Sorry seems to be the hardest word: Judge rejects AI apology


A judge in Christchurch, New Zealand, has rejected a woman’s apology letter for arson, claiming that “it is clear these letters were generated by AI.”

The recent court case was settling a crime, dating back to June 2024, in which Michae Ngaire Win set fire to her Christchurch rental home by trailing a rope from the fireplace to piles of clothing, as she was high on cannabis.

Furthermore, she used a lighter to ignite clothes leading to her bedroom, then lay down in bed. As the site became unbearably hot, she proceeded to break a window in order to escape.

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Realizing she had left her cannabis and pants in the burning building, she reentered the house to retrieve her possessions. Upon exiting once again, Win began to scream for help, with the intention of alerting her neighbors. She was given clothes, but rejected the offer of calling an ambulance.

The AI apology letter

There were mixed feelings in the courtroom when it became apparent that the defendant, Win, had used ChatGPT to write an apology letter to those affected by her actions, New Zealand media has reported.

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

Meanwhile, Judge Gilbert intervened and indicated that using AI to apologize “undermines the sentiments” and does not convey true remorse that could influence a reduction in a prison sentence.

However, the judge did concede:

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.

Crown prosecutor Jade Lancaster looked at the situation more broadly, acknowledging that this was the first time she’d seen self-reproach through artificial means, but that it could be dire if this became the norm.

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Trial by fire and fraud

In a separate incident, three months later, Win entered a mechanics workshop and stole a registration plate, attaching it to her own car.

Parking up, Win waved down motorists, falsely claiming she had been assaulted. When the police arrived and offered her support, Win wailed, “I’m going to f***ing kill you!”

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After she got back inside her vehicle, the officer informed Win that she was to be placed under arrest, but she refused to exit her vehicle.

Once they managed to yank her out, she pushed a police officer before they applied leg constraints. As the paramedics arrived, she spat in the face of one of the staff.

An ambulance driving to an accident.
Nurphoto via Getty Images

Questionable behavior again upon arrest

In January 2025, when a warrant was sanctioned for her arrest, Win tried to flee the scene before the officers restrained her once again.

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Later at Christchurch Police Station, as a search was conducted on Win, she maliciously bit into an officer's arm.

Judge Gilbert at the court ruled that the officer had to be on light duties following the attack, and that “She was very worried, and you said you took delight in telling her you had Aids.”

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With regard to the burning house, the defense lawyer, Cindy Lee, attempted to secure a punishment of home detention, coupled with payment of damages.

However, with the property uninsured and costing approximately $17,000 to demolish and $300,000 to rebuild, the cost was deemed too high for Win to afford.

Instead, Judge Gilbert ordered her to pay roughly $1800 in damages and to accept a 27-month prison sentence, which may be reduced for guilty pleas and mental health considerations.


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