In this compilation, Pooh, Piglet and Tigger literally pop out for the surprise of the Book of Pooh into the live-action tour of Christopher Robin's bedroom for a surprise, but they didn't find Christopher there. Tigger decides to search for Christopher's journal, in hopes of finding out where he's gone, but accidentally ends up by making a real mess. While they're trying to clean up the bedroom, Piglet notices that Christopher Robin had marked some chapters of the Book of Pooh with special bookmarks, featuring each of his friends as preschoolers' hosts. As the story continues, Rabbit, Kessie and Eeyore each show up too. One by one, the characters ask Mr. Narrator to read the book's stories for them, leading to the following episodes:
- Over the Hill (Winnie the Pooh)
- Tigger’s Replacement (Piglet)
- Kessie Wises Up (Kessie)
- Greenhorn with a Green Thumb (Rabbit)
- Night of the Waking Tigger (Tigger)
- Eeyore’s Tailiversary (Eeyore)
At the end, Pooh and his friends clean up the accidental mess they've made. Christopher Robin gets in and says that a journal is something you write about things that happen in, but only after they've happened.