While a serial pedophile had not committed a crime for decades, questions have been asked about how long he should be watched in the community given a lingering sexual attraction to children.
Alexandria Brookes was first convicted in August 1986 for sexually assaulting a young child in a public toilet.
He formed a relationship with another sex offender while in jail, and the two of them then lured three more children into a toilet block in July 1987 after their release.
Brookes, who is now almost 60 years old, was sentenced to 11 years behind bars for those horrendous crimes.
He again sexually abused a child in a toilet block in 2001 after being released.
After walking from prison once more in 2004, he has been subject to a number of strict conditions to ensure he is monitored safely in the community.
On Tuesday, he was back in the NSW Supreme Court as the state government sought to impose yet another extended supervision order for protection while Brookes lived at an aged care facility.
Justice Richard Button noted that life for the notorious pedophile had proceeded without incident since the last two-year ESO was imposed in June 2022.
"This man sadly is quite physically disabled but there are signs that his attraction to children retains its chronicity," he said.
However, he asked how long such orders could be made and whether the court could restrict Brookes' freedom indefinitely given he had not been convicted of a sexual crime since 2001.
"Chicken and egg conundrum - should the fetters on liberty continue for fear that if they are removed, something bad might happen?" he asked.
While Brookes had committed the child abuse almost 25 years ago, there were concerns his sexual interest in children remained unabated or at least lingering, Justice Button noted.
Representing NSW, barrister Peter Aitkin said Brookes only posed less risk now because of strict conditions on his daily activities as well as the libido-suppressing medication he had to take.
There was no evidence to show Brookes' physical health had declined to the point where supervision was not necessary, Mr Aitkin said.
"And perhaps … a person presenting as physically debilitated might be regarded by an unsuspecting community member to present less of a threat or a concern," he said.
Brookes' barrister Emmanuel Kerkyasharian said his client did not oppose an interim supervision order.
However, he stressed that his client would contest any longer-term restrictions.
In ordering a 28-day ISO starting on June 9, Justice Button noted Brookes' tragic background where he was abused himself as a child.
This violent event "imprinted" itself on the now convicted pedophile, the judge said.
"What has resulted is a chronic sexual attraction to children that can be thought of as pedophilia and he has shown in the past that he is prepared to act on it," Justice Button said.
As well as being "quite severely physically disabled," Brookes was also cognitively impaired showing signs of schizophrenia, the judge said.
Brookes' openness about his sexual desires could have been a result of these cognitive conditions, Justice Button noted.
A final hearing has yet to be set when the state will put on more psychiatric evidence and seek to place Brookes under two more years of supervision.
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028