Robin (Ewan McGregor) was once an innocent little boy with many strange friends, but now he has grown up and works in a suitcase company. In addition to racking his brains to complete the tasks assigned by his boss, he also has to find ways to squeeze out time to accompany his wife Evelyn (Hayley Atwell) and daughter Madeline (Bronte Carmichael). Robin loves his family very much, but such a life inevitably makes him feel a little suffocated. One day, Robin's childhood playmate Winnie the Pooh (voiced by Jim Cummings) suddenly appeared in front of him again and asked him to do him a favor. Obviously, Winnie still regards Robin as the simple boy before, which makes Robin feel a little at a loss.