Jack decides to use his students to enact revenge on his rival; Principal Durbin struggles to control Jack.

Jack leaves his class unattended and lands himself in “teacher jail” after one of his students suffers a minor injury. Initially, Jack enjoys the paid time off, but the situation takes a turn when the resulting investigation targets Durbin. Meanwhile, Helen acts as the substitute teacher in Jack’s absence, much to the students’ dismay.

When the local bookstore chooses Miles’ new book as their “staff pick,” Jack instructs his students to get jobs at the store in order to change the pick from the inside. Meanwhile, Principal Durbin struggles to assert his authority while attempting to make budget cuts.

Jack (Glenn Howerton) gets into a petty dispute with Marcus (Nick Peine), the President of Student Council. Marcus surprisingly refuses to back down and the situation escalates much too far. Stef (Lyric Lewis) sells makeup at school as a side business.

Jack tries to pick up dates in Toledo with the help of Stef, Mary and Michelle. Meanwhile, Principal Durbin grows jealous of his assistant, Helen, after her comedic rendition of the daily announcements proves to be a big hit with the students and the faculty.

When Jack (Glenn Howerton) is attracted to a student's mother (guest star Erinn Hayes) at a parent-teacher conference, he feigns interest in her son, Colin (Tucker Albrizzi). A group of parents complain to Principal Durbin (Patton Oswalt) when they notice a piece of controversial student art from Mary's (Mary Sohn) class.