Piglet, feeling sorry for Eeyore, who always seems to be depressed, convinces the others to spend a whole day trying to cheer him up.

Rabbit rescues a little bird named Kessie and finds himself in the role of parent. His overly-protective tendencies cause trouble when Kessie begins to feel an urge to fly, which Rabbit expressly forbids for fear of losing her.

Tigger encourages Christopher Robin to clean his messy room by throwing everything he owns under the bed. This proves troublesome when the gang discovers that the evil Crud and his sneezing minion, Smudge occupy a land beneath the mattress and plan to spread messiness everywhere.

All the honey in the Hundred-Acre Wood has disappeared and it appears to be the work of a Heffalump and a Woozle named Heff and Stan. When the gang successfully recovers the honey, Stan decides to get backup in the form of a giant Woozle named Wooster--but Pooh's offer of friendship provides a surprising resolution to the conflict.

When Rabbit forces Tigger to have a bath, the bounce-happy tiger's stripes come off. The gang believes that this "new" creature isn't Tigger, as all Tiggers have stripes, prompting an identity crisis in the sad tiger. Eventually, Eeyore solves the problem by pointing out that it is Tigger's heart, not his stripes, that make him who he truly is.

When Christopher Robin shows Pooh a wishing star, Pooh tells Piglet, Tigger and Rabbit about it, and they all wish for something. But, when Pooh thinks he wished out the wishing star, and that the others' wishes will not come true, he tries his best to fulfill them all.

When Rabbit takes Gopher's flashlight without asking, Gopher panics and he and the rest of the gang go in search of it.

When Owl reads a thrilling mystery novel to the gang, Tigger inadvertently helps him find his lost glasses, prompting the bird to declare Tigger a detective. The bouncy tiger likes the idea, but resorts to committing crimes in secret to give himself cases to solve, which leads to attack of conscience when Pooh is accused of stealing honey.

Rabbit makes a law that there will be no more Valentine's Day after everyone has received countless valentines in previous years.

Rabbit builds a fortress to prevent anyone from trampling into his garden only to realize that he has forgotten to put a door, thus trapping himself inside.