Jackie ‘O’ Henderson was complaining about former co-host Kyle Sandilands to their KIIS radio bosses six months before their relationship blew up in the middle of a live show, court documents say.

The revelation was laid bare in a statement of claim filed on Henderson’s behalf in the Federal Court amid her civil case against KIIS-owner ARN Media over the termination of her $100million contract.

ARN axed the record-breaking deal with the radio duo after a segment on the Kyle and Jackie O Show on February 20 where Sandilands slammed Henderson for her ‘fixation’ on astrology.

Henderson said ‘that’s not fair’ and left the studio in tears, before ARN ripped up their combined $200million agreement. Sandilands is suing the broadcaster separately over different grounds.

According to the court documents, obtained by the Daily Mail, Henderson started speaking with the head of KIIS network Derek Bargwanna and executive producer Natalie Penfold about Sandilands’ ‘degrading comments’ in mid-2025.

The complaints began on August 20 when Sandilands referred to Henderson’s ‘psycho babble’ and ‘weird psychological bulls**t’ and allegedly attacked her personal life during a live broadcast.

During that broadcast, he said ‘I am worried about you … that you’ll never find anyone’, ‘your real is not everyone’s real’, and ‘why don’t you just get rid of all of this rubbish that you’ve learnt…and go out and date and let everyone be free’.

He also referred to her ‘period time’.

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Pictured: Kyle Sandilands and Jackie ‘O’ Henderson in the KIIS studio

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Jackie ‘O’ Henderson has followed her former co-host Kyle Sandilands by launching a lawsuit against ARN

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Pictured: A mock-up of text messages between Jackie ‘O’ Henderson (blue) and head of KIIS network, Derek Bargwanna (grey)

Henderson briefly left the live broadcast following those comments in August, before Mr Bargwanna and Ms Penfold went to see her in person.

Henderson and Sandilands had an argument on air three weeks later, on September 10, but Henderson claims Sandilands’ comments were censored out.

At 6.23am that morning, Henderson texted Mr Bargwanna, saying ‘I will not be spoken to the way I was (particularly off air)…’

Almost two hours later, Mr Bargwanna texted Henderson to say Sandilands wanted to share his weight loss success with her.

The message read: ‘Kyle is going to try and call you on air to share good news he lost weight. he wants to be your friend again etc.’

The following day, on September 11, Mr Bargwanna texted Henderson again, saying ‘all ok today?’.

Henderson replied, telling Mr Bargwanna that female listeners were complaining about Sandilands’ behaviour and calling their on-air relationship ‘abusive’.

She also asked that ARN chairman Hamish McLennan and managing director Ciaran Davis be made aware of the situation.

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Kyle Sandilands (pictured outside the Federal Court in Sydney) filed his own lawsuit against ARN in the Federal Court on March 23

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Sandilands has co-hosted The Kyle and Jackie O Show – originally on 2Day FM – since January 2004, before moving to KIIS FM a decade later

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‘Yeah it’s fine today. But let’s make sure Hamish [McLennan] and Ciaran [Davis] start to think about how to address this,’ she told Mr Bargwanna.

‘We are getting a lot of complaints from listeners, calling it an abusive relationship, women especially. I can send you though some [of] the examples.’

In his response, Mr Bargwanna said he had two conversations about the issue with Mr McLennan and Mr Davis.

Their relationship broke down during their final broadcast on February 20, when Sandilands said Henderson’s ‘fixation’ on astrology made her ‘almost unworkable’ – to the point where she left the studio in tears.

Sandilands then said: ‘You can’t start crying about it, it’s not that big a deal.’

According to the court documents, the broadcaster did not attempt to intervene or stop Sandilands.

The following day, on February 21, Henderson texted CEO Michael Stephenson and chief content officer Kerri Elstub, saying Sandilands’ conduct was ‘unfair, inappropriate and completely unprovoked’.

She also asked whether anything had been put in place ‘around boundaries and expectations moving forward’.

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Radio network ARN axed Sandilands’ $100million deal after a segment on the Kyle and Jackie O Show on February 20 when he slammed Henderson (above) for her ‘fixation’ on astrology

On February 26, Henderson’s lawyers wrote a letter of complaint to Commonwealth Broadcasting Corporation – a subsidiary of ARN Media – explaining the broadcaster had been notified about Sandilands’ ‘bullying’.

Henderson also accused the broadcaster of failing to provide a safe work space.

The letter said Henderson ‘could not continue to work with Mr Sandilands’, but that she was willing to continue her contract with a different show.

She had wanted CBC to propose an alternative to the Kyle and Jackie O Show.

CBC’s lawyers replied on March 3, saying Henderson’s letter of complaint equated to the termination of her $100million contract – which she disputes.

Henderson also took aim at an ASX announcement on March 3, when ARN released an announcement titled ‘The Kyle & Jackie O show’.

The announcement said: ‘Ms Jacqueline Henderson has given notice that she ‘cannot continue to work with Mr Kyle Sandilands.’

In her statement of claim, Henderson argued the announcement wrongly conveyed that she terminated her own contract and that she didn’t intend to work for ARN anymore.

She also argued the announcement incorrectly stated she had been offered an alternative show on the ARN network.

Henderson accused the broadcaster of being ‘misleading and deceptive’, claiming she was never offered another show, nor did she give notice to end her employment.

She alleged the termination of her contract was a breach of the Fair Work Act, and is claiming compensation of at least $82.25million.

She is also seeking payment of a pecuniary penalty plus interest and costs.