Jackie ‘O’ Henderson isn’t letting her court battle dampen her social life.

The former radio host, who is locked in high-stakes litigation with ARN after the collapse of the Kyle and Jackie O Show, re-emerged into Sydney‘s glamorous nightlife as she attended Australian Fashion Week on Thursday night.

Rushing through the rain surrounded by a protective entourage who covered her under a coat against the downpour, the 51-year-old appeared in good spirits when approached by Daily Mail.

Jackie said she was ‘feeling good’ and doing well in the face of her controversial exit from her top-rated radio gig.

However, when asked how she was filling her free time while unemployed, a minder quickly stated that Jackie was ‘all good’ and would not be drawn any further.

The media personality cut a suitably fashionable figure for the outing, wearing a strapless satin gown with a bustier bodice.

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Jackie ‘O’ Henderson (pictured) re-emerged into Sydney’s glamorous nightlife as she attended Australian Fashion Week on Thursday night

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Rushing through the rain surrounded by a protective entourage who covered her under a coat against the downpour, the 51-year-old appeared in good spirits

The sighting comes as Henderson remains at the centre of a Federal Court case against ARN Media over the termination of her reported $100 million contract, following the collapse of her long-running radio partnership with Kyle Sandilands.

Court documents, filed as part of Henderson’s statement of claim, outline months of internal tension leading up to the dramatic breakdown of the Kyle and Jackie O Show earlier this year.

According to the filings, Henderson raised concerns about Sandilands’ on-air behaviour with KIIS network management months before the relationship publicly deteriorated during a live broadcast in February.

The documents allege Henderson began speaking with senior KIIS executives in mid-2025 about what she described as ‘degrading comments’ made on air.

One August broadcast is cited in the claim, during which Sandilands made remarks about Henderson’s personal life and used language she found offensive, prompting her to briefly leave the studio at the time.

The court material also outlines text exchanges between Henderson and KIIS executives in September, where she reportedly said she would not accept the way she was being spoken to, and raised concerns that listeners were describing the on-air dynamic as ‘abusive’.

The breakdown escalated in February during what would become the duo’s final broadcast, when Sandilands criticised Henderson’s interests on air and suggested she had become ‘almost unworkable’, comments that allegedly left her in tears and prompted her to leave the studio.

According to the claim, ARN did not intervene during the segment.

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The media personality cut a suitably fashionable figure for the outing, wearing a strapless satin gown with a bustier bodice

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View gallery

She added a YSL envelope clutch to her ensemble

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When approached by Daily Mail, Jackie said she was ‘feeling good’ and doing well in the face of her controversial exit from her top-rated radio gig

The following day, Henderson contacted senior ARN executives, describing Sandilands’ conduct as ‘unfair, inappropriate and completely unprovoked’, and questioning what safeguards were in place going forward.

On 26 February, her lawyers formally wrote to ARN subsidiary Commonwealth Broadcasting Corporation alleging bullying and stating she could not continue working alongside Sandilands, while leaving open the possibility of remaining within the network in a different role.

ARN later responded that her letter amounted to termination of her contract, a position Henderson disputes.

She is now alleging the broadcaster engaged in misleading and deceptive conduct and breached the Fair Work Act, and is seeking compensation of at least $82.25 million, plus penalties, interest and costs.

Despite the ongoing legal dispute, Henderson’s public appearance at Australian Fashion Week suggested a composed front as the case continues to progress through the Federal Court system.