New documents filed in the ongoing Federal Court dispute between Jacqueline Henderson (Jackie O) and ARN Media have revealed two significant developments: a $3 million company-funded share loan at the centre of a fresh legal claim, and a court order requiring Henderson to undergo a medical examination chosen by ARN’s legal team.
READ MORE: ARN settles with Kyle Sandilands for $12.09 million
READ MORE: We asked a lawyer to unpack Jackie O’s $82m case
The $3 million share loan
When Henderson signed her broadcasting contract with Commonwealth Broadcasting Corporation (CBC) in October 2023, ARN Media provided her company, Henderson Media Pty Ltd, with a $3 million loan to purchase ARN shares.
Under the Loan Share Agreement, the loan was not required to be repaid unless Henderson was deemed a “bad leaver” – defined as a situation where Henderson Media materially breached the agreement, or where Henderson walked away from her contract without cause.
On 29 April 2026, ARN’s board declared that a bad leaver event had occurred.
On 5 May 2026, ARN sold the shares and applied the proceeds to recover the loan.
Henderson’s amended statement of claim disputes the declaration. Her lawyers argue CBC – not Henderson – terminated the contract unlawfully, meaning the bad leaver clause was never validly triggered.
The filings include a standalone claim against ARN for the value of the shares, estimated through to the contract’s original end date of 31 December 2034.
Medical examination ordered
The new court orders also require Henderson to attend a medical examination before 20 July 2026. The examining doctor is to be selected by CBC and ARN’s legal representatives.
The order indicates the radio companies intend to contest the extent of any harm Henderson claims to have suffered. Her statement of claim includes compensation for “pain, suffering, hurt, humiliation and distress,” in addition to financial losses under the contract.
Kyle and Jackie O during the chat which saw Jackie walk. Source: Instagram
What happened on air
The dispute traces back to a live broadcast on 20 February 2026, during which co-host Kyle Sandilands aggressively berated Henderson on air, calling her “off with the fairies” and “almost unworkable” over her interest in astrology and horoscopes.
Henderson, visibly distressed and holding back tears, left the studio and did not return to the air.
Henderson’s lawyers subsequently sent CBC a formal workplace complaint on 26 February 2026.
Rather than addressing it, CBC terminated her contract on 3 March 2026, alleging Henderson had walked away from the agreement.
Henderson denies that characterisation, arguing the complaint sought an alternative show arrangement expressly permitted under the contract.
Total compensation sought across all claims is at least $82.25 million, excluding GST.
ARN and CBC have filed a cross-claim against Henderson, the details of which are not yet publicly available.
A two-week trial is scheduled to begin on 12 October 2026 before Justice Stewart.
Sandilands settlement draws a line
Separately, ARN Media confirmed in an ASX statement on 24 June 2026 that it had reached a binding settlement with Sandilands, bringing to an end all outstanding Federal Court legal proceedings between the parties.
The settlement includes a three-year financial arrangement comprising cash payments, advertising credits, and a revenue share from Sandilands’ future ventures.
ARN will pay Sandilands $12.09 million in total, with $3 million due in July 2026 and the balance paid in monthly instalments through to June 2029.