Career criminal Anthony Sannd had previously escaped from prison but was classified only as a minimal risk when he decamped from a working party last month.
Despite his history and being denied parole in 2004, the 55-year-old was allowed out on the low-level security working party for the first time on February 1.
But while his fellow inmates collected firewood for the prison boiler, Sannd quietly slipped away from a distracted guard.
Sannd, who is also known as Ricardo Genovese, was recaptured on Monday night after 27 days on the run.
But, despite being back behind bars, questions are now being asked about why he was allowed into a position where he could escape in the first place.
The National Party's law and order spokesman, Simon Power, said the case was the latest in a large number of concerning incidents and reinforced calls for wide-ranging inquiry into the prison system.
Mr Power said one of the first principals of prisons was to ensure public safety. That had clearly failed in this case, he said.
Harry Hawthorn, regional manager for the Public Prisons Service Waikato/Central, said security and safety of the staff and public was a priority.
He said prisoners went through a rigorous series of checks - including behaviour records and security classifications - to determine if they were suitable for work parties.
Sannd was half way through a 13-year, nine-month sentence for the aggravated robberies of a bank, security van and Auckland City Art Gallery when he escaped from the working party last month.
It was the second time he had gone on the run while serving time for serious crimes.
In 1991, while getting close to the end of a 10-year aggravated robbery sentence, Sannd failed to return to prison after being allowed out on work parole.
That time he said he was in a motorbike accident which left him with no memory of the jail term he was serving.
This time he told police he had some unfinished business that he had to take care of.
It was not disclosed what that business was but during his days of freedom Sannd stole a $90,000 BMW and burgled the Onewhero home of a couple who allegedly "owed" him.
While stealing the car he wore a black wig which he was still wearing when he was arrested.
While on the loose police described Sannd as dangerous and warned the public not to approach him.
In October 1984 he helped steal nearly $300,000 from an Armourguard security van outside a supermarket in Birkenhead.
It was the biggest aggravated robbery to have ever occurred in New Zealand at the time and resulted in one of the largest court hearings the country had seen.
At that sentencing Justice Prichard said Sannd had previous convictions and was already serving another sentence for fraud.
He described Sannd as a menace to society and a hardened criminal who was resolved to live outside the law.
Several years later, during his sentencing for the theft of a $2 million James Tissot painting, Justice Potter said: "Unfortunately you have proved that nothing has changed."
Yesterday, Detective Senior Sergeant Neil Grimstone responded to claims that Sannd was also one of the most cunning criminals the country had ever seen by saying: "He's not that cunning because we managed to catch him."
Sannd pleaded guilty in the Pukekohe District Court to escaping custody, unlawfully taking the BMW and burglary.
He has been remanded in custody until later this month for sentencing.
Sannd's history
1984: Involved in what was then the country's biggest armed robbery of a security van outside an Auckland Supermarket.
1991: Escapes from Manawatu Prison while on work parole.
1992: Robs ANZ in Kerikeri of $69,000.
1998: Robs Armourguard van in Bombay, a Waiuku bank and the Auckland City Art Gallery - stealing a $2m Tissot painting.
Feb 2006: Escapes from Rangipo Prison by walking off during a work party. Steals BMW and burgles a house.
Hardened criminal's escape raises question over prison security
Anthony Sannd
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