In the Hundred Acre Wood, Winnie the Pooh wakes up with an insatiable craving for honey. After failing to find any, he comes across his friends Tigger, Rabbit, Piglet, Kanga, Roo, and Eeyore, who has lost his tail. Pooh and his friends embark on a quest to find a suitable replacement tail for Eeyore, offering various objects in an attempt to cheer him up. Along the way, they are sidetracked by a note left by Christopher Robin, which Owl misinterprets, leading them to believe their young friend has been captured by a creature called the "Backson." The group decides to set a trap for the Backson, hoping to save Christopher Robin and prove their bravery.

Soon, the characters each face their own challenges, and Tigger even creates an alter-ego to help capture the Backson. Misadventures arise as they try to work together, each bringing their unique quirks and personalities to the task. As they navigate through their fears and misunderstandings, the friends discover valuable lessons about teamwork, friendship, and the simple joys of life. The journey strengthens their bonds, reminding them that their close-knit community can overcome any obstacle, even if it's just their vivid imaginations that have created the problem.