He was earlier recalled to prison four times, dating as far back as 2008.
In a decision released today, the Parole Board said that his release plan lacked specificity and that the Board should look into residential restrictions such as an electronically verifiable curfew.
"Mr Wickcliffe has previously been released to Maketu with, it was suggested, extensive support from family and other organisations but that has not worked for him because he has returned to prison," the Board said.
The prisoner had regularly seen a psychologist and counsellor about his recidivist behaviour and told a prison psychologist that his "unhelpful" view of the world has resulted in regular stints back in prison.
He identified problems involving isolation and the difficult associates who played a part in dragging him back into criminal behaviour while out of prison.
"All of those factors illustrate that we are satisfied he remains an undue risk without an adequate release plan," the board said.
Wickcliffe has reportedly behaved well in prison and was to possibly be on the release-to-work programme, although his age may mean he is ineligible for this.
He will be up for parole again in six months and the board said it expected to see a "far more detailed plan" about what Wickcliffe's life outside prison would look like.
This would include the type of support that would be provided for him in the community, confirmation that he will receive further drug and alcohol treatment and residential restrictions.
Wickliffe is the only prisoner to have escaped Auckland Prison Paremoremo twice and has spent more time in prison than any other Kiwi, except one.