Eeyore has lost its tail, and Winnie the Pooh and his friends go looking for it. Each player has an Eeyore to which different tails can be attached. The game board is set up inside the box. Trees with various items which could be used for tails are inserted into holes in the board (without looking at which tree has which item). A card is flipped over, and all players now look for the tail that is depicted on that card. They do that by rolling and moving along the trees; at the end of their move, they pull out the tree and check if it is the right one. When finding Owl, the active player may secretly switch two trees; finding other characters from the book cause other effects. When all tails are found, players have to find Owl who has the original tail which is worth two other tails. The player with most tails collected is the winner.