While Disney has made many Winnie the Pooh movies, this is only their second to be produced by Walt Disney Animation Studios. All of their other Winnie the Pooh movies, both those released direct to video/DVD and those released theatrically, were produced by DisneyToon Studios and thus are not considered to be official sequels.
This is only the third time that Walt Disney Animation Studios produced a sequel to one of their films from the Disney Animated Classics canon in-house. The previous instances are as follows: The Rescuers Down Under (1990) followed The Rescuers (1977) and Fantasia 2000 (1999) followed Fantasia (1940).
Kristen Anderson-Lopez and Robert Lopez not only wrote new songs for this movie but they also starred in this movie as the voice of Kanga (filling in for Kath Soucie) and the sounds of Pooh Bear's tummy respectively. Peter Del Vecho loved their songs so much that he rehired them 2 years later to write songs for the movie Frozen (2013).
In the past Winnie the Pooh movies Tigger was not named in the Winnie the Pooh theme song. But in this film however he is finally named in this song after Kanga and Roo.
The opening song features a slightly changed Hundred Acre Wood map, much like the original film. At the bottom of the map, it says, "Drawn by me" (implying Christopher Robin). On the second page, it says, "With help from Mr. Shepard." The original artist of the Winnie-the-Pooh books was E. H. Shepard.