When Jack is disappointed with the popcorn maker he orders, he and the students plot revenge; Helen goes back to school to get her high school degree and chaos ensues in Principal Durbin's office in her absence.

Mr. Pugh plans a field trip for the Toledo chapter of the Ohio Naturalists; when Jack can't write his own book, he agrees to be ghostwrite for popular author Robin Shwank -- only to insert his own chapters into Shwank's book.

Jack accidentally loses a significant amount of money and it falls in the hands of the students; as Principal Durbin and Helen investigate who stole the money, the students and teachers admit to other wrongdoings.

Principle Durbin turns into a power-hungry maniac after self-publishing Jack's philosophy book.

Jack has Mary drive him to the doctor, but a prank results in him getting the same procedure twice; at school, Durbin and Helen embarrass themselves and the kids compete over class superlative titles.

As the school prepares for winter break, Jack tries to record a lecture as a way into the University of Wisconsin's philosophy department; frustrated and unable to finish the video, he falls asleep and has nightmares.

Helen has a vaping problem to overcome with the help of Durbin while Anthony's secret is revealed.

While the rest of the town prepares for the celebration of Toledo's annual Katie Holmes Day, Jack and Marissa plot to ruin the holiday pageant.