Christopher Robin

After his living toy friends from the Hundred Acre Wood throw him a farewell party before he departs for boarding school, Christopher Robin reassures Winnie the Pooh that he will never forget him. Nevertheless, his rough experiences at school and his father's death force his maturation, and he soon forgets his Hundred Acre Wood friends. He later marries architect Evelyn, has a daughter named Madeline, serves in the British Army during World War II, and gets a job as Director of Efficiency at Winslow Luggages in London, unintentionally neglecting his family. Christopher's superior, Giles Winslow Jr., tells him to decrease expenditures by 20%, largely by choosing which employees to lay off, and to present his plan on Monday. Christopher misses joining his family at their countryside cottage in Sussex for a summer-ending weekend.
The next morning, Pooh wakes up to find his friends are missing. Looking for them, he enters a door that Christopher normally came out of, and finds himself in London. He reunites with Christopher, who is shocked to see Pooh but takes him home, before bringing him back to Sussex on the train the following day. Passing by the cottage, they enter the Hundred Acre Wood. Pooh, attempting to return Christopher's compass, trips into Christopher's briefcase, spilling his papers. Christopher angrily reminds Pooh that he is now an adult, before they are separated in the fog. Christopher falls into a Heffalump trap, which is flooded by rainfall.
Christopher discovers Eeyore and Piglet, who lead him to the others, hiding in a log from what they believe to be a Heffalump but is the squeaking of a rusty, fallen weather vane from Owl's house. He pretends to defeat the Heffalump, proving his identity. When they reunite with Pooh, Christopher apologizes for his earlier outburst and explains his dilemma. Pooh forgives and embraces him. The next day, Christopher hurries out of the Hundred Acre Wood to make his presentation after Tigger gives him his briefcase.
After Pooh discovers that Tigger removed Christopher's paperwork when drying his briefcase, Pooh, Tigger, Piglet and Eeyore decide to travel to London to return it. Madeline, wanting to dissuade her father about sending her to boarding school, recognizes them from Christopher's drawings and joins them. Evelyn discovers a note Madeline wrote, and invites Christopher to search for their daughter just as he discovers gifts that Tigger left him. Madeline's group stows away in crates, but Tigger, Eeyore and Piglet are accidentally ejected, and encounter her parents. Pooh and Madeline arrive near the Winslow building, and reunite with Christopher and the others, but Madeline trips on some steps and loses all but one of the papers. Christopher assures Madeline that she is too important to him to be sent away.
Using the paper Madeline saved, Christopher improvises a new plan involving selling luggage at reduced prices to ordinary people to increase demand, and giving employees paid leave. Winslow Jr. dismisses the idea, but his father Giles Winslow Sr. warmly agrees to it. Christopher further humiliates Winslow Jr., who contributed nothing to the plan, instead playing golf all weekend. Christopher finally takes his family into the Hundred Acre Wood to meet his friends for a picnic.