The movie opens with a view of a boy's bedroom, with assorted toys and books scattered around. The narrator tells us that it is the room of Christopher Robin, and that he likes to collect things. He mostly likes to collect stuffed animals, and his favorite is Winnie the Pooh.
The movie shifts to animation, with the pages of a book, and illustrations of the 100 Acre Wood, where Winnie the Pooh and his friends live. The page turns, and it is "Chapter One: "A Very Important Thing to Do". Pooh is sleeping and the narrator calls his name to wake him, but he is talking in his sleep about honey. Pooh finally wakes up and his stomach growls-he says it is rumbly for honey and, "A Pooh bear takes care of his tummy". He looks all over his house, but all the honey pots are empty. So, he leaves to go find some honey from one of his generous friends.
Pooh finds Eeyore, and asks if he has any honey. Eeyore doesn't have any, but as he checks, Pooh notices that Eeyore's tail is missing. Owl is up above them in the tree, writing his personal memoirs, and Pooh asks him if he could take a break and help them find Eeyore's missing tail. Owl suggests that first, they must issue a reward for the finder of the tail. Pooh says "G'blesh-you" and asks if he is sick. Owl is confused, and Eeyore confirms that both he and Pooh heard Owl sneeze. He thinks they are silly, and he did not sneeze. They get back to discussing Eeyore's tail, and when Owl mentions they need to issue a reward, both Pooh and Eeyore again think he sneezed. Eeyore also thinks that he is catching whatever Owl has, and has a scratchy throat. Pooh tells him that honey is good for a scratchy throat. Owl finally figures out that whenever he said "issue", they thought he said, "achoo", like a sneeze. He reassures them that he isn't sick, and explains what "issue" means. They agree that Christopher Robin needs to write and hang the notices about the missing tail and reward.
"A Very Important Thing" signs go up, and all the animals in the 100 Acre Wood show up for a meeting. Tigger bounces in with a red balloon, and the static from it makes the balloon stick to his fur, which scares him at first. He sings his, "I'm the only one" Tigger-song. At the podium, Christopher Robin informs the animals of the tragedy of the missing tail. There is a contest to find the best replacement tail for Eeyore, and the winner will get a pot of honey. With honey as the reward, Pooh is thinking and thinking of what would be a good tail for Tigger. He runs home and comes back with his cuckoo clock. They stick it on the nail in Eeyore's bum, and proclaim that it is a fine tail, and Pooh wins the honey. They sing the honey-winner's song, and as Pooh is about to eat the honey, Eeyore sits down, and the cuckoo clock shatters. So they take the honey back, which saddens Pooh, and all start trying other tails. Piglet brings the red balloon over, but it lifts Eeyore's hind legs up and tries to fly away. Then they try an umbrella, dartboard, misc toys, but none will work. Kanga brings over the scarf she has been knitting, and places it on Eeyore's nail. He likes it, and they proclaim her the winner and start singing the honey-winner's song again, but she asks them to PLEASE not sing it again.
Pooh's tummy keeps rumbling, so he leaves to find some honey, as it is now past breakfast and nearly lunch. He finds a red string on the ground, and follows it, and eventually finds that it is Kanga's scarf. It has gotten stuck on something and come unraveled, so Eeyore is still in need of a tail. They walk back home and find a note form Christopher Robin: " Gone Out. Bizy. Back Soon". Pooh cannot read it as he says he is a bear with very little brain, and so he takes it to Owl to read. Owl invites him in, and offers him some honey. As Pooh stretches up to he shelf to reach the honey, his tummy stitches pop, and his stuffing falls out. He puts it back, but before he can eat the honey, Owl is worried about the note: He reads it as Christopher Robin has been captured and being held by the "BackSoon" . He describes him to Pooh as a huge creature with horns, a ring in his nose and a pointy tail. He's the creature that scribbles in your books, tangles the hooks in the Christmas decorations, and puts holes in your socks. A terrible creature such as this means they need to go rescue Christopher Robin.
The friends come up with a plan: they will dig a deep hole, and fill it with things the BackSoon would like, and then he will fall in it and be captured. They dig, and bring lots of toys to fill the hole. Pooh covers it with a picnic blanket and Piglet puts large rocks on the corners. They hope they can lure the BackSoon there and he will fall in. Piglet brings a honey pot and places it in the blanket. Pooh opens it to eat it, but it is empty. Piglet explains that it is just for the disguise of tricking the BackSoon. The animals dress up with pots, pans or even an oven mitt on their heads for protection, and begin to leave a trail of toys through the woods, to lure the BackSoon out. Tigger, however, has another plan: he thinks they are too slow, so he dresses up like a BackSoon, and goes into the woods to track him. He finds Eeyore, who has been left behind as he was too slow to keep up. Tigger says that the two of them will go track the Backsoon together. First, he tries to "tigger-ize" Eeyore: he paints Tigger-stripes on him, and adds a spring for a tail. He tries to teach Eeyore to bounce likes he does.
Pooh spies a beehive but it is too high to reach. He places Piglet on the low end of a teeter-totter and then he jumps on the high end, sending Piglet soaring up into the tree, but he is shot right into the beehive, head-first. Pooh tries to get his head out of the beehive by hitting the hive with a stick, and Piglet is worried. The bees inside don't seem to like that. Pooh keeps hitting it, and the angry swarm of bees comes out and chases them. Pooh says, "Run!" and they run smack into Rabbit. Rabbit takes the hive off poor Piglet's head, and throws it up high into a tree, and the bees go back in. Pooh asks Rabbit, "Please, Rabbit, can we eat?" as his tummy is rumbling loudly, but Rabbit says not until they rescue Christopher Rabbit.
All Pooh hears is honey-honey-honey whenever anyone says anything-he is so distracted by his hunger that he can't think of anything else. Rabbit suggests that he try to think of something else, like finding Christopher Robin. He sees a honey pot, and runs for it, and falls into a deep hole before he can grab it: he has just fallen into the BackSoon trap. Pooh moans, as he is stuck and cannot get out. The animals hear the scary moan, and think they have caught the BackSoon. Afraid, none want to check, but they finally do and are surprised to see Winnie the Pooh in the hole. Eeyore comes over and has an anchor on as his tail. All the animals fall in the hole and are stuck. Piglet is topside and tries to help them out. He looks for help, but no one is there. He cuts a long rope into 6 small pieces, one for each animal, but the pieces are too short to reach into the hole. Rabbit tells him to knot the rope, but he says he cannot. Rabbit remembers that Christopher Robin has a rope in his room, and sends Piglet to go get it. He is scared to go into the woods by himself. He goes, and gets frightened by the shadows there. He sees that one of the shadows is just Tigger's red balloon, stuck in some branches. He pulls to get it out, and bumps into Tigger in his BackSoon disguise, and freaks out and runs away, thinking the BackSoon is there to get him. They run and fall into the hole. Pooh sees the red balloon floating above, and takes the letters from the story and stack them into a letter-ladder and climbs out of the hole. The rest of the animals do the same. They hear a noise and are frightened that it is the real BackSoon, but it is just Christopher Robin. They are happy he is safe and ask how he escaped the BackSoon? Christopher Robin has no idea what they are talking about, so they show him the note. He explains that they just mis-read the note, and that it said that he was "busy" and will be "back soon".
For finding a way out of the hole and saving the day, they award the honey pot prize to...the red balloon. Pooh just says, "Oh, bother". He walks to Owl's house to hear him read and have that long-promised taste of honey and sees a sign, "Don't Knock-Please Ring", so Pooh pulls the ringer for the bell, and stares at it. Something about it is very familiar: he remembers! It is Eeyore's missing tail! Owl said he found it in a thistle bush. They take it to Eeyore, and he says he was fond of that tail. So they all go to Christopher Robin, so he can reattach the tail. They ask Eeyore if he is happy, but he says, "No. But I sure do like this tail".
As a surprise, Christopher Robin gives Pooh a GIANT pot of honey as a reward. He explains that he really did a "very important thing" as he thought of his friend instead of his tummy. Pooh climbs up the sides of the pot, climbs in, and closes the lid. He swims in the honey and eats large handfuls. Christopher Robin smiles and says, "Silly Old Bear".
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