In 2017, Rudy Giuliani walked into an Apple store in downtown San Francisco looking for help. Giuliani—President Trump’s newly appointed cybersecurity adviser—had locked himself out of his own iPhone. Trump’s technically challenged personal attorney had entered the wrong passcode in his phone at least 10 times, according to an internal Apple store memo obtained by NBC News. While Giuliani’s inability to secure his own device is troubling, what most concerns federal cybersecurity experts is his means of addressing the problem. “There’s no way he should be going to a commercial location to ask for that assistance,” E.J. Hilbert, a former FBI agent for cybercrime and terrorism, told NBC. Michael Anaya, a former FBI supervisory special agent who led a cyber squad for four years, said White House staffers, not Apple store employees, should be helping Giuliani deal with any technical difficulties. “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 said.