Deep in the Hundred Acre Wood, a young Christopher Robin (Orton O'Brien) goes on many adventures with his friends. They explore new places, and he helps set up traps for Heffalumps and Woozles. However, soon comes the day that Christopher must say goodbye, as he is preparing to leave for boarding school.
Christopher's friends - Winnie The Pooh, Tigger (both voiced by Jim Cummings), Piglet (Nick Mohamed), Eeyore (Brad Garrett), Rabbit (Peter Capaldi), Owl (Toby Jones), Kanga (Sophie Okonedo), and Roo (Sara Sheen) - have prepared a farewell party for him, and he brings a cake to celebrate. After the others pass out from a sugar rush, Christopher and Pooh go by their favorite spot, a log next to a tree that has a great view of the sunset. Christopher promises not to forget Pooh when he goes away.
Christopher's parents send him off to boarding school. Soon after, Christopher's father dies. As he gets older (now played by Ewan McGregor), he meets an architect named Evelyn (Hayley Atwell), whom he later marries before he must fight in World War II, causing him to miss the birth of their child. All these years, Pooh remains waiting by the door on the tree in case Christopher should return. Upon his return home, Christopher meets his daughter, Madeline (Bronte Carmichael). He gets a job working for Winslow Enterprises, a company that manufactures and distributes luggage. Christopher becomes so consumed by his work and desire to provide for his family that he has lost his sense of fun.
At work, Christopher reviews a number of changes made by his employees to cut back costs. He is called in to meet with his boss, Giles Winslow (Mark Gatiss). He wants to cut back costs by 20%, which means he wants Christopher to pick who should be fired. Giles orders Christopher to have the paperwork ready by Monday. The extra work puts a damper on a planned trip to Sussex with Evelyn and Madeline. Christopher tries to explain the situation to them. Madeline is disappointed, but she is used to her father making more time for work than for her. Evelyn is more upset, reminding her husband that his life is passing him by while he drowns himself in work. She also tells him that Evelyn is close to turning out like him, since Christopher is planning to send her off to a prestigious boarding school, and so he makes her catch up on studies.
Back in the Hundred Acre Wood, Pooh wakes up and finds that he has no honey. He goes outside his home and tries to find his friends, but none of them seem to be around. He becomes worried and then sees the door on the tree where he always waited for Christopher to come back, and Pooh steps through it himself.
Evelyn and Madeline head off to the cottage while Christopher stays behind to work. He takes a break and sits outside to clear his head when he discovers Pooh sitting behind him. Christopher is surprised that Pooh made it to London. Pooh explains that he can't find his friends, fearing they have been taken by a Heffalump, and he was hoping that Christopher may help, but the door on the tree is no longer there. He takes Pooh into his house for the time being and gives him honey as a snack. Soon, Pooh starts to cause some trouble by leaving sticky footprints on the carpet and breaking a shelf in the kitchen, which leads to other shelves and the items on them to break as well. Christopher decides to take Pooh to Sussex to find the tree.
Christopher and Pooh board the train going to Sussex, with Christopher trying to remind Pooh not to draw attention to them since he is a talking teddy bear. They get to Sussex and find the tree, and both of them go inside to the Hundred Acre Wood. They head off to find Pooh's friends, but they end up walking in a circle because Pooh can't guide them properly. To make things worse, Christopher's paperwork falls out of his briefcase and start flying all around. Christopher starts to get frustrated with Pooh acting childishly, and they get separated as a fog sets in the woods. Christopher tries to find Pooh, but ends up falling in a trap for Heffalumps, and he gets knocked unconscious, just as it starts raining. He has a nightmare in which he and Pooh are underwater, and a Heffalump snatches Christopher with its trunk.
Christopher wakes up and climbs out of the hole. He walks until he finds Eeyore floating along the river, about to go over a small waterfall. Eeyore doesn't recognize Christopher, but he carries Eeyore with him until they find the others. Christopher follows a trail of acorns to find Piglet hiding behind a tree, fearing that there are Heffalumps around and that Christopher is one of them. Christopher then finds the rest of the animals hiding in a log, and they also believe him to be a Heffalump. He tries to explain that what they heard was the weather vane from Owl's house making a noise that scared them. To prove he's really Christopher Robin, he goes out and pretends to fight a Heffalump and win, leading the others to come out and realize it's really him. They then go to find Pooh sitting on the log, and Christopher reconciles with his old friend.
The next morning, Christopher finds that he overslept and is about to miss his presentation. He leaves the Hundred Acre Wood and tries to sneak out, but he is spotted by Madeline and Evelyn, and he must make an excuse to return home. Madeline becomes upset, and Evelyn tells her to take a break from her studies and to go outside and play.
Pooh finds that Tigger took out Christopher's paperwork to dry since it got wet, and thinks that a Woozle (Winslow) will eat him if he doesn't have it. Pooh, Tigger, Piglet, and Eeyore all go through the door into London and meet Madeline, who is at first freaked out but then recognizes Pooh from old drawings she found from her father, and he knows her from what Christopher mentioned about his family. Pooh tells Madeline that they need to give Christopher his papers, so she takes them on her bike back to London after leaving a note for her mother. Evelyn finds the note and drives off to find her.
Madeline boards the train back with her new animal friends, while Christopher is headed to work. Madeline takes a cab ride, but the cabbie gets spooked when he sees Tigger talking, and he crashes into a newspaper stand. Madeline spots a van headed for Winslow Enterprises, and she hops in the back with the others stowing away in some luggage. Evelyn then arrives in London and goes to find Christopher just as he is already meeting with Giles and his father, Old Man Winslow (Oliver Ford Davies). He steps out with Evelyn to go find Madeline. The luggage from the truck falls out, sending Tigger, Piglet, and Eeyore flying onto their car. They catch up with Madeline, who is with Pooh. Christopher sits to talk to Evelyn and says her happiness is important to him and that she doesn't have to go to the boarding school if she doesn't want to. Pooh returns Christopher his papers, and Evelyn makes a comment about seeing things from a different perpsective, which gives Christopher an idea for his presentation.
Christopher returns to work and sees that Giles has already started letting the efficiency department go. He goes up to make his pitch to Winslow Sr, stating that if they allow their employees to take paid vacations, they may have more reason to purchase their luggages, and if they sell them at cheaper prices, more people will be persuaded to buy them. Winslow Sr likes the idea, but Giles starts to make an argument until his father asks what he did for his part in the presentation. Giles tries to cover himself, but his father sees that he has spent more time golfing over the weekend. Winslow Sr accepts Christopher's idea and lets him take a vacation with his family. Before leaving, Giles thinks Eeyore was staring at him, but his father thinks he's crazy.
Christopher brings Evelyn and Madeline into the Hundred Acre Wood where they meet the rest of the animals. As they have tea, Christopher and Pooh sit by the tree to watch the sunset. Pooh asks what day it is, and Christopher says "Today", to which Pooh responds, "My favorite day." Christopher tells him, "Silly old bear."
During the credits, the Winslow employees can be seen enjoying themselves on the beach while Richard Sherman plays the piano. We then see Pooh and his friends sitting by the sand as well.
*CUT TO THE CHASE*
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Young Christopher Robin must leave behind his friends in the Hundred Acre Wood when he is set to go to boarding school. Although he promises Winnie The Pooh that he won't forget him, Christopher experiences the weight of growing up through the death of his father, as well as fighting in World War II. As an adult, he marries a woman named Evelyn, and they have a daughter named Madeline, but Christopher becomes so consumed by his work at Winslow Enterprises that he frequently neglects his family and loses his sense of fun. What's worse is that his boss, Giles Winslow, wants him to lay off his employees to cut back company costs.
Pooh wakes up one day to find that his friends have gone missing, so he enters through the tree into London to find Christopher. While surprised at first, Christopher takes Pooh back to the Hundred Acre Wood to find their friends, but Christopher snaps at Pooh for his childish behavior. Later, he finds Eeyore, Piglet, Tigger, Owl, Rabbit, Kanga, and Roo all hiding because they think a Heffalump is around. Christopher reaches to find his fun self and pretends to fight a Heffalump to get his friends to see it's really him. They find Pooh and reunite, but Christopher must leave to get back to work. Unfortunately, he's left behind some important paperwork, so Pooh goes with Tigger, Piglet, and Eeyore to return it to him because they think a Woozle (Winslow) will eat him. They meet Madeline and join her as they head back to London.
After finding Evelyn, Madeline, and the animals, Christopher tells his daughter that her happiness is important to him, and that she should enjoy her childhood while she can. He returns to the company for his presentation, and he manages to convince Old Man Winslow (Giles's father) that they can increase sales by letting the employees take paid vacations so they can buy luggages from their company. Winslow Sr likes the idea and lets Christopher take a vacation with his family.
Christopher takes Evelyn and Madeline to the Hundred Acre Wood for the first time, and he enjoys the sunset with Pooh.
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