In post-World War II London, Christopher Robin, now a grown man with a family and a demanding job, has lost touch with his sense of imagination and the joyful exuberance of his childhood. Tasked with finding cost-saving measures at the luggage company he works for, which could result in layoffs for his colleagues, Christopher is consumed by the pressures of adulthood, leaving little time for his wife, Evelyn, and daughter, Madeline. The fun and carefree days spent in the Hundred Acre Wood with his whimsical childhood friends seem a distant memory, replaced by the monotonous routine of work and responsibility.

Unbeknownst to Christopher, deep in the Hundred Acre Wood, his old friend Winnie the Pooh finds himself unable to locate his companions—Piglet, Eeyore, and Tigger among others—and decides to seek out Christopher Robin for help. Emergence into the bustling streets of London bewilders Pooh, but his unwavering faith in his friend leads him to a surprising and emotional reunion with Christopher. The encounter serves as an awakening for Christopher, who is torn between the demands of his job and the rediscovered joy and simplicity of his past. The arrival of Pooh brings both warmth and chaos to Christopher's carefully structured life, prompting him to reevaluate his priorities and recall the importance of friendship and family.