Mimi Alexander (Madeline Malone) and Kayla Joy (Olive Greene) are cousins in real life. During many of their scenes together, Kayla struggled to keep a straight face, and she can be seen giggling. Additionally, Kayla Joy and Mackenna Eagan (Penelope Davis) are sisters in real life, though they shared no scenes.
The classroom used as Mr. Thomas's (James Clark) classroom was actually the Journalism classroom used by Kayla Joy while she worked on the school newspaper in high school.
The title is a play on words, as the character Mr. Dean was named after the real school principal at the school where filming took place.
James Clark (Mr. Thomas) improvised many of his lines.
To prepare for filming, Jennifer Eagan had the actors playing the students actually write essays about why their characters were in detention. In true character form, Nicole Moriarty and Mimi Alexander were the only two to finish theirs. Nicole's essay was approximately 3 pages long, front and back. Logan Shaw claimed to have never recieved the email with the instructions. Kayla Joy and Luke B. Carlson never wrote essays. Instead, Kayla is seen writing the lyrics to "All Star" by Smash Mouth, and Luke's character Henry focuses on a mildly obscene drawing during the essay sequence.