Workplace Expectations and Personal Exceptions: The Social Flaws of Email Security

Even though they’ve been around for quite some time, phishing attacks continue to climb. According to Proofpoint’s 2019 “State of the Phish Report,” 83 percent of businesses experienced a phishing attack and 64 percent of security professionals encountered spear phishing threats in 2018. New vectors are also emerging: As noted by Forbes, software-as-a-service (SaaS) credential theft, messaging app attacks and malicious link embedding within shared files are all on the horizon for 2019.

The data begs the question: What’s wrong with email security? For years, thought leadership articles and information security experts alike have been recommending commonsense best practices that should curtail email attack efforts. Don’t click on unknown links. Don’t open unsolicited attachments. Use automated detection tools. And yet phishers are hauling in bigger catches than ever before, expanding their operations to include new threats and grab more data.

I believe the problem is tied to phishing’s fundamental premise: Social barriers are far easier to break than their technological counterparts. By exploiting critical social flaws — specifically, workplace expectations and personal exceptions — attackers can gain the upper hand.

Email Still Reigns Supreme

Despite recent challenges from up-and-comers such as social messaging apps and unified collaboration tools, email still reigns supreme in the workplace. As noted by CMS Wire, “There appears to be a general consensus that while social networks are useful to achieve work-related goals, email remains the undisputed communications tool in the enterprise.”

Email is timely and transparent — users can quickly send and receive information while creating a digital paper trail. Unlike some messaging apps, users can include attachments and draft longer responses and, since email exists outside of most collaboration continuums, employees can temporarily take a break from their inbox.

But that’s not the whole story. For better or worse, corporate email itself is a kind of social network. As Nathan Schneider, a professor of media studies at the University of Colorado, told The New York Times, “Email is the most resilient social network on the internet.” While it lacks the bells and whistles of social media platforms and the intimacy of face-to-face communication, email has evolved its own set of social rules around usage, etiquette and response times. For example, users are expected to create clear subject lines, reply to all emails (even if received in error), limit the amount of humor and restrict the use of punctuation such as exclamation marks, as noted by Inc.

The rise of interactive business email compromise (BEC) attacks also speaks to the social nature of email. New BECs don’t start with malicious payloads, but instead leverage short social messages to compel employee replies and create a compelling, albeit fake, interactive dialogue before dropping infected documents.

Simply put, email is the biggest, most used social network in the enterprise — and that’s not changing anytime soon.

The Psychology of Urgent Requests

The fundamentally social nature of email leads us to our first security issue: expectations.

Consider common phishing security advice that warns against emails marked “urgent” or “DO NOW.” Why the focus? Because humans are naturally conditioned to meet social norms and feel substantial pressure to conform. According to the Havard Business Review, “Throughout our careers, we are taught to conform — to the status quo, to the opinions and behaviors of others, and to information that supports our views.” What’s more, as noted by Psychology Today, this conformity is accelerated in a small group setting — such as a corporate team or enterprise department — and further enhanced, according to Psych Central, by neurotransmitters such as dopamine that are produced when humans are part of a social group.

As a result, when it comes to well-written phishing emails that are purportedly coming from CEOs or HR mangers, staff are preconditioned to reply ASAP with requested information — even if they’ve had previous security training. Social pressure almost invariably trumps learned email security.

It Won’t Happen to Me!

While socially driven email networks increase the likelihood of faux-insider messages getting through the security chain, what about outside attacks? Much time and attention has been devoted to educating employees about the telltale signs of external phishing attempts, such as emails purportedly from financial institutions, government agencies or new business contacts.

Here, another facet of human social interaction is at work: Our natural disposition to believe we’re better than everyone else. It’s called the superiority illusion and, as noted by Scientific American, causes most people to think they’re better than average at most things, such as the ability to spot and prevent phishing attacks.

Since it’s impossible for the majority of people to be above average, the result is that advanced spam and phishing campaigns that make it past initial defenses may get overlooked by overconfident employees who assume they would recognize any sign of these attacks. It’s the old “it won’t happen to me” argument: Users presume they’ve got all the knowledge they need to spot attacks and if they’re victimized, there’s no way anyone could have seen it coming.

Evolve Your Email Security Strategy

What does this mean for companies looking to prevent phishing attacks?

First, there’s no need to ditch current security training. But, as CSO Online pointed out, it’s also a good idea to educate users on how not to craft an email. Don’t be your own worst enemy by sending unexpected, hastily typed emails with “URGENT” in the subject line.

Fundamental shifts in email security, however, require a rethinking of current best practices. To handle social expectation issues, companies must adopt top-down cultural change that prioritizes safety over speed. This is easier said than done when CEOs need hard data for stakeholders or chief financial officers (CFOs) are handling financial fluctuations in real-time, but giving staff time to double-check message origins and intentions before replying goes a long way toward reducing the number of reeled-in employees.

For security professionals, this means developing the ability to present potential phishing losses as line-of-business issues. In practice, this requires leading with context: How are current security issues impacting strategic objectives such as cost savings, customer confidence and regional performance? This can help shore up the notion that time lost to double-checking email requests via phone calls, face-to-face meetings or other methods is preferable to the monetary loss associated with successful attack campaigns.

Dealing with exceptional behavior, meanwhile, starts with a layered email security approach that eliminates obvious phishing attempts before they hit inboxes. Another key component of this defensive strategy is artificial intelligence (AI). AI-based tools capable of analyzing enterprise communication patterns and spotting inconsistencies already exist. Making them applicable to “above-average” phishing finders means leveraging a kind of low-key notification process, in turn aligning with user beliefs about their own ability to recognize phishing attempts.

Address the Human Components of Phishing

Email remains the top enterprise communication method and the obvious choice for attackers looking to compromise business networks. While current email security solutions can help mitigate phishing impacts, companies must recognize the role of corporate email as a social network to address the critical human components of this risk: social expectation and the superiority exception.

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Douglas Bonderud

Freelance Writer

A freelance writer for three years, Doug Bonderud is a Western Canadian with expertise in the fields of technology and...