Baloo and Becky go shopping and Kit is left with the responsibility of babysitting Molly. Kit has his hands full, until Molly's favorite radio program, 'Danger Woman,' comes on. During the commercial break, Molly wants ice cream. They were instructed not to go further then the corner store. Meanwhile, Don Karnage sends Mad Dog and Dump Truck to steal goods from Cape Suzette via sub. When they cut through the net that keeps all sea creatures from entering Cape Suzette's harbor, A giant squid follows them. When Molly's wagon rolls all the way down to the docks, Kit asks Molly not to tell her mom how far away they strayed. However, Becky heard everything and told Kit that he was reckless and irresponsible. But when the apartment building is attacked by the squid and the pirates on the loose, Kit's job of protecting Molly is far from over.

Baloo has to deliver a box back to Cape Suzette before dawn. Since it was only midnight, he decides that he can spend a few hours at Louie's. But panic ensues when the sun starts to rise. He decides to use the excuse that pirates attacked him. Baloo then demonstrates with the Sea Duck how he escaped, but unknowingly loses the box out the back hatch. When he returns to Higher for Hire with nothing, it costs the business $10,000. After promising Becky that he will never again stray from the schedule, he's given a new assignment. Give a tour of Cape Suzette between 11 and noon. While Wildcat is fixing the plane, he runs across the box lodged in the engine. Baloo can still get the $10,000 if it's delivered before noon. Not wanting to go back on his word, he sends Wildcat on the tour while he delivers the box. But when it becomes clear that the box holds a stolen treasure; Baloo has to return the goods, avoid Trader Joe and his goons, and get back to Hire for Higher before noon.

After tricking the pirates, Baloo starts his flight back to Cape Suzette. Over confident, Baloo gets the pirates to chase him through the canyon. However, Air Traffic Control won't clear the Sea Duck because there's a blimp already passing through. Forced to escape the pirates, Baloo sneaks around and safely passes. However, the stunt results in Baloo getting his license suspended for a week. With the need to transport an iceberg to the desert prince, Becky gets a fliers permit and decides that she will fly the plane with the help of her book 'How To Fly In 3 Easy Lessons.' Becky refuses to listen to anything Baloo suggests. After all, he got his license suspended, so what does he know? But when air pirates attack the Sea Duck, Becky soon learns that you can't learn everything from a book in one day.

Becky decides to only charter to a higher class clientele. In order to place her ad, she cashes in Higher For Hire's insurance policy. However, when the clients start asking her if they're insured, she tells them they have 'Collateral Insurance.' When they take off they get the deed to the Sea Duck until the plane, and it's cargo, reaches it's destination safely. If it doesn't, they get to keep the plane. The first customers want to transport a bag full of jewels to their family compound at Hyena's Port. Becky takes the job, but Baloo begins to suspect their appearance may be a front for something else.

Baloo is reacquainted with Ace London, a highly regarded pilot. He belittles Baloo and boasts himself as the ace of the skies. They both have to pick up packages at the same cargo hold. By Ace's ignorance, he picks up Baloo's cargo of pickles and Baloo picks up Ace's cargo: A Top Secret Plane Engine. Upon realizing his mistake, Ace claims Baloo stole his cargo. He then explains the mission to his reinforcements over the radio, which is being intercepted by Don Karnage. When Baloo doesn't respond to Ace, Ace opens fire on the Sea Duck. When he realizes that the whole ordeal is over the fact he has the top secret engine, he has to personally fly back to the military airbase to clear his name.