On a dare from Louie, Shere Khan sets out to prove his courage by roaring from the top of Pinnacle Rock in the Wasteland, unaware that the fierce baboon Mahra and her sons have returned to their Pinnacle Rock cave.

Anxious to prove himself equal to Shere Khan, Bagheera enters a number of "contests" with the tiger... culminating with his losing his voice, and his pride. Bagheera finds a discarded pocket watch. Although he doesn't know what it is, he's convinced this "man thing" must have magical powers, despite Shere Khan's warnings to the contrary.

A lost female elephant happens into the Lair, and the boys discover that even "a girl" has what it takes to survive in the jungle. Buzzards Arthur and Cecil, hoping to dine on a seemingly decrepit old water buffalo, try to trick Shere Khan into putting the buffalo out of his misery (since the birds can't eat anything that's still alive).

Kaa encounters a young mongoose in the jungle and brings him back to the cubs' Lair, unaware that snakes and mongooses are among the deadliest enemies in the jungle. Hathi decides the cubs must get in shape to prepare for the coming monsoon season - especially Baloo, who resists the others' every attempt to make him change his lazy ways.

A misunderstanding between Louie and the other cubs sends Louie packing...but only when he ends up enslaved by the baboons do Louie and his friends realize how much they miss one another.

When a pack of rampaging wild dogs enter the jungle, the cubs are forced to work together as a team to run off the marauders.