In 2009, Officer Cackowski briefly worked as a Greendale campus security as a side job to being a police officer. One night he caught three students (Annie Edison, Britta Perry and Shirley Bennett) breaking into Dean Pelton's office. Alongside his partner Foster he detained them until Pelton and the school's guidance counselor Gail arrived. As they dealt with the intruders he pointed out how uncomfortable Annie was. Months later at the school's Family Day function he was called to Greendale in his job as police officer. He had to deal with a fight that broke out between a student named Pierce Hawthorne and a teacher Ben Chang. Cackowski also questioned Jeff Winger and Hawthorne’s stepdaughter if they intended to hook up. He would return to the campus again in April the following year when a prank involving a cadaver occurred. He and his partner were met by Dean Pelton and mocked his concerns about the incident. At the crime scene he once again encountered students Annie Edison and Shirley Bennet. The bickering duo were at the time acting as volunteer campus security. Knowing that actually looking into the prank would be a waste of time for him and his partner he sarcastically turned over the investigation to them.
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").
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").
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").
The character who would later be officially identified as "Cackowski" (after the actor who portrayed him) was seen wearing several different name badges in his various appearances. His first appearance was in Season One as a security guard on campus which was explained in DVD commentaries as a side job to being a police offer. In this episode his badge clearly reads "Roger". In his second appearance his badge reads "Garcia" and third one his badge reads "Hirsh". It wasn't until the credits of the Season Two episode "Epidemiology" where he is officially named "Officer Cackowski".