An arsonist has been confronted at sentencing by a judge who found she used artificial intelligence to pen apology letters for burning down her rental property and assaulting first responders.

Judge Tom Gilbert was unimpressed when he made the discovery after reading Michae Ngaire Win’s correspondence and putting it through ChatGPT software to test its authenticity.

Win was being sentenced for arson, burglary, common assault and resisting police in the Christchurch District Court this week when she was called out and questioned by the judge.

“It is clear these letters were generated by AI [artificial intelligence],” Judge Gilbert said, as defence lawyer Cindy Lee told the court Win had written letters of apology.

Lee then approached Win in the dock, who admitted she had used AI to “help” write the letters.

Lee submitted that some defendants were unable to find the right words when penning such material and would seek help from other sources.

“With the advent of technology, I think people don’t need to be blamed for using it [AI].”

Judge Gilbert didn’t accept her explanation, saying the use of AI to draft apology letters “undermines the sentiments”.

‘I’m going to f***ing kill you’

According to the summary of facts, Win, 37, was living at a Christchurch address when she started a fire in the house in June 2024.

She took a rope and put it in the fireplace, then trailed it out onto the floor to various piles of clothing which led to her bedroom.

Win also used a lighter to set fire to the clothes, and then lay down in her bed.

When Win found the heat unbearable, she broke a window to escape the house.

However, she went back inside a few moments later to retrieve a 9g bag of cannabis and a pair of trousers.

She then made her way out of the house again, and along a road where she called out to strangers for help.

They gave her some clothes and offered to call her an ambulance, but she declined.

Win later told police she didn’t care about the house.

Three months later, in October, she entered a mechanic’s workshop in Murchison and took registration plates from a vehicle and attached them to her own.

Michae Ngaire Win was sentenced in Christchurch District Court. Photo / NZME

The following day, she parked in the driveway of a Kawatiri-Murchison Highway property and waved down motorists who, in turn, called police, telling them that Win claimed she had been assaulted.

Police and Hato Hone St John staff arrived, and when Win was offered assistance, she refused.

As a police officer tried to negotiate with Win, she screamed at him, “I’m going to f***ing kill you”.

When the officer told her she was under arrest, Win anchored herself in her car.

She pulled against the officer’s attempts to pull her out. Once she was out and restrained, she pushed an officer.

Win then kicked the ceiling inside a police car and stood up out of the door space. An officer pulled her to the ground and applied leg restraints.

She was put in the back of the police car, where St John paramedics attempted to help her when she spat in the face of one of them.

In January 2025, Win was back in Christchurch with an active warrant for her arrest.

When police found her, she tried to walk away before she was placed in handcuffs.

At the police car, Win fell to the ground and put her legs on the vehicle to resist getting into the back seat.

Cop traumatised after bite to arm

At the Christchurch Police Station, following a search, she bit an officer’s arm.

Judge Gilbert said the officer had to spend two months on light duties, and the incident had significantly impacted her life.

“She was very worried, and you said you took delight in telling her you had Aids.”

In her submissions, Lee asked for a sentence of home detention coupled with an order for reparation for Win.

Judge Gilbert suggested the cost to replace the four-bedroom house would be $500,000 or more.

He said the property was completely destroyed and underinsured.

“The demolition cost alone was $29,000, which was not covered.

“While the property was destroyed, there was an active mortgage, there was nothing to offset the cost.

“Between the insurance company and victims, they will have to pay $29,000 and rebuild which will likely be in excess of $500,000.”

AI apology letter a ‘tricky’ situation

Crown prosecutor Jade Lancaster said it was the first time she had seen an AI-generated apology letter, and that it could be a problem going forward.

Judge Gilbert described it as “tricky”.

“I don’t think poorly of her for using AI, it is actually a good tool, not all of us are as good with words as others.”

Lancaster accepted that Win’s use of AI didn’t mean she wasn’t remorseful but did denounce the effort of having to write a letter.

A police prosecutor, who dealt with the police charges, said Win had offered to pay reparation but had not saved any money to do so since entering guilty pleas in March 2025.

Lee said Win was now living with her parents on the West Coast and was supported by her mother in court who had offered her address for a sentence of home detention.

“She is off the drugs and has a clearer mind, even though she hasn’t saved money up [for reparation], it doesn’t mean she is not remorseful.”

Mental health not a key factor

Judge Gilbert said Win’s mental health was not significant in terms of sentencing.

“This was a person, because of her own sad life at the time, made a deliberate decision to burn down a house.

“You don’t have a major mental illness; you have been using illicit drugs over a long period.

“You were experiencing acute deterioration of mental health; life was at a low ebb for you, and I accept that there was substance abuse and some other stressors.”

Judge Gilbert adopted a starting point of three years and nine months’ imprisonment.

He applied a 15% discount for guilty pleas, 20% for background and mental health, and 5% for remorse.

Win started sobbing as Judge Gilbert told her she would be going to jail.

While a pre-sentence report had recommended home detention, Judge Gilbert instead imprisoned her for 27 months.

She was also ordered to pay $3000 in reparations.

Al Williams is an Open Justice reporter for the New Zealand Herald, based in Christchurch. He has worked in daily and community titles in New Zealand and overseas for the last 16 years. Most recently he was editor of the Hauraki-Coromandel Post, based in Whangamatā. He was previously deputy editor of the Cook Islands News.