The man, known for legal reasons as SLD, has spent almost two-thirds of his life in jail after the then-13-year-old abducted and fatally stabbed his three-year-old neighbour Courtney Morley-Clarke on the NSW Central Coast in 2001.
Upon his release in April 2023, he was subject to a slew of strict conditions enforced by community corrections officers tasked with supervising the institutionalised man and protecting the community.
He was jailed again for 18 months in October that year after approaching a mother and her partially undressed 10-month old son at a beach in Wollongong.
The now 39-year-old failed to overturn his conviction for that breach on Wednesday.
Five days after being released in March 2025, he told supervising officers he had again breached his strict conditions.
"Good luck finding anything I do on the phone," he said during a supervised visit to an Optus shop.
On two occasions about a week later, he bragged about being able to delete his internet activity, using the dark web and wanting to access dating sites so he could lose his virginity.
These details come from court documents seen by AAP after SLD pleaded guilty to five counts of breaching supervisory orders and two charges relating to child abuse material.
While free in the community, he had been barred from using social networking services or dating sites without prior approval.
He was also only permitted to view sexually explicit material on a single pornographic website, but he was told not to watch anything involving sexual violence or cruelty towards women or children.
During a subsequent review of his phone, police found he had breached these conditions.
He was then arrested in April 2025.
Examining his phone, officers found one image of a five-year-old girl naked from the waist down.
They also located 43 images downloaded onto his device showing women in sexually violent situations including being tied up, looking scared or in pain and having hands placed over their mouths.
One image was titled "the raped virgin", court documents reveal.
The killer searched for sexually violent material online, including viewing a video claiming to be of a drugged woman raped in a hotel.
He tried to look for child abuse material by searching for terms like "real child rape" on explicit websites.
He further breached conditions by using a fake name to create a Facebook profile and chat with members of the public.
The 39-year-old will be sentenced at Campbelltown District Court in June.
On Wednesday, the NSW Court of Criminal Appeal dismissed SLD's claim his conviction for speaking to the mother and her 10-month-old child in October 2023 was unreasonable.
Justice Phillip Boulten noted the convicted killer was permitted to ask women out on dates and frequently approached them to do so.
"His approaches were not nuanced and were probably unsuccessful," the judge wrote.
In talking to the mother while her child was nearby, the 39-year-old intended to be in the baby's company and thereby breached a restriction on associating with children, Justice Boulten found.
The NSW District Court was correct in convicting him, he said.
The killer had been under supervision by a community corrections officer at the time and was also watched by an off-duty officer who had noticed the ankle bracelet he was wearing.
SLD approached a female cafe worker as well, telling the 25-year-old she looked incredibly young.
He told her he had been in jail since he was 13 years old and was still a virgin.
The killer only recently offered a motive for murdering Courtney: to exact revenge for purported bullying by her brother.
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028
Lifeline 13 11 14
Kids Helpline 1800 55 1800 (for people aged 5 to 25)
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