"Eeyore's Tail Tale" is the first segment of the eighth episode of the second season of The New Adventures of Winnie the Pooh. It is loosely based on one of the original Winnie the Pooh stories by A.A. Milne.
While Rabbit's fighting with the bugs, Eeyore thinks they're dancing at a party, so he dances on Rabbit's Bridge leading to the garden and his house in the hopes of joining in, but his tail comes off when he trips on it. Fed up with his tail, Eeyore decides to stop wearing it. Eventually, Rabbit finds Eeyore's tail, and not recognizing it, tries to ward off the bugs, with the bugs falling in love with it. Meanwhile, Tigger convinces Eeyore to get his tail back, but they can't find it, and Tigger concludes it's been stolen and subsequently dons his "Private Ear" cloak and hat to solve the case. Rabbit, labeling Eeyore's tail as a "Worm Wrangler" and mounting it on a fishing rod, makes a little boat with a shoebox and two cones, and dresses Eeyore's tail as a female bug to get them over to the dock. Rabbit then pushes the boat off down the stream, ridding him of his bug problem. Pooh then comes and says hello, and seeing Eeyore's tail, takes it after Rabbit says it's not important. At that moment Pooh leaves Eeyore and Tigger arrive, asking Rabbit what he did with Eeyore's tail. Rabbit then notices his "Worm Wrangler" is gone and tigger, not realizing the two items missing are one and the same, decides to find them both.
Meanwhile Pooh thinks Eeyore's tail is a bee tickler, and uses it to tickle a bee. As Pooh takes a handful of honey, it annoys the bees and Pooh gets knocked off the tree, and Rabbit, Tigger and Eeyore confront him, but then Pooh says he lost his bee tickler, and that he does not have Eeyore's tail or Rabbit's "Worm Wrangler", and Tigger then pretends he's looking for the most wanted tail.
As they search the woods, they pass Eeyore's tail but do not notice, but Piglet finds it it in his hands, deciding to use it as a protection against spookables.
After Tigger runs out of clues, Eeyore suggests they go to Piglet's, and they see him building a "Bully Bamboozler" out of a ballon and Eeyore's tail, and Piglet is caught (for "looking like Tigger's Wanted poster"), but then Pooh notices the "Bully Bamboozler", and Tigger bounces it and pops it, much to Piglet's dismay, only for Owl to take the tail after thinking it's a bell rope that belonged to his Uncle Torbett.
Owl uses it as a bell rope, which, Tigger places on Owl's footstool upon entering the house with his friends. Tigger then confronts Owl for stealing the gang's objects, only for Eeyore to let out a yell after his tail is reattached when he sits on it. Everyone then realizes that their respective objects are one and the same, and Eeyore states that it's his tail. Tigger then solves the case by saying that Eeyore's tail is the guilty party behind everything; it orchestrated its own disappearance (according to him) so that Eeyore would appreciate it more. Eeyore, humbled by the experience, decides to never take his tail for granted again and lets it walk in from for a change. However, Eeyore forget's that he is at Owl's and falls from the treehouse. Tigger then says that the case of Eeyore's "Tail tale" is officially closed, while Rabbit, saying he has lost his patience with Tigger's "Private Ear" nonsense, incurs Tigger to find it again, making Rabbit remark to himself if he will ever learn.