In early 2017, long before Rudy Giuliani would entangle himself in an international amateur-diplomacy scandal that launched America's fourth-ever presidential impeachment inquiry, the former New York City mayor occupied a more modest and less criminal role in the Donald Trump extended universe: as the head of a presidential working group on cybersecurity. Or as he explained it on Fox & Friends at the time, "security for cyber."

Around the same time, however, the nation's newly-installed expert on protecting U.S. elections from foreign interference was grappling with a much more foundational technology-related problem—one that has vexed countless men and women of a certain age ever since the late Steve Jobs promised to "reinvent the phone" a decade earlier. In February 2017, according to NBC News, Giuliani locked himself out of his iPhone after forgetting his passcode and entering the wrong one at least ten times, and needed someone at an Apple Genius Bar in San Francisco to fix it.

“Very sloppy,” said one of the [NBC News sources], a former Apple store employee who was there on the day that Giuliani stopped by in February 2017.

“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.”

An employee helpfully reset Giuliani's phone, but as the individual quoted above notes, a high-level presidential advisor's cheerful willingness to hand over his iPhone to a stranger in a retail store does not exactly reflect well on his alleged expertise in information security.

This is not the first time that flippant technology use has been an issue for Trump and his inner circle. In 2017, White House tech staffers discovered that then-chief of staff John Kelly's phone had likely been hacked, and that he continued to use the device for months before complaining that it wasn't working properly. In October 2018, the New York Times reported that American intelligence officials warned Trump that Chinese and Russian spies "routinely" listened in on his iPhone calls, but that the president—reluctant to use a government-issued phone that does not allow him to save contacts—had refused to give up his personal device. Although the Department of Homeland Security officials has detected the use of cell surveillance devices in the White House's vicinity, the president has allegedly resisted attempts to regularly swap out the government phone he uses to tweet, explaining that doing so would be "too inconvenient."