In the hectic thirty minutes that start every day at Whitlock, Jack tries to retrieve his massage chair from Whitlock's intriguing payroll accountant, Lynette. Durbin and Helen prepare for the morning announcements. Michelle gives a eulogy.

Jack's war with his neighbor reaches a turning point when it threatens to ruin a date with Lynette. When the school photographer ups his rate, Durbin takes school pictures into his own hands.

When he's kicked off his Harvard phone plan, Jack is offered a chance to leapfrog onto Mary's on one condition: He helps her break up with her scuzzy boyfriend. Meanwhile, Anthony becomes Durbin's right-hand man.

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.

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

A tornado puts the school on lockdown. The kids write fan fiction about faculty members.

Jack attempts to get closer with the guys at work. Helen helps Principal Durbin grow a backbone.

Jack's students steal his Harvard pen. Principal Durbin fails the superintendent's inspection.