Winnie the Pooh skips through the Hundred Acre Wood singing the title song "Too Smart for Strangers". He then asks himself what exactly is a stranger. He soon meets up with Piglet and then remembers that a stranger is somebody you don't know. Pooh and Piglet discuss about how you can tell if someone is a stranger, with Pooh advising Piglet that all strangers cannot be trusted. Piglet becomes afraid and Pooh invites him into his house where it's safe and they sing about what to do to help yourself in the face of a stranger.
The show then goes to Tigger and Roo, where they talk about where strangers can be found and what to do when you encounter one. Tigger says that you should run away as fast as you can and do anything you can to get away, and that you shoudn't be afraid to tell somebody you trust. As Tigger drops Roo off at his mother's house and goes along his merry way, he hears bushes rattling and fears a stranger is about, but is relieves to find it's only Eeyore. Rabbit then magically appears and tells Tigger and Eeyore about tricks that strangers sometimes pull to lure kids, like offering candy or money.
Pooh and Piglet then let Owl take over the show. Owl teaches the audience about what to do if you're home alone and a stranger arrives at the door or calls you on the phone. Once again, Rabbit appears to talk about tricks that strangers pull, such as saying if he's a friend of a parent. Owl advises the audience to say no and not to answer no matter what they say. Tigger also stops by to tell the viewer to always keep the door locked when you're home alone.
The show goes back to Pooh and Piglet. Piglet reminds Pooh that sometimes, trouble doesn't always come from strangers, but from people you know. Pooh then tells Piglet about certain private places on his body what nobody but himself is allowed to touch. Pooh then goes on to tell the difference between "okay" and "not okay" touching and sings a song about saying "no" to people who touch him in what he feels is "not okay". Rabbit then appears to Pooh and Piglet and reminds them about threats strangers can make to get children wouldn't tell, telling the audience not to believe them and tell someone they trust anyway. Pooh and Piglet then discuss all that we've learned and tell the viewer if they follow all those rules, they'll be too smart for strangers. The show ends with Pooh and all of his friends having a celebration and saying goodbye.
- "Too Smart for Strangers"
- "Three Things to Remember"
- "Keep Telling Them Till They Do"
- "Don't Be Fooled by Tricks"
- "When You're Home Alone"
- "Say No"
- "Keep Telling Them Till They Do" (reprise)
- "Three Things to Remember" (reprise)
- "Too Smart for Strangers" (reprise)
- Hal Smith as WInnie the Pooh and Owl
- Phil Baron as Piglet
- Will Ryan and Tigger and Rabbit
- Ron Gans as Eeyore
- Kim Christianson as Roo
- In recent years, especially on the Internet, this special became notorious for the scene where Pooh and Piglet discuss what to do if either a stranger or someone you know "touches you in a not okay way".
- The special was also infamous for implying that only strangers try to do abductions on children and that you are safe at a neighbor's house, with several people, including Brad Jones of the web riff series DVD-R Hell pointing out that a lot of abductions are done by people the abductees know full well instead of strangers such as neighbors, teachers or relatives.