For much of the 2000s, President Donald Trump's personal attorney billed himself as a high-level security consultant after presiding as mayor of New York City during the 9/11 terror attacks.
But shortly after being named Trump's cybersecurity adviser in 2017, Giuliani needed cyber assistance of his own to unlock his iPhone after entering the wrong passcode at least 10 times in a row, NBC News reported, citing two sources familiar with the matter and an Apple Store document from the location in San Francisco that Giuliani visited.
Giuliani has long been known for experiencing technical difficulties online on platforms like Twitter, and for accidentally butt-dialing and pocket-dialing reporters.
NBC News reporter Rick Schapiro, the author of the story on Giuliani's Apple Store visit, previously reported that Giuliani butt-dialed him on two occasions in the fall of 2019 and left two three-minute voicemails in which he discussed his foreign business dealings in Bahrain, his need for cash, and his baseless allegations that former Vice President Joe Biden and his son Hunter have engaged in corrupt activity overseas.
Last December, Giuliani accidentally created a hyperlink in one of his tweets ranting about the Mueller probe. A social media user was quick to purchase the domain name "g-20.in" Giuliani accidentally created in his tweet — and trolled Giuliani by making the link lead to a webpage reading, "Donald J. Trump is a traitor to our country."
Giuliani then blamed Twitter for his keyboard mishap, and accused them (and Time magazine) of being biased against Trump supporters. A representative for Twitter said at the time that "the accusation that we're artificially injecting something into a tweet is completely false."
While Giuliani's digital mishaps may be amusing to some, cybersecurity experts told NBC that Giuliani going to a third-party location for technical help violated the most basic protocol even an informal White House adviser should follow.
A former Apple store employee who was present during Giuliani's visit to the Genius Bar told NBC that Giuliani's passcode mistake was "very sloppy," adding, "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."
Former FBI cybercrime agents E.J. Hilbert and Michael Anaya both told NBC that Giuliani even going into a "commercial location" to unlock his device was extremely unsafe, and he should have sought assistance from a qualified White House staffer and not a third-party like a Genius Bar employee.
"It's unnerving to think that this individual has access to the most powerful person in the world and that sensitive communications could be disclosed to people who should not have access to them," Anaya told NBC, further calling it "crazy" Giuliani entrusted his phone to an Apple store.