Rabbit attempts to get Tigger out of the way while he harvests by inventing up a bouncing bunny relative of his and daring Tigger to bounce Castle Ridge by giving him “miracle” shoes. Then it gets out of hand.
Tigger starts the day doing what he does best which is bouncing! Rabbit is planting cabbages and doesn't want Tigger to bounce him. He gives Tigger the challenge of bouncing Castle Ridge, an extremely high ridge. Tigger is upset that he can't even make it with his "bestest" bounce. He begs Rabbit to help him. Rabbit says he's related to the best bouncer in the world, The Awesome Bunny of "Upsy Dasia", and agrees to 'help' Tigger.
Rabbit gives Tigger the 'shoes' of the 'awesome bunny.' He gets Gopher to help him, however he quits when Rabbit puts metal and screws in them to weigh Tigger down. Tigger then tries to use the shoes to bounce Castle Ridge. Rabbit says he just "has to get used to them" and Tigger practices nonstop to bounce with the shoes on until he is exhausted. Rabbit is upset when no one thinks his joke is funny.
Piglet misunderstands Tigger when he explains where he got the shoes from and thinks it's the "Awful Bunny of Upside-Downsia". Tigger, unwilling to give up the shoes until he reaches the top of Castle Rock in one bounce, then starts sleep-bouncing in his house and through the woods at night, covered in his blankets, and Rabbit tries to get the shoes back before it's too late. Piglet is scared when he thinks the awful bunny is in the woods and thinks he wants the shoes back, but Tigger doesn't want to give them back until he bounces to the top of the ridge. Piglet, Pooh and Rabbit camp at Tigger's house. Pooh comes armed with his pop gun to scare the awful bunny away.
That night, Rabbit gets the shoes off Tigger's feet, but when he tries to get rid of them, Tigger sleep-bounces him and bounces off into the night. Pooh and Piglet think the awful bunny took him, only to discover that the "awful bunny" is Tigger, who managed to jump Castle Ridge in one bounce while sleeping. Rabbit throws the shoes down Gopher's hole. Gopher comes up with them and lets the cat out of the bag. They discover that Rabbit was lying to Tigger the whole time. Tigger however, is happy because he thinks that Rabbit helped him build up his muscles. Tigger says he had heard about a cow who jumped over the moon and wants to surpass it in bouncing over the moon. Rabbit faints, which Tigger attributes to excitement as the episode ends.