Screenshots are forever: ARN WhatsApps enter Jackie O’s $82m fight

Screenshots, it turns out, are forever - even the ones sent in an executives-only group chat.

The contents of WhatsApp group chats between ARN executives may become key evidence in Jackie Henderson's $82 million legal case against the audio network.

In the legal battle between Henderson and ARN Media over the abrupt end of the Kyle and Jackie O show, the Federal Court has ordered the company to disclose details of its meetings with online activist group Mad Fucking Witches, board discussions about the decision to dump the pair's contract, and drafts of its dramatic ASX announcement of Henderson's departure.

Handed down by Justice Wendy Abraham, the ruling also means emails, phone records and WhatsApp messages exchanged between ARN's board and CEO Michael Stephenson in the days around the split will have to be disclosed.

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How the Kyle and Jackie O split unravelled

Henderson's final broadcast alongside Kyle Sandilands aired on 20 February 2026, following an on-air dispute over her interest in astrology. ARN announced her departure to the ASX less than two weeks later, on 3 March 2026 - a statement Henderson's statement of claim alleges misrepresented the circumstances of her exit. 

She is seeking $82 million for the balance of her contract, arguing ARN terminated her services agreement after she raised concerns about Sandilands' on-air conduct and exercised her workplace rights. Sandilands himself has since been subpoenaed to give evidence at the trial, set down for October 2026.

Mediaweek put the disclosure order, and what it could mean for both sides, to Nicholas Stewart, legal expert and Dowson Turco Lawyers partner. Here's what he had to say.

Mediaweek: How significant could the WhatsApp messages between ARN executives ultimately be to Jackie Henderson’s case? What would you be looking for in those conversations if you were acting for her?

Nicholas Stewart: I would be looking for evidence of influence by third parties, discussions by the Board about her complaint to ARN and decision to terminate, previous drafts of any public communications about the matter, and general discussions about managing the matter, including risks to ARN.

Mediaweek: If the private messages reveal executives speaking differently behind closed doors from the position ARN has taken publicly or in court, how damaging could that be - even if none of the individual messages amounts to a legal “smoking gun”?

Nicholas Stewart: This could be very damaging from an ASX disclosure perspective, although we do not know what has been said by whom, or if anything contradictory was discussed behind closed doors. Once an entity is or becomes aware of any information concerning it that a reasonable person would expect to have a material effect on the price or value of the entity’s securities, the entity must immediately tell ASX that information. Section 677 of the Corporations Act defines material effect on price or value. 

For the purpose of sections 674 and 675, a reasonable person would be taken to expect information to have a material effect on the price or value of securities if the information would, or would be likely to, influence persons who commonly invest in securities in deciding whether or not to subscribe for, or buy or sell, the first-mentioned securities. In the legal proceedings, revelations of contradictory statements may be used by Jackie O’s legal team to attack the credit of witnesses or make submissions relating to breaches of her contract (which I am not privy to).

Mediaweek: This case appears to be moving beyond what happened to Henderson and towards what senior ARN executives knew, discussed and decided internally. Does that potentially change the case's legal complexion?

Nicholas Stewart: At this stage, I look at this aspect of the matter as part of the course of litigation. Parties will almost always seek discovery in litigation, meaning they will request documents from the other side that may be relevant to the case, and may obtain subpoenas from the Court to produce categories of documents. What is interesting here is that the respondent is an ASX-listed entity, with significant continuous disclosure obligations. 

If the WhatsApp messages reveal factual matters contradictory to ARN’s public statements, ASIC may look further at ARN’s conduct. It is too early to tell, and we should wait and see what happens in the litigation, noting that the messages will be subject to a claim of confidentiality by ARN.

Mediaweek: ARN has now been ordered to disclose material relating to senior executives’ communications and meetings. How broad can discovery become in a case like this - and at what point can WhatsApp messages, texts, deleted conversations or personal devices become fair game?

Nicholas Stewart: Electronic conversations are always fair game in litigation, where the communications may evidence a fact in issue in dispute. Discovery can be very broad indeed.

Mediaweek: Stepping away from Henderson and ARN specifically, what should media executives and agency leaders take from this case about using WhatsApp for sensitive workplace conversations? Is there still a misconception that an informal or private group chat somehow sits outside the reach of litigation?

Nicholas Stewart: We are in an age of having multiple communication platforms. In my business alone, we keep all business-related communications in Microsoft Teams. Businesses must consider how management and staff communicate about business matters, where that information is stored, and how the communication is checked. I think the issue is that WhatsApp is such an easy method of instant messaging, and has some encryption, that people may think it gives rise to confidentiality. 

But that could not be further from the truth. WhatsApp communications also lend themselves to casualised language and a false environment of freedom to speak without a filter. I think this is where it is a risky form of communicating because, while all electronic communications could find themselves the subject of a subpoena or notice to produce, email communications within a business’s professional platform will naturally be more formal and considered, compared to WhatsApp, Wickr, Telegram, iMessage or even Instagram, Snapchat and Facebook.