Extended Supervision Orders: Complete guide in New South Wales

Simon Monteiro, known in the media as the "playboy rapist', recently appeared before the Supreme Court of New South Wales in October 2025 seeking to have his Extended Supervision Order (ESO) revoked.

Following the making of an extended supervision order made by the the State of NSW against Mr. Monteiro, there has been a long history of litigation between Mr Monterio and the State of NSW concerning the conditions and the continuation of his ESO.

The ESO was made on 6 July 2020 after Mr Monterio completed a lengthy sentence for a violent sexual assault of his then partner in an apartment in Bellevue Hill in January 2008. Since that time, he has been convicted of breaching numerous conditions of the ESO, successfully appealed the sentence for the breaches, and served terms of imprisonment for the breaches. He has also successfully applied for the conditions of the ESO to be relaxed.

What is an Extended Supervision Order?

An Extended Supervision Order (ESO) is an order made by the Supreme Court of NSW pursuant to the Crimes (High Risk Offenders) Act 2006 (NSW) ("CHROA'). It allows for the ongoing supervision of an offender who has been released from custody after serving an imprisonment sentence for a "serious offence'.

How Long Can an Extended Supervision Order Last For?

An ESO can remain in force for up to five years pursuant to section 10(1A) CHROA. if a person subject to an ESO is returned to prison, the ESO is suspended and resumes when they are released. When an ESO expires, it is not uncommon for the State to apply for a new ESO.

Before an ESO is made, an offender is usually subjected to an Interim Supervision Order (ISO).

How is an Extended Supervision Order Made?

An extended supervision order under Part 2 of the Crimes (High Risk Offenders) Act 2006 (NSW) ("CHROA') can be made only in respect of a "supervised offender' as defined in Part 2 of CHROA. Once an ESO application under Part 2 is made under Part 1A CHROA, the Supreme Court may make the order under section 5B CHROA if the unacceptable risk criteria are satisfied.

When determining such an application, the Supreme Court must consider the safety of the community as the paramount consideration under section 9(2) CHROA and section 9(3) non-exhaustive matter.

In the case Wilkinson, the Supreme Court of NSW discussed the principles and the provisions of the Crimes (High Risk Offenders) Act 2006 (NSW) that guide when an ESO should be made.

The Court must be satisfied that:

1. The offender (at least aged 18 years) is serving or has served an imprisonment sentence for a "serious offence" by way of full-time imprisonment or an intensive correction order. A "serious offence" means a "serious sex offence" or a "serious violence offence." Once this is established, the Court's power to consider if an ESO should be made is enlivened; and
2. The offender is a "supervised offender' within the meaning of section 5I of CHROA. A "supervised offender' is an offender who, when the application is made, is in custody or under supervision, while serving an imprisonment sentence for a "serious offence", "offence of a sexual nature", offence under section 12 (supervision order breach) or under an existing Interim Supervision Order/ESO/Interim Detention Order/Continued Detention Order. A "serious offence" means a "serious sex offence" or a "serious violence offence".
3. There is a "high degree of probability" that the offender poses an "unacceptable risk" of committing another serious offence if not kept under supervision under the ESO.

Importantly, section 5D states that the Supreme Court does not have to be satisfied that it is more likely than not that the person will commit another offence. In other words, the Court can find that an offender poses an unacceptable risk even if that risk is below 50%- setting a low bar for making such an order against an offender.

Section 9(2) states that the safety of the community must be the Court's "paramount consideration" in determining whether anESOshould be made. This is also reflected in the stated objectives of the Act in Section 3 of CHROA.

Section9(3) specifies a list of matters to which the Court can consider in deciding if there is a "high degree of probability" of "unacceptable risk" including:

• Expert reports and psychological assessments;
• Statistical data detailing the likelihood of reoffending by persons with histories or characteristics similar to that of the offender;
• Reports by Corrective Services NSW;
• information about the offender's participation in rehabilitation programs;
• The views of the sentencing judge for the original offence;
• The offender's criminal history; and,
• Any other relevant information.

When Mr Monteiro's ESO was made in 2020, the Court considered his extensive history of violent behaviour, previous convictions, and reports to police, as well as expert evidence diagnosing him with a "severe personality disorder." The Court concluded that he fell within "the highest category of risk for reoffending" and that there was a high degree of probability that he posed an unacceptable risk if not supervised.

The evidence considered when determining if an ESO should be made is often voluminous and complex and requires careful analysis of expert evidence and a comprehensive understanding of the laws.

What conditions can be attached to an ESO?

Section 11 gives the Court broad discretion to impose a wide range of conditions to manage risk.

Conditions may include requirements that the offender:

1. Not change their appearance without prior approval (State of New South Wales v Fayad (Variation of Conditions) [2021] NSWSC 600 [46] [49]).
2. Not associate or communicate with certain people, including face to face, through written correspondence or electronic means (State of New South Wales v Fayad (Variation of Conditions) [2021] NSWSC 600 [40] - [45]).
3. Inform Enforcement Officers of the name and contact details of any person with whom the offender has started an intimate or sexual relationship within 24 hours (State of New South Wales v Monteiro (Final) [2020] NSWSC 88, Schedule A, [15]).
4. Wear electronic monitoring equipment (State of New South Wales v Monteiro (Final) [2020] NSWSC 88, Schedule A, [4]).
5. Live only at an approved address, not spend the night away without approval, and not permit any person to stay overnight without prior approval and communication of the visitors name and contract details (State of New South Wales v Monteiro (Final) [2020] NSWSC 88, Schedule A, [6] - [9]).
6. Communicate details of any new employment and provide contact details of the person providing the employment (State of New South Wales v Monteiro (Final) [2020] NSWSC 88, Schedule A, [13]).
7. Surrender all passports, comply with directions not to go to a particular place, and not leave NSW without prior approval (State of New South Wales v Monteiro (Final) [2020] NSWSC 88, Schedule A, [10] - [13]).
8. Communicate details of all electronic devices, phone numbers, email addresses and social media accounts, login details and allow officers to inspect all accounts to ensure compliance with the ESO (State of New South Wales v Monteiro (Final) [2020] NSWSC 88, Schedule A, [17] - [23]).
9. Not leave the perimeter of their approved residence unless that are in the "line of sight" of a supervising Corrective Services officer (State of New South Wales v SLD (Preliminary) [2023] NSWSC 330 [49]).

The Court must imposethe least restrictive conditionsnecessary to address the risk posed by the offender and avoid unjustifiable restrictions on liberty (NewSouthWalesvSotheren(Preliminary)[2018] NSWSC 754 per Johnson J at [25]).

What happens if you breach an ESO?

Under Section 12 of theCrimes (High Risk Offenders) Act 2006 (NSW), breaching an ESO is acriminal offence, punishable by up tofive years imprisonment, a fine, or both.

In 2021, Mr Monteiro was sentenced in the District Court totwo years and eight months' imprisonment, with anon-parole period of two years, for breaching multiple conditions of his ESO and ISO. On appeal, the NSW Court of Criminal Appeal reduced this to afixed term of 18 months.

Extended Supervision Orders are one of the most serious post-sentence orders available under NSW law. They are designed to balance the protection of the community with the rights of offenders who have completed their sentences.

If you or someone you know is subject to an ESO or facing an application for one, it is vital to obtainexpert legal advice. The legislation is complex, the evidence involved is detailed, and the consequences of non-compliance can be severe.

The content of this article is intended to provide a general guide to the subject matter. Specialist advice should be sought about your specific circumstances.