This episode contains examples of the following tropes:
Abnormal Ammo: During the pirate fantasy sequence, Christopher Robin, Pooh, and Piglet fire pillows from a cannon at Tigger's ship.
An Aesop: Babysitting may be more trouble than what you think.
Babysitting Episode: In the first half of the episode, an unnamed babysitter takes care of Christopher Robin. In the latter half, Christopher Robin has to babysit Roo while Kanga goes out into the Hundred Acre Wood.
Break the Cutie: Kanga breaks down crying after failing to find Roo.
Does This Remind You of Anything?: Kanga breaks down crying over Roo going missing. But due to Roo being babysat by Tigger at the time of going missing, the double meaning hidden here is a metaphorical allegory to child abduction.
The Faceless: As with Christopher Robin's mother, the audience never sees the babysitter's face.
Fake-Out Opening: The opening scene where Christopher Robin rescues his friends from prison via train is actually his imagination.
Halfway Plot Switch: The first half of the episode involves Christopher Robin causing trouble for his babysitter while refusing to go to sleep. In the second half, Christopher Robin gets to exprience the babysitting himself.
Just Train Wrong: During the Fake-Out Opening when the train goes down a steep hill, Tigger has Piglet hit the brakes; the control he activates is the roof rope, which is what blows the whistle.
Loophole Abuse: As put by Tigger, the babysitter said "get into bed," but she didn't say "go to sleep."
