The Parole Board acknowledged Masters had a "number of" siblings involved in gangs and said the condition was "not intended to impede ordinary family contact".
A number of other conditions were set including not drinking or using drugs, attending assessments and treatment or counselling as directed by his probation officer and to comply with tenancy conditions at his address.
The special conditions were set to remain in place for six months past Masters' statutory release date - the official end of his sentence - on October 5.
The Herald can reveal that Masters is back before the courts after an alleged breach of those conditions.
He is charged with breaching a special condition "in that he associated with a known gang member".
Court documents do not state who that gang member was.
Masters has pleaded not guilty to the charge and will reappear in the Auckland District Court on January 21.
Masters during another court appearance relating to a covert police operation that netted more than 40 gang members. Photo / File
A Parole Board spokesman said as Masters' sentence end date had passed he could not be recalled to prison.
The Otara local rose to infamy in the early 2000s when he founded The Killer Beez - a street gang that made headlines and came to police attention after a number of unprovoked violent assaults.
He was formerly a vice-president of a chapter of the Tribesmen gang.
Back then Masters, now 40, was a competitive kickboxer and aspiring rapper who started his own record label - Colourway Records - in 2008.
In 2012 Masters publicly denied the Killer Beez were linked to any violence or methamphetamine dealing.
Several months later, following a covert police operation, he and 43 other people associated with the Killer Beez and Tribesmen gangs were arrested.
Police seized about $500,000 worth of P and cannabis, $20,000 cash, a large amount of stolen property, and motorcycles and cars under The Proceeds of Crime Act.
Masters was declined bail and spent four years in custody before finally pleading guilty to supplying methamphetamine, conspiracy to supply The Class-A drug, and laundering money through Colourway Records.
Masters founded the Killer Beez in the early 2000s. He was later jailed for 10 years, significantly diminishing the influence of the gang. Photo / Supplied
Over the years he has been declined parole a number of times.
But after appearing before the board in May it was decided he could be released.
Masters served his time at Auckland Prison at Paremoremo.
The Parole Board said Masters had a "high to moderate risk of re-offending" but was no longer considered an "undue risk" to the safety of the community.
According to the Parole Board, Masters has amassed some 40 convictions including a number for violence.
His most recent stint in prison was the seventh time he had been jailed for criminal offending.
The board said it was his longest term of imprisonment "by far".
In May he told the board that he intended to abide by his release conditions including any non-association orders.
He acknowledged that in the past he had held a "prominent position" within the Killer Beez.
"Mr Masters, at the hearing, indicated that he had no issue with any of the conditions that were proposed for him," said the board decision.
While the influence of the Killer Beez in the community was greatly diminished by the operation that saw Masters and his associates locked up - the gang continued to wreck havoc inside prisons.
Masters served his time at Auckland Prison at Paremoremo. Photo / File
One of the worst attacks was the fatal assault on prison guard Jason Palmer in 2010 in Spring Hill Prison.
Latu Kepu punched Palmer, who fell backwards and hit his head on the concrete. The Killer Bee was later convicted of manslaughter.
Members of the Killer Beez were also involved in the riot at the same Waikato prison in 2013, as well as attacks on prison guards at Auckland Prison in Paremoremo in 2016.
