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Christopher Robin and his friends make a Christmas list, but Pooh forgets to ask for a present. He must get the letter back and to Santa Claus by Christmas, which happens to be tomorrow.
Tigger doesn't like Piglet's too cute poems, so he adds some twists to excite himself.
Tigger has a problem when a cloud follows him around, constantly raining on him. Gopher tries to help his Grandpappy, but Rabbit tries to save his garden and rutabaga potato from construction of the above-ground underground city.
Gopher buys a steam shovel and is wrecking the forest, so Piglet wants to convince Gopher to stop. It's Pooh's birthday and because the gang doesn't know how many candles to put on Pooh's cake, they come to believe that he is wise.
Christopher Robin runs away from home after his statue is broken.
Christopher Robin assigns Pooh and the gang dogsitters for the neighbor's dog, Skippy. However, when he goes loose, Pooh, Piglet, Tigger, and Rabbit must try to retrieve him before Christopher Robin returns home. Otherwise, he may never get a pet of his very own.
When a toy train goes missing, Piglet has a dream. In his dream, he is the sheriff of a Western town, Rabbit and Eeyore are his deputies and Tigger and Pooh are the Hole in the Head Gang (well at least Tigger is), when out-of-luck Sheriff Piglet takes Pooh in by mistake.moreless
After Christopher Robin leaves for a party, the gang thinks he's too old for them.
Christopher Robin and his pals have a late night adventure.