A former New York Mayor turned current lawyer and informal cybersecurity adviser for US President Donald Trump has had his suitability for the latter role called into question after it emerged he had to go to the Apple store to get them to unlock his phone.
Rudy Giuliani took a trip to the Apple store in downtown San Francisco in February 2017, shortly after he was appointed to the informal adviser role, reports News.com.au.
According to a store memo obtained by NBC News, Mr Giuliani had apparently forgotten his passcode when trying to unlock his iPhone, but kept trying anyway and eventually disabled the device by entering the wrong code too many times.
He took it to the Apple store, where staff "proceeded with a DFU (device firmware update) restore" before setting up "the phone again from a current iCloud backup".
The issue, which Mr Giuliani could have likely solved in less than an hour by googling it, allowed NBC to scoop a second embarrassing tech failure by Mr Giuliani in as many weeks, after he accidentally "butt-dialled" NBC News reporter Rich Shapiro on two separate occasions, each time leaving the reporter three minute voicemails where he's heard discussing a number of sensitive matters.
Mr Giuliani attempted to play off the latest incident with a joke on his Twitter account.
It's understood he was referencing an extensive dispute between Apple and the FBI after the Bureau asked the tech company to unlock an iPhone 5C that belonged to one of the husband-and-wife terrorists behind a 2015 mass shooting in San Bernardino, California.
Apple refused to do so as a matter of principle.
"The US government has asked us for something we simply do not have, and something we consider too dangerous to create … a backdoor to the iPhone," CEO Tim Cook said in an open letter he and other top Apple employees spent the whole night drafting after receiving the FBI's request for help.
The FBI said it needed Apple's assistance because it had no other way to get into the iPhone, though a US Department of Justice report later found the FBI expended more effort trying to force Apple to unlock the phone than it did looking for an alternative itself.
In the end the FBI found another way to unlock the phone without Apple's help.
While Mr Giuliani joked about the parallels between his issue and the FBI's, former Bureau staff didn't see the humour in his trip to the Apple store.
"There's no way he should be going to a commercial location to ask for that assistance," former FBI agent for cybercrime and terrorism E.J. Hilbert told NBC News.
A former FBI supervisory special agent who spent four years leading a cyber squad, Michael Anaya, echoed the statement and said it was "crazy" that Mr Giuliani went to the store for help.
"You're trusting that person in the store not to look at other information that is beyond what you're there to get assistance for," said Mr Anaya. "That's a lot of trust you're putting into an individual that you don't know."
Apple store staff have embarrassed the company on several occasions by disrespecting the privacy of customers, including one 2016 incident exposed by The Courier-Mail where four men were fired from the Carindale store in Brisbane's east for stealing explicit and personal images off customer phones that were then shared with and "ranked" by other staff.
One staff member at the San Francisco Apple store on the day Mr Giuliani visited expressed similar concerns: "Trump had just named him as an informal adviser on cybersecurity and here, he couldn't even master the fundamentals of securing your own device."
Mr Anaya said that the passcode incident combined with the repeated butt-dials indicated Mr Trump's personal lawyer had a lax approach to device security.
"I would like to think that for somebody that close to the President, this would be something they would take seriously," he added.