What else is on Rudy's phone?

Less than a month after he was named President Donald Trump’s cybersecurity adviser in 2017, Rudy Giuliani walked into an Apple store in downtown San Francisco.

He wasn’t looking for a new gadget. Giuliani was looking for help.

He was locked out of his iPhone because he had forgotten the passcode and entered the wrong one at least 10 times, according to two people familiar with the matter and a photo of an internal Apple store memo obtained by NBC News.

“Very sloppy,” said one of the people, 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.”Notes from an internal application that Apple uses for their service tickets show that Rudolph Giuliani came in with a disabled phone. Some personal information in the photo has been obscured by NBC News.Acquired by NBC News

A forgotten password is among the most common missteps in the digital age.

But Giuliani’s handling of the situation calls into question his understanding of basic security measures and raises the prospect that, as someone in the president's inner circle, his electronic devices are especially vulnerable to hackers, two former FBI cyber experts told NBC News.

“There’s no way he should be going to a commercial location to ask for that assistance,” said E.J. Hilbert, a former FBI agent for cybercrime and terrorism.

Michael Anaya, a former FBI supervisory special agent who led a cyber squad for four years, reacted with astonishment when told about Giuliani’s Apple store visit.

“That’s crazy,” he said.
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NBC News reported last week that Giuliani twice butt-dialed one of its reporters, leaving long voicemail messages in which he is heard discussing the Bidens, business in Bahrain and his need for cash.

Both of the accidental calls were made in the hours after Giuliani had spoken with the reporter.

In the first voicemail message left on Sept. 28, Giuliani can be heard bashing Joe Biden and his son Hunter, as well as recounting his effort to push Ukraine to launch an investigation into the Bidens. The second recording, left on Oct. 16, captured Giuliani talking to an unidentified man about Bahrain.

“The problem is we need some money,” Giuliani says in the voicemail message. “We need a few hundred thousand.”
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Giuliani was named Trump’s cybersecurity adviser on Jan. 12, 2017, an informal position outside of the government.

“This is a rapidly evolving field both as to intrusions and solutions and it is critically important to get timely information from all sources,” the presidential transition office said in a statement on that day. “Mr. Giuliani was asked to initiate this process because of his long and very successful government career in law enforcement and his now sixteen years of work providing security solutions in the private sector.”

Exactly 26 days later, Giuliani was among a group of people standing outside the Apple store in San Francisco’s Union Square neighborhood before its doors swung open at 10 a.m., according to a former store employee.
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NBC News sent an email to that personal address Wednesday afternoon with the name of this reporter below a brief message: “Mr. Giuliani — Trying to get in touch with you.”

Two minutes later, a one-word message from the email account landed in the reporter’s inbox: “Why?”

A follow-up email — explaining the details of this article and asking for a response — was not returned. A text message to Giuliani’s cellphone also went unreturned.

Apple did not return a request for comment.

In interviews, the two former FBI cyber experts said the two incidents taken together — Giuliani’s butt dials and reliance on Apple workers to help him reboot his phone — indicate a lax approach to mobile phone security.

“I can understand if you’re an auto mechanic or even a lawyer that these issues are not first and foremost in your mind,” Anaya said. “But I would like to think that for somebody that close to the president, this would be something they would take seriously.”

Anaya said the possibility that Giuliani might be using a personal phone for sensitive communications with the president and others would make him a prime target for foreign hackers.

“If I were a nation-state actor and that information became available to me, one of the first things I’d do is try to install some piece of malicious software that would allow us to see everything that comes in and out of that device,” Anaya said.

Hilbert said he’s also troubled by the fact that Giuliani’s cellphone data is backed up to Apple's iCloud system, even if the former New York City mayor largely uses it as his personal phone.