Human error, hackable world
Scott Shapiro’s "Fancy Bear Goes Phishing” reveals why our biggest cybersecurity threats aren’t machines—but ourselves.
Fancy Bear Goes Phishing: The Dark History of the Information Age, in Five Extraordinary Hacks
By Scott J. Shapiro
“Hacking is not a dark art, and those who practice it are not four-hundred-pound wizards or idiot savants. Hackers have names and faces, mothers and fathers, teachers, buddies, girlfriends, frenemies, colleagues, and rivals.”
In Fancy Bear Goes Phishing, Scott J. Shapiro delivers an in-depth exploration of a topic many of us seldom think about, but one that has enormous implications for our lives: the human vulnerabilities that lie at the heart of cybersecurity breaches.
Drawing on his popular Yale University course on hacking, Shapiro recounts five significant cyberattacks, revealing how human psychology and social systems often pave the way for digital intrusions. His work underscores the growing need to understand the intersection of technology and human behavior in our increasingly connected world.
What’s the big deal?
Shapiro’s central thesis is clear: cybersecurity failures are less about faulty technology and more about flawed human behavior.
He illustrates this through the infamous 2016 breach of the Democratic National Committee by the Russian hacking group known as Fancy Bear. Despite sophisticated security systems, the hackers gained access by sending well-crafted spear-phishing emails that preyed on basic human trust and error. The attack didn’t require advanced technical wizardry—just a clever manipulation of people. That’s Shapiro’s larger point: the weakest link in cybersecurity is often us.
What I enjoyed most
Two of my favorite subjects in college were physics and mathematics. One figure I discovered—and briefly became obsessed with—was Hungarian-American mathematician John von Neumann. He’s widely regarded as one of the brightest minds in modern science, with work that touched nearly every area of technology and theory. He developed the mathematical framework for quantum mechanics, pioneered game theory, and laid the foundation for digital computing.
So I was thrilled that Shapiro credited von Neumann for his role in developing the stored-program architecture that revolutionized computing by allowing data and instructions to reside in the same memory space. While this innovation was groundbreaking, it also inadvertently introduced security vulnerabilities—enabling malicious code to be stored and executed within systems. In other words, von Neumann’s brilliance not only shaped modern computing—it also gave hackers an opening.
Five takeaways
Human behavior is the primary target: Cyber attackers routinely exploit psychological weaknesses, which makes user education and awareness just as critical as firewalls and encryption.
Past hacks inform present threats: Studying major cyberattacks reveals recurring patterns and informs smarter security strategies.
Tech alone isn’t enough: Effective cybersecurity requires more than technical fixes—it demands thoughtful policy, legal clarity, and cultural change.
Foundational design carries risk: The architecture of modern computers offers power and flexibility—but also creates new opportunities for exploitation.
Cybersecurity is interdisciplinary: Tackling these challenges requires insights from computer science, law, psychology, and even philosophy.
Final thought
I honestly can’t remember where I first heard about Fancy Bear Goes Phishing, but I’m glad I did. The book pulled me in with gripping stories and left me thinking deeply about how we approach digital security. For anyone interested in understanding the complex, human-centered reality of cyber threats, this is an indispensable read.