The trio of University of Otago students were spotted on the roof of the five-storey Moran Building, which overlooks the Octagon, early on Sunday.
Police used a key to the building and arrested the men, who had shimmied between the Moran Building and a neighbouring building, to the second floor before accessing a fire escape.
Neighbourhood Policing team Sergeant Trevor Thompson said the climb was "absolutely perilous" and potentially deadly when climbing while intoxicated, in dark and wet conditions.
Tenants had complained to police about people unlawfully partying on their roof since the start of the year, a practice which the Otago Daily Times understands has been promoted via social networking sites.
Clothing, rubbish, beer and spirit bottles had been found on the roof and a lawyer's office had been broken into and beer stolen from a refrigerator.
Octagon Chambers barrister David More said a window was broken in that theft and a long blood trail was obvious. Skylights in the building had also been smashed when the party goers climbed higher above the lift shaft.
Earlier this year, he had chased three men from the roof, and it was a "worry that something more serious may happen".
"They are bloody fools and could really hurt themselves."
Mr More said there was less than a metre gap between the Moran Building and the neighbouring Terrace Bar, and "they must be reasonably fit and prepared to take a risk".
The men apprehended by police have been given diversion and referred to the University of Otago proctor. A further three are being sought in relation to the parties.
