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Incident Response and Management
Penetration Tests and Red Team Exercises6
Although this is a great list of security controls, companies following them
often do so without grappling with the complexities of human nature.
Even though security experts know well of the riskiness of human
behavior, security rules and practices still aren’t sensitive enough to how,
and how often, people within systems make mistakes.7 Despite the fact that
security professionals know that people are imperfect, security rules and
practices often fail to incorporate this knowledge. Instead, many security
rules and practices are designed for perfect people. These perfect people
learn and remember all of the rules. They always follow the rules, no matter
how inconvenient or difficult they become. They never look at any
irrelevant websites while at work. They never click on any links that are
suspicious. They never cut corners. They carefully listen to their training
and do everything they are told. They are always patient and careful.
But of course, people are far from perfect. Humans mess everything up.
People are in a hurry, they have limited ability to remember things, they
often don’t pay attention and don’t follow rules, and they are prone to trust
when they shouldn’t trust. If people were perfect, most security measures
would work quite well. But it’s nearly impossible to make people perfect; it
is much more feasible to design security measures differently so they work
with people as they are.
Policymakers are not designing data security measures with human
limitations in mind. Instead of assuming the best in people, the law should
prepare for the worst. Even if 99 out of 100 people are perfect, the hackers
still win because they can trick one person. Data still gets lost if one person
loses it. In other words, data security is a game won or lost based on the
most error-prone player on your team. Sadly, on most teams, many people
are competing for the title of “most likely to mess up.” You can’t win the
game by focusing only on the good players. Hackers know this, which is
why they win so often.
 
Figure 8.1
Data security law must confront this reality. Only by accounting for the
most error-prone among us will we stand a fighting chance against the
hackers.
THE BANDWIDTH PROBLEM: WHY WE ASK THE IMPOSSIBLE
WITH PASSWORDS
Imagine that you are starring in a production of Shakespeare’s King Lear,
and you are playing the king. The play starts now, the curtain is rising, but
you haven’t memorized your lines. You look down, and you are wearing
only your underwear. . . .
You may have had nightmares similar to the one above. You are about to
take a test or perform a task, but you are woefully unprepared for it. You are
going to fail, and your best hope is to wake up before it happens. This type
of nightmare, unfortunately, is what we are living in with many data
security measures.
People are Destined to Fail with Passwords
At 33 years old, Christopher Chaney was unemployed and living in his
grandmother’s house. He spent his time watching movies and browsing the
Internet. Having received his first computer just a few years before, Chaney
did not possess any advanced IT skills or fluency in coding. What Chaney
did have, however, was an abundance of free time.8
In early 2008, Chaney heard that nude images of celebrity Miley Cyrus
had been leaked online. Chaney was intrigued by how the images were
obtained. Previously, he had learned that a hacker broke into celebrity Paris
Hilton’s phone by guessing her password—the name of her pet Chihuahua,
Tinkerbell. On a whim, he began to compile a list of celebrities by first and
last names. He then researched their personal information online, arming
himself with data that would help him guess their passwords.9
Chaney worked his way down his list, entering names into Gmail until
he found a valid celebrity email address.10 Once he had an email address, if
he couldn’t guess the password, then he would turn to the “forgot my
password” function. He was presented with personal security questions
required to reset the account password. He then searched online across
various social media platforms and other sites to find information to help
him answer the questions.11 The answers to questions, such as the name of
the celebrity’s pet, were fairly accessible online. When Chaney correctly
answered the password recovery questions, he would reset the account
password to allow him access to the account.12
After breaking into an account, Chaney would change the settings to
automatically forward copies of all outgoing mail to his own email
address.13 When the victims regained control of their accounts, they had no
idea that copies of their email were being forwarded to Chaney. Hardly
anyone routinely checks their forwarding settings.14
Secretly receiving a copy of all emails that the celebrities sent allowed
Chaney to read scores of private email messages to family, friends,
physicians, attorneys, and others. He learned about people’s extramarital
affairs, health issues, and sex life. He could see sensitive information such
as financial data and confidential movie scripts. And he could find the email
addresses of other celebrities in the contact list—his next victims.
His snooping, which began in curiosity, soon turned into a complusion.
He would go on to break into at least 50 celebrity email accounts. In
addition to celebrities, Chaney also started to break into other people’s
accounts.15
Among the information Chaney amassed were nude photos of several
celebrities, including Scarlett Johansson, Mila Kunis, Christina Aguilera,
and Renee Olstead. These images were sent in confidence by the celebrities
to their significant others.16 On several occasions, Chaney sent emails from
his victims’ accounts impersonating the celebrities. He leaked intimate
images that Scarlet Johansson sent to her former husband, Ryan Reynolds.
When their marriage began to dissolve, Chaney read their personal
discussions leading up to their divorce.17
The leaked nude images soon made national headlines. The celebrities
were shocked, devastated, and furious. According to Christina Aguilera,
“[t]he feeling of security can never be given back” and “there is no
compensation that can restore the feeling one has from such a large invasion
of privacy.”18 Scarlet Johansson described Chaney’s actions as “perverted
and reprehensible.”19
After Chaney leaked sexually provocative pictures of Renee Olstead, the