Inside his Goulburn prison cell, shoplifter Beau Wiles stripped down to his underwear and a cap then somehow took two photos of himself and posted them to Facebook.
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"Love u my my (sic) princess," the 25-year-old one-time aspiring rap artist captioned the pictures - a message to his girlfriend waiting on the outside.
She responded a short time later: "Love u too my prince can't wait to have my hand all ova that sexy body of urz."
Less than 48 hours later, Wiles vanished from the prison grounds, having last been spotted in a work area of the jail at 10am on Wednesday.
Wiles' escape, the second from the Goulburn complex in six weeks, has again raised questions about security at the prison.
More questions are being raised about how Wiles was able to take photographs, make posts to Facebook and communicate with friends online, given internet access is banned for all inmates.
Wiles was serving 18 months in minimum security. But his girlfriend revealed on his Facebook page that they had been making wedding plans.
"Thats my man lookin fresh as always ,,, babie i cant wait to marry you!!! As soon as ur out im gunna make u my husband,xxxx," she wrote.
Wiles, who recorded a rap song, Time To Rise, under the name BEAUJANGLZ in 2012, also kept his family and friends up to date with what he was doing, and eating, while in jail.
"Just finished in the gym having a tuna and bake beans the good stuff u know it ... " he posted at the start of the month.
On Wednesday morning police began a search for Wiles, who was described as being 180 centimetres tall, 100 kilograms, with tattoos on his lower forearms.
A Facebook friend urged him to hand himself in to police.
"Brother please hand ur self in to police now its only jail the is bad beau they will kill u shoot u dead please bro go back to police now please I beg u beau," the poster wrote on Wednesday afternoon.
Wiles' escape follows that last month of armed bandit Stephen Jamieson, 29, who became the first inmate to escape from Goulburn's maximum security section in 19 years.
Jamieson used bed sheets he had tied together to scale the prison walls, and, with a pillow strapped to his waist, manouevred over the razor wire to freedom.
He was on the run for 12 hours before he was recaptured by police following a pursuit in south-west Sydney.
Jamieson was already being held in segregation following suspicions he was behind a man-made hole found on prison grounds earlier in August.
NSW Opposition Leader Luke Foley said it was not good enough that there had been five prison breaks already in 2015-16
"Corrective Services Minister David Elliott is single-handedly solving the overcrowding crisis in NSW prisons by letting inmates stroll out the front gate," Mr Foley said.
"Under Elliott's watch, inmates even have the luxury of bragging about their escape plans on Facebook. It'd be laughable if it wasn't so serious."
In 2014-15, seven inmates escaped from NSW correctives facilities, the lowest number in at least two decades.
In 1995-96 there were 179 escapes.
