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Two days before Christmas, Christopher Robin writes out a letter to Santa Claus for him and his friends in the Hundred Acre Wood, asking for the following presents:
Rabbit wants a new fly swatter to use against the bugs who constantly invade his garden
Eeyore wants an umbrella to prevent snow from falling on his house
Tigger wants a snowshoe so he can bounce in the snow
Christopher Robin wants a sled "big enough for me and maybe a friend or two"
Piglet said Santa Claus could bring whatever he wanted.
He sends the letter off into the wind, but the next day (Christmas Eve), Winnie the Pooh realizes, after Piglet informs him, that he did not ask for anything himself, so they go find the letter, which has not gotten very far. Afterwards, they, along with Tigger and Eeyore, go to Rabbit's house and rewrite the letter to include what Pooh wants (a pot of honey, of course). Along the way, though, they become greedy and start upgrading their desires (Rabbit wants a bug sprayer, for instance).
Following this, Tigger, Eeyore, and Rabbit go off to get a tree big enough for "the stuff we're gettin'", with help from a reluctant Gopher (he is supposed to be hibernating). In the meantime, Pooh and Piglet go back to the point where Christopher Robin sent the letter and cast it off into the wind again. But the wind shifts southward, and the letter follows Pooh all the way to his house. Knowing that the rest of the gang will not get their presents as a result of this, Pooh takes it into his (and Piglet's) hand to make sure the gifts are delivered.
Disguised as Santa, Pooh sneaks out and delivers Tigger, Rabbit, and Eeyore a super-bouncer barrel, a bug sprayer, and a mobile home, respectively - or rather, handmade versions of said items that break apart upon use. Demanding to know what is going on, the three of them corner "Santa", who insists that he is who he claims to be. But then, Piglet (disguised as a "sorry-lookin' reindeer") slips and makes his sled fall downhill, thus loosening Pooh's disguise.
After explaining what happened, Pooh decides to try to deliver the letter to Santa by himself, leaving the rest of the gang behind to wait up for him. He does not get far, though, as the wind suddenly takes the letter, so he gives up and goes back to the gang. Even after he tells them that he failed in bringing the letter, though, they are happy to have him back, because they have realized what Christmas is really about. Afterwards, Christopher Robin shows up on his new sled and brings them the gifts they had originally asked for. Everyone is happy except Pooh. But then giving Christopher Robin a hug he gets very happy.