One day, Pooh comes across his friend Eeyore, the gloomy, gray donkey, looking glum. Pooh learns that Eeyore is sad because his tail has disappeared, and Pooh resolves to help find it. Pooh visits their friend Owl, because “if anyone knows anything about anything, [...] it’s Owl who knows something about something” (48).

Owl uses increasingly large words to explain that they should offer a reward to whoever finds Eeyore’s tail, and Pooh listens less and less, instead daydreaming about honey. Finally, Owl shows off the signs on his door as examples of why Christopher Robin should write the reward notice, and Pooh realizes that Owl’s bell-pull rope is Eeyore’s tail. Pooh takes it to Eeyore, who is happy to have it back.

One day, Christopher Robin tells Pooh and Piglet that he saw a Heffalump (an elephant-like creature), and Pooh decides to catch one of the creatures. After some thinking about how best to do this, Pooh and Piglet dig a deep pit and put a jar of honey at the bottom to tempt the Heffalump, who they reason will fall in because it will be looking up at the sky and not notice the giant hole in the ground.