In the study group's first year at school, Cackowski was moonlighting as a security guard at Greendale. One night he caught Annie, Shirley and Britta who were trying to break into Dean Pelton's office to get a good look at an anatomically correct mannequin that was in there for the STD Fair. He held them there for interrogation by Dean and Gail the student counselor. Gail hoped to diffuse the awkwardness of the situation by having everyone say the word "penis". Cackowski quickly pointed out that Annie didn't say it and she refused stating she was comfortable being a prude. After she finished her speech, Cackowski didn't bother trying to stop her when she marched out of the office ("The Politics of Human Sexuality").
Cackowski pointing at Annie for not saying "penis".
On Greendale's Family Day event he was called in to deal with the aftermath of a physical altercation between Ben Chang and Pierce Hawthorne over a simple misunderstanding of a Pictionary clue. Once the interviews were over, Pierce's Pictionary partners Jeff and his former step daughter Amber claimed they were going to get some coffee. Pierce questioned if "coffee" was a code word for sex which they vehemently denied. A skeptical Cackowski then chimed in and asked if that was truly the case ("Basic Genealogy").
Is "coffee" code for sex?
He was next seen on campus in his actual job as a police officer alongside his partner Officer Hancock. They were investigating what appeared to be a bizarre April Fool's joke on campus involving a cadaver being flung from the second story of the science lab. Hancock and Cackowski assured Dean Pelton that the incident wouldn't affect the school's reputation which was already bad. They were interrupted by the arrival of a campus patrol cart that was driven by volunteer student security guards Annie Edison and Shirley Bennett. They marched up to the two officers and after introducing themselves tried to claim jurisdiction. Amused by their antics, Cackowski and his partner allowed them to take over the investigation since it was only a misdemeanor crime ("The Science of Illusion").
Now on the study group committee's sixth year, Cackowski is called to investigate the leaking of the Greendale's staff e-mails, alongside his partner Warburton. He finds a message by the hackers demanding a show the school booked to be cancelled, and eventually discovers the culprit, Ryan (aka "StringCheeseHustler" or "CaptainTitty"). He also seems disappointed by the remaining founding members of the committee holding him at arm's length despite having known him for five years ("Basic Email Security"). Later, he returns to Greendale, off duty (as he takes macrame at Greendale after work), when the committee grifts the grifting professor Roger DeSalvo, and reveals the reason he became a cop is his mentally challenged cousin ("You know, lot of bullies out there") ("Grifting 101").