The Duke of Sussex has been ordered to explain why messages with his ghostwriter were destroyed after the publication of his memoir Spare when they could be relevant to his legal battle with the publishers of the Sun.

Prince Harry was also told to attempt to retrieve the messages from the messaging service Signal, and his lawyers ordered to search through his other texts, WhatsApp messages and emails from 2005 to January 2023, when his bestselling autobiography was published, for relevant documents.

Anthony Hudson KC, for News Group Newspapers (NGN), accused the duke of “obfuscation” and creating an “obstacle course” during its efforts to find relevant material for the litigation over the prince’s allegations of unlawful information gathering. Harry had to be forced “kicking and screaming” to carry out searches of his communications, Hudson told the high court judge Mr Justice Fancourt on Thursday.

At the one-day hearing, NGN argued the Signal messages between 2020 and 2023 were important because Spare contained extensive references to the duke’s knowledge and suspicion of unlawful information gathering before 2013, the applicable date in the case.

Any claim for damages must be lodged within six years, with Harry having launched his legal action in 2019. If he believed he had a potential claim against NGN before 2013, then the case could be dismissed on the grounds it was filed too late.

In his oral ruling, the judge described “troubling evidence” that a “large number of potentially relevant documents, confidential messages between the claimant and his ghostwriter [JR Moehringer] of Spare, as well as all the drafts of Spare, were destroyed sometime between 2021 and 2023, well after this claim was under way”.

It was not clear “what exactly happened and needs to be made so by a witness statement by the claimant himself explaining what happened to the Signal messages between him and his ghostwriter and whether any attempts have been made to seek to retrieve them”, Fancourt added.

“It seems to me inherently likely that in the course of discussing at length the material for the duke’s autobiography, matters would have been said that related to the parts of Spare in which unlawful information gathering in relation to newspapers is discussed.”

He said Moehringer had written in a New Yorker magazine article that he and Harry “were texting around the clock”. The judge ordered the duke’s lawyers to search texts, WhatsApps and Signal messages as well as Harry’s laptop for relevant documents from 2005 to the end of January 2023, which was the date of publication of Spare, using 47 keywords.

He said attempts should be made to retrieve the Signal messages that were believed to have been deleted.

The judge also expressed “real concern” that the majority of searches for relevant documents had been conducted by “the duke himself in California”, rather than by his solicitors. He said that apart from the articles Harry complained about, and documents relating to his earlier application for the case to be dismissed, the duke had “only disclosed five documents”, adding: “That is rather remarkable and gives me cause for concern about the disclosure exercise.”

Harry, 39, alleges he was targeted by journalists and private investigators working for NGN, which also published the now defunct News of the World. He is among a number of people to bring cases against the publisher, with a full trial of some cases due to be held in January.

The publisher has previously denied unlawful activity took place at the Sun.

David Sherborne, representing Harry, said the autobiography was “written in hindsight” and was not evidence of his “contemporary” state of knowledge. He dismissed the defendant’s application as a “classic fishing expedition” for potential information that was “entirely unnecessary and disproportionate”.

It was “monstrously” inaccurate and headline-grabbing for NGN to allege the duke had to be dragged “kicking and screaming” to disclose documents, he said. Harry was voluntarily allowing a search of his emails that had taken 150 hours and cost £50,000.

He said NGN had previously deleted “millions of emails” as a way of “hiding incriminating evidence”. It was the “height of hypocrisy to suggest that obstacles are being put in the way by the claimant”, he added.

The judge granted NGN’s request that Harry’s lawyers write to his former solicitors at the law firm Harbottle & Lewis and “royal household” members Sir Clive Alderton, the private secretary to the king, and Sir Michael Stevens, the keeper of the privy purse, to request communication records concerning the duke.

Harry was ordered to make an interim payment of £60,000 in legal costs to NGN after a ruling largely in favour of the publisher.

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