commercial that are a nod to the TaleSpin intro.
- Baloo's fullname from the episode "The Balooest of the Bluebloods", "Baloo von Bruinwald", is mentioned in this episode.
- Like her mother, Molly claims ownership of the Sea Duck.
- This is a nod to the series premiere episode "Plunder and Lightning" from Talespin. Kit being unable to pay back the bank for the Sea Duck and Molly purchasing it is similar to Rebecca purchasing the Sea Duck after Baloo could not pay the bank back in time.
- There were three references to the Disney show "The Wuzzles"
- Like in TaleSpin, Kit uses a crowbar wedged into the flight stick as an autopilot.
- The nickname that Kit uses for Dewey "Little Britches" is the same nickname Baloo used for him in TaleSpin and Mowgli in The Jungle Book.
- Don Karnage claims he's afraid of both bears and bugs when the bearterfly shows up, but Kit is also a bear (and he references this fact) but Don does not appear to be afraid of Kit.