Kevin Roose hired a couple of high-end hackers to penetration-test his personal cybersecurity setup. It did not go well, unless you count “realizing that you’re incredibly vulnerable” as “well”. In his write-up of the exercise, Roose mused:

“The scariest thing about social engineering is that it can happen to literally anyone, no matter how cautious or secure they are. After all, I hadn’t messed up — my phone company had. But the interconnected nature of digital security means that all of us are vulnerable, if the companies that safeguard our data fall down on the job. It doesn’t matter how strong your passwords are if your cable provider or your utility company is willing to give your information out over the phone to a stranger.”

There is a genuine tradeoff between safety and convenience when it comes to customer service. Big companies typically err on the side of convenience. That’s why Amazon got in trouble back in January. Most support requests are legitimate, so companies practice lax security and let the malicious needles in the haystack slip through their fingers (to mix metaphors egregiously). If a business like Amazon enacts rigorous security protocols and makes employees stick to them, the average user with a real question is annoyed. Millions of average users’ mild discomfort outweighs a handful of catastrophes.

Artwork by Michael Mandiberg.

Artwork by Michael Mandiberg.

In semi-related commentary, Linux security developer Matthew Garrett said on Twitter (regarding the Apple-versus-FBI tussle):

“The assumption must always be that if it’s technically possible for a company to be compelled to betray you, it’ll happen. No matter how trustworthy the company [seems] at present. No matter how good their PR. If the law ever changes, they’ll leak your secrets. It’s important that we fight for laws that respect privacy, and it’s important that we design hardware on the assumption we won’t always win”

Although Garrett is commenting on a different issue within a different context, I think these two events are linked. The basic idea is that when you trust third parties to protect your privacy (including medical data and financial access), you should resign yourself to being pwned eventually. Perhaps with the sanction of your government.