After Tigger hears a bedtime story from Christopher Robin, he becomes the Masked Offender from the book and makes Piglet his sidekick. They go out to fight crime. But Tigger ends up causing trouble for his friends. First he beats up Rabbit's scarecrow because Tigger thinks that the scarecrow is a bad guy (which also making it safe for the crows to eat up Rabbit's garden), then Tigger fills up Gopher's hole because he believes that Gopher's house will be flooded from the rain if it's filled with holes, and then he chops down Owl's house because he believes that it's too high up (thinking the tree grew under it) and that if Owl sleep walks outside of his house he might fall to the ground and bend his beak.
Everyone in the Hundred Acre Wood is mad at the Masked Offender (except for Pooh and Piglet) and they all agree to teach him a lesson. They all create a monster out of glue and molasses named the Wacchamadingle, and lures Tigger to it. Piglet tries to stop Tigger, but it's too late. Tigger tries to fight the big goop, but ends up in a sticky situation. Their plan succeeds and Rabbit, Owl, and Gopher laugh at Tigger and hurt his feelings. Tigger, who feels defeated, hurt, and humiliated, pulls off his costume and also revealing himself to everyone much to their shock. Tigger then begins to walk back to Piglet's house with Piglet following behind vowing to never be the Masked Offender again. But when Rabbit, Owl, Pooh, and Gopher get stuck with the goop and is about to fall down to a pit, Piglet tries to get Tigger to go out and rescue them, but Tigger refuses since he is still upset about his humiliation. With no other choice, Piglet tries to help them himself, but gets stuck with the others. Tigger finally gives in and goes out to help them as the Masked Offender again, but he gets stuck with the others as well. The goop falls and is about to send everyone to their doom, but it bounces right up, due to that Tigger realizes that the goop can bounce. All of them eventually fall back to the ground, still stuck but okay.
The next day Tigger fixes Owl's house, but when he throws the hammer, it hits the tree which causes Owl's house to loosen and making it fall down again. Tigger mentions that it was easier being in his Masked Offender costume than fixing things up again but given the trouble he caused, he decides it's best to leave it in the closet for a while. Everyone except Tigger notices the house and begins to run away. He puts the suit back on, and says that you will never know when you need a call from the Masked Offender. When the tree is about to fall on him, the show turns into a book that shows part of a story that says The End, and the book closes.
This is one of few stories to not have been remastered on Disney+.
The scene where Owl and Pooh are inside Owl's house while the tree is falling is a homage to one of the original shorts, Winnie the Pooh and the Blustery Day.
