Justice David Gendall was sentencing a key player and another man described as a ''foot soldier'' in what he called a ''sophisticated and well-organised growing and selling ring''.
Brian Anthony McCarthy (63), a guide, of Queenstown, and Brodie Raymond Anderson (25), unemployed dairy herd manager, of Mossburn, were jailed for their part in the ring.
They were two of five men arrested in May last year after a three-and-a-half-year police investigation called Operation Canary.
McCarthy, who earlier pleaded guilty to 10 charges of cultivating cannabis, three of possessing cannabis for supply, two of selling cannabis and one of conspiring to sell cannabis, was sentenced to four years and three months in prison.
Anderson received a two-year sentence after earlier admitting 15 charges of offering to sell cannabis, seven of possessing cannabis for supply and three of cultivation.
McCarthy was a major participant in the ring, which was broken when police made their arrests, Justice Gendall said. He set up and tended 10 cannabis plots, helped with the harvesting - assisted by armed men wearing balaclava disguises - and sold cannabis in bulk.
The total number of cannabis plants grown during the time police were following the ring was unknown, he said, but 361 plants were found in seven plots.
During one monitored sale, McCarthy sold 5.8kg of cannabis, while 4.5kg was sold on another occasion. When his Kelvin Heights home was searched, 24kg of premium cannabis was found.
Appearing for McCarthy, John Westgate, of Dunedin, said McCarthy had been ''seduced by the lifestyle of selling cannabis'' and would ''regret it forever''.
He read a note written by McCarthy in which the defendant said since his arrest he had had time to think about the harm the cannabis he had sold had caused to smokers of all ages. He was ''very remorseful''.
McCarthy had lost a huge amount personally because of his offending, including having $111,000 in a trust account and his $580,000 home seized by the Crown, Mr Westgate said.
He had pleaded guilty at an early opportunity and had co-operated with police.
Justice Gendall said while McCarthy was entitled to a discount for his guilty plea, his remorse, his co-operation, and because he was a first offender, a prison sentence was required that was a deterrent, but not crushing.
Appearing for Anderson, Sonia Vidal, of Queenstown, said it was accepted he was a ''foot soldier'' in the cannabis ring, ''whereas McCarthy was at the top''.
Anderson told police last year he had agreed to sell drugs because he was in debt and selling seemed an easy way out.
Justice Gendall said monitoring of Anderson's cellphone showed he offered to sell cannabis 42 times between June 2011 and April last year.
He also helped to harvest 62 plants during the 2010-11 growing year, and when his home was searched on April 17 last year a large amount of cannabis was found spread out to dry in a bedroom, plus 57gm of cannabis in sellable form.
Anderson had a good work record and a limited criminal history, with no previous drug convictions, Justice Gendall said, but the sentence had to reflect the length and extent of his involvement with the ring.
He granted Anderson leave to apply for home detention in the future.
In September, Frank Mathew Tainton (61) was sentenced to two years and nine months' jail for his part in the ring, and an order made for forfeiture of his vehicle.
A 43-year-old Invercargill man has pleaded not guilty to 12 charges. A charge against a fifth man was withdrawn.
The Numbers
• 10 cannabis plots
• 361 plants found in seven plots
