Teina Pora, convicted of the rape and murder of Susan Burdett in 1992, will appear before the Parole Board for the 12th time on Monday.
Pora was sentenced to life imprisonment in 1994 for the crimes committed during the burglary of Ms Burdett's Papatoetoe home.
He has maintained his innocence since he was charged and is seeking an appeal to the Privy Council.
The appearance comes after calls for a review of his case from politicians and the Police Association.
"He's as hopeful as he can be [of being granted parole] but he is mindful of what has happened in the past," private investigator Tim McKinnel told the Weekend Herald .
Mr McKinnel said Pora had addressed the issues raised by the Parole Board when he was last considered for release six months ago. He had been released to work as a painter every day of the working week for the past few months. "He's done everything he possibly can," McKinnel said. "He's got his fingers crossed."
Pora was 17 when he was charged and is in his 21st year in prison. He was found guilty at a retrial in 2000 and those convictions were upheld by the Court of Appeal.
His application for appeal to the Privy Council is based on new expert evidence on false confessions and criminal profiling that concludes serial rapist Malcolm Rewa, whose semen was found at the scene, was the sole offender.
Rewa was convicted of attacks on 25 women, including the rape of Ms Burdett, but two juries could not decide if he was guilty of her murder. In the other 24 cases Rewa acted alone.
In the hope of gaining a $20,000 reward, Pora is said to have made up his confession of aiding Mongrel Mob members. The gang members named were cleared by DNA. Rewa was a senior member of a gang that was at war with the Mongrel Mob.
Pora has been eligible for parole since December 2003 and was last considered for release in April. In denying him parole then, the board noted an incident in January where a lighter, screwdriver and "an objectionable item" were found in his cell.
This was troubling as it showed an inability to abide by prison rules and was set against the "considerable progress" Pora had made, the board said.
He needed longer home releases, to show he could manage in the community, and a "detailed" release plan. The board ordered he be seen again in six months rather than the usual year.