An inmate who used an angle grinder to cut his way out of Paremoremo prison was moved there after guards at his previous jail found escape plans in his cell.
Kevin Polwart, 49, escaped on Wednesday afternoon by using the tool to cut through a steel fence around a concrete yard in which he was working.
Since his escape, more than 20 police staff, supported by dogs and a police helicopter, have been searching the Paremoremo area of Auckland's North Shore.
The Herald has learned prison staff raised concerns about the risk of Polwart escaping.
In 2001, he was on the run for 41 days after another escape.
Corrections Association president Beven Hanlon said the union had tried to stop Polwart being placed in a low-security wing.
But it felt it was ignored by management even though he had been identified as a risk.
A prison spokesman last night said management was not aware of any union concerns about Polwart.
Corrections Department national operations manager Robin Benefield said security concerns and prisoner employment programmes had to be balanced with the need to prepare inmates for eventual release.
"With any prisoner involved in employment, there is a risk involved. The department has a responsibility to prepare offenders for release."
The department said Polwart - who was 14 months from parole on a 16-year sentence - was using the angle grinder to work on concrete panels when he moved over to the fence and cut his way through.
The Herald also understands only two guards were supervising up to 60 inmates during the prison employment workshop, although four were supposed to be on duty.
Several hundred prisoners have gained qualifications and work experience through working in the yard, which has been operating for more than seven years.
Ms Benefield said Polwart had been working in the yard for more than eight months.
Wednesday's escape was similar to the June 2001 incident in which Polwart used wire cutters to break out of Rimutaka Prison near Upper Hutt.
During his 41 days on the run, he carried out an armed robbery of a security van in Auckland, stealing $60,000 in cash and cheques.
He was serving a 10-year sentence when he made his 2001 escape, and another six years were added to that after he was recaptured.
A report found that several departmental failures had eased Polwart's 2001 escape.
These included poor check of his cell on the morning of the jailbreak, limited electronic security systems, poor lighting and lax supervision.
His cell had not been searched in three months before the escape.
The Herald also understands Polwart was moved from Ngawha Prison in Northland to Paremoremo two years ago after staff found escape plans in his cell.
North Shore area commander Inspector Les Paterson said police wanted to send a message to Polwart.
"Hand yourself in before it goes too far ... Hand yourself in at the nearest police station. We'll put a couple of detectives in a car or fly them to wherever you are."
He said Polwart was from the Wellington area, but had been in prison for years so might have trouble re-establishing contacts.
Mr Patterson said anyone assisting him could face criminal charges.
Police would continue watching the Albany/Paremoremo area but could not be certain Polwart was nearby because of the amount of time that had passed since he escaped.
Low security for escaper despite record
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