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While searching for honey, Pooh and his friends embark on an adventure to find Eeyore's missing tail and rescue Christopher Robin from an unknown monster called The Backson.

During an ordinary day in Hundred Acre Wood, Winnie the Pooh sets out to find some honey. Misinterpreting a note from Christopher Robin, Owl convinces Tigger, Rabbit, Piglet, Pooh, Kanga, Roo, and Eeyore that their young friend has been captured by a creature named the Backson, and they set out to save him.—Anonymous

The story takes place inside a book in Christopher Robin's room. Robin has an active imagination and an uncanny ability to collect all sorts of things. His favorite collection are the stuffed animals. Robin and his friends Winnie the Pooh (Pooh for short), Piglet, Rabbit, Eeyore, Tigger, Owl, Kanga, and Roo, all live in the Hundred Acre Wood. Pooh is Robin's best friend, and together they have many unusual adventures in the Hundred Acre Wood. Robin plays in the woods with a red balloon, which is now flying around freely in the forest.

Winnie-the-Pooh (Jim Cummings) is a kind-heart anthropomorphic bear who loves honey. Pooh wakes up one day to find that he is out of honey. Pooh's stomach is rumbling and there is nothing in the house. Pooh tries to get honey from a beehive, but the bees chase Pooh away. While out searching for more, Pooh discovers that Eeyore (Bud Luckey) an old miserable gray donkey, has lost his tail. Eeyore lives in the house that Piglet, Pooh and Tigger built for him.

Pooh, Piglet (Travis Oates) a small cowardly pig and Pooh's best friend, Rabbit (Tom Kenny) a pretentious and strait-laced rabbit who loves planting vegetables in his garden, Owl (Craig Ferguson) an elderly owl who is not as wise as he thinks and tells very long and boring stories about his family, Kanga (Kristen Anderson-Lopez) a female kangaroo, and Roo (Wyatt Dean Hall) Kanga's excitable baby, come to the rescue.

Tigger (Jim Cummings) a hyperactive and brave tiger, has his bouncing fun with the red balloon. Owl suggests writing a notice, offering a large reward to the person who finds the tail, only Pooh makes the signs saying, "A very important thing to do" and nothing else.

Christopher Robin (Jack Boulter) decides to hold a contest to see who can find a replacement for Eeyore's tail. The prize for the winner is a fresh pot of honey. There are many failed attempts for what would replace Eeyore's tail including a cuckoo clock (which crushes as soon as Eeyore sits down), the red balloon (which carries Eeyore into the air), a YoYo (that hits Eeyore in the eye), an umbrella (which opens in the wind and carries Eeyore off), a dartboard (people throw darts at it), miscellaneous toys, a weather vane (stuck by lightning), and a concertina (which makes too much noise). Finally, Kanga suggests that they use a scarf, which unravels.

The next day, Pooh goes to visit Christopher Robin and he finds a note on his door that says, "Gone Busy Out, Back Soon (misspelled as "Gon Out Bizy Back Soon")". Because Pooh is unable to read the note, he asks for Owl's help. Owl's poor reading comprehension skills lead Pooh and his friends to believe that Christopher Robin has been abducted by a ruthless and mischievous monster they call the "Backson" and Owl describes it in a song that is shown in a chalk-drawing.

The Backson is supposed to have a long tail, a hair covered body, 2 horns on his head, a red mop of hair, and a ring of gold in its nose. It smells of monkey's feet and mold, its toes are black, and fur is blue. A Backson sneaks into the library and scribbles in all books, tangles up all the hooks on the Christmas Tree decorations, spoils the milk, stops all the clocks, use horns to put holes in socks, and is probably the reason why Eeyore's tail is gone. The friends blame all their bad habits on the Backson.

Rabbit plans to trap the Backson in a pit, which they think he will fall into after following a trail of items leading to it. Pooh and Piglet dig the pit (actually, Piglet digs and pit and Pooh supervises), while the others gather the items that will attract the Backson. Owl momentarily realizes that Backson sounds a lot like "Back Soon". The friends gather and establish a trail of Backson's favorite items all over the Hundred Acre Wood.

Eeyore got left behind and was wandering around on his own, when Tigger found him. Tigger was hunting for the Backson, as he argued that only Tiggers can hunt the Backson, and he is the only Tigger. Tigger, who wants a sidekick to help him defeat the Backson, recruits Eeyore to be a second Tigger. He dresses up like the Backson and tries to teach Eeyore how to fight. The training was too taxing for Eeyore, who was getting hit more than anything else. Eeyore, who is doing this against his will, escapes from Tigger and hides underwater. Tigger believes that the Backson has taken Eeyore, and he is picking them off one by one.

After a failed attempt to get honey from a beehive, Pooh's imagination combines with his hunger get the better of him. Pooh starts daydreaming that he is rolling in a river of honey, while in reality he has ended up eating some mud.

Later, Pooh accidentally falls into the pit meant for the Backson. The pit had a picnic mat on top, and an empty honey pot to lure the Backson, which lured Pooh instead. At first the friends believe that it is Backson who has fallen into the pit, and they need to now rescue Robin, whom they assume is with Backson. As they approach the pit in terror, they realize that it is Pooh in the pit and not Backson. Rabbit, Kanga, Roo, Owl, Piglet, and Eeyore (who has found an anchor while he is hiding to replace his own tail) try to get him out but fall in themselves. The anchor was too heavy and drags everyone into the pit with it.

Piglet, who did not fall in, attempts to get Pooh and friends out of the pit, though continuously irritating Rabbit with over-interpretations of his instructions. Rabbit wants Piglet to find something long enough to pull them out of the pit. Piglet finds a rope, but then he cuts it into 6 pieces so all 6 of his friends can climb out. Although, by cutting the rope, Piglet has made it useless. Piglet does not know to tie a knot. Rabbit asks Piglet to go to Robin's house to get a jump rope. Now, Piglet was scared to death to travel alone, but Owl flies out of the pit to give him courage, and then flies right back in. Piglet was still very scared traveling through the forest. Piglet finds the red balloon stuck in a tree. Piglet runs into Tigger, still in his Backson outfit, and mistakes him for the actual monster.

Piglet escapes from Tigger on a red balloon, which knocks some of the storybook's alphabet letters into the pit. After the chase, Tigger and Piglet fall into the pit as well, where Eeyore reminds Tigger that he, being "the only one," is "the most wonderful thing about Tiggers". The red balloon escapes from Piglet's grasp and flies out of the pit.

Eventually, Pooh figures out to use the fallen letters to form a ladder, and his friends are able to escape the pit. They soon find Christopher Robin (who was holding the red balloon), and tell him about the Backson, but he clarifies, saying that he meant to be "back soon." Robin explains that the real reason for his disappearance was that he was at school. The prize pot of honey is awarded to the red balloon for finding Christopher Robin. The pot was tied to the balloon which took it higher and higher and out of sight.

Still hungry, Pooh continues his search for honey. He soon visits Owl's house, where he discovers that Owl has been using Eeyore's tail as a bell pull, unaware of whom it belonged to. As Pooh leaves Owl's to return Eeyore's tail, Owl offers him to stay for some honey, but Pooh, ignoring his hunger, declines. As a reward for this act of selflessness, everyone in the Hundred Acre Wood presents Pooh with a giant honey pot, much to his delight.

A real Backson (Huell Howser), who is revealed to be a very nice and gentle creature, discovers the trail of items that Pooh and his friends left and falls into their pit.