In the film, which is narrated by John Cleese, the aforementioned residents of the Hundred Acre Wood embark on a quest to save Christopher Robin from an imaginary culprit while Pooh deals with a hunger for honey.

Pooh, Owl, and Christopher Robin organize a contest for anyone who can find a replacement tail for Eeyore, but every attempt fails, and no one wins the prize (a pot of honey).

In response, Rabbit comes up with a plan to stop the creature by leaving a trail of items leading to a pit in order to trap him.

While struggling to follow through with Rabbit's plan, Pooh falls into the Backson pit after finding an empty honey pot above it.

Piglet heads towards Christopher Robin's house to find a rope to rescue everyone, but he gets frightened off after spotting Tigger in his Backson costume.

As a reward for this act of selflessness, everyone in the Hundred Acre Wood presents Pooh with a giant honey pot, much to his delight.

In a post-credits scene, a real Backson, who is revealed to be a very nice and gentle creature, discovers the trail of items that Pooh and his friends left and ends up falling into their pit.

Walt Disney Animation Studios' chief creative officer John Lasseter first approached Stephen Anderson and Don Hall in November 2008 about making a new Winnie the Pooh film for theaters, with the two becoming enthusiastic at the idea and accepting the project.

[9][10] In 2009, Lasseter, Anderson and Hall viewed the classic Winnie the Pooh feature shorts and films to figure out how to make the title character culturally relevant.

A. Milne's original stories, the filmmakers enlisted Burny Mattinson, a Disney veteran who worked as the key animator on the 1974 short Winnie the Pooh and Tigger Too, to serve as lead storyboard artist for the film, with Anderson and Hall directing.

Mattinson's five-minute pitch for the sequence where Eeyore loses his tail is credited with convincing Disney executives to make the film a feature-length work instead of a featurette.

[9] Regarding the decision to use hand-drawn (traditional) animation in lieu of computer-generated imagery (CGI), Anderson stated that "If this were a fully CG-animated [sic] and rendered and lit Pooh, it just wouldn’t feel right.

The production would also use the same software utilized for Princess and the Frog, Toon Boom Animation's Harmony, to digitally ink and paint the drawings.

The website's consensus reads: "Short, nostalgic, and gently whimsical, Winnie the Pooh offers young audiences—and their parents—a sweetly traditional family treat.

[27] Gary Goldstein of the Los Angeles Times says the film "proves a fitting tribute to one of the last century's most enduring children's tales.

[29] Roger Ebert, giving it 3 stars out of 4, wrote in his review, "In a time of shock-value 3-D animation and special effects, the look of the film is gentle and pleasing.