One of two men who escaped from a Vancouver Island prison and remained on the lam for two days in July was supposed to be sentenced for the escape Monday.

But the judge halted the proceedings to figure out why the 30-year-old violent offender with a lengthy history of escaping from incarceration was being housed in the minimum-security William Head Institution in the first place.

Zachary Armitage appeared by video in the Western Communities provincial courthouse Monday.

Armitage was serving nearly 14 years for robbery and aggravated assault when he and fellow inmate James Lee Busch, 42, escaped from the Metchosin prison on July 7.

The provincial court judge stopped the sentencing hearing Monday in order to solicit a response from Correctional Services Canada explaining why Armitage was sent to the minimum-security prison.

"Has the system failed him, or has he failed the system?" the judge asked the court. “I’m bewildered we’re in this position right now.”

A new sentencing date has been set for Oct. 17 to give the corrections service time to respond to the court's request.

"Any person of his history shouldn’t have been placed in William Head, a jail easy for him to walk away from,” the judge added. 

Crown counsel is asking for a maximum sentence of 24 months for the escape while Armitage's defence lawyer is asking for six to nine months.

After their escape, Armitage and Busch evaded police for two days until the men unwittingly struck up a conversation with an off-duty Mountie in Esquimalt, and were subsequently apprehended.