As he was being sentenced for breaking into an Albion Park Rail service station in 2020, habitual criminal Kevin Leslie Henry told the judge he was "over it" and had no intention of going back to jail.
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But a year after he was released on parole, Henry committed an almost identical break-in at the same business.
He faced Wollongong District Court again on Friday for sentencing on this later break-in, as well as an armed robbery at another service station.
The first crime occurred about 9.35pm on April 14 last year, when Henry - armed with a metal bar - and another man confronted the lone employee of the Enhance service station in Fern Street, Gerringong.
Henry and his co-offender had their faces covered, with holes cut out for their eyes.
The terrified employee - who had emigrated to Australia from Sri Lanka just six weeks prior - told them to take the cash from the till drawer.
The two criminals pointed at the safe but took the cash and four cartons of cigarettes, which together were worth over $2400.
DNA found on clothing discovered a short distance away was matched to Henry and a vehicle registered to his wife was captured on CCTV in the vicinity of the service station before and after the robbery.
Ten days later, Henry and another accomplice, Keedan Daniels, kicked a hole in the gyprock of the Caltex service station in Albion Park Rail and crawled inside.
Faces covered, they commando crawled along the ground, broke into the cigarette cabinet and stole over 200 packets of cigarettes, worth almost $7500.
But as they crawled back through the hole, Henry's beanie was snagged on the gyprock - and again police found his DNA.
On Friday, Judge Robert Sutherland noted that while Henry's mother was a positive influence growing up, he was exposed to violence, drugs and alcohol use.
He started using cannabis at 12 and heroin in his teens, which became an enduring addiction.
Judge Sutherland outlined Henry's extensive criminal history, which included dozens of offences, including armed robberies and break-ins.
In the last 14 years, he said, Henry had spent just two and a half years outside jail.
In January 2020, Henry smashed a hole in the wall of the Caltex service station at Albion Park Rail, crawled inside and stole cigarettes.
He was jailed for this offence and released on parole in April 2021, a time in which his wife said he was "a different man".
Henry was on a drug treatment program but feeling stable, he ceased - and soon relapsed.
Judge Sutherland expressed pessimism about Henry's prospects of rehabilitation but said there was a glimmer of hope.
He noted Henry had almost successfully completed parole before he committed these most recent crimes.
Henry pleaded guilty to the offences of armed robbery and aggravated break and enter.
Judge Sutherland sentenced Henry to five and a half years' imprisonment, with a non-parole period of three years and nine months.
With time served, he will become eligible for release in three years.
His co-offender in the break-in, Daniels, had earlier been sentenced in the Local Court to an 18-month intensive correction order.
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Natalie Croxon
Reporter at the Illawarra Mercury, mostly covering social affairs. Previously of the Bendigo Advertiser, Northern Daily Leader and Quirindi Advocate. Our Watch award winner.
Reporter at the Illawarra Mercury, mostly covering social affairs. Previously of the Bendigo Advertiser, Northern Daily Leader and Quirindi Advocate. Our Watch award winner.
