Dotty trains Oso to go sail suit gliding. Oso couldn't find his sail suit because he forgot his backpack, so he uses his parachute instead. But he gets it caught on the ledge during his flight. That's when Oso receives a special alert. A boy named Evan is getting ready for his first day of kindergarten, but he's nervous because he's not sure if he can get ready all by himself. Can Oso help Evan get ready before it's time for school?