Security Without Pessimism: Shadow IT – When Convenience Becomes a Security Risk

The Shortcut That Became the Standard

We’ve all done it.

You’re trying to get something simple done, but the company’s “official” tool takes six steps and two approvals just to open a project. So, you find a better one, quicker, cleaner, easier.

Maybe it’s a shared Google Sheet, a new messaging app, or some AI productivity tool that actually works. It saves you time, gets results, and honestly, no one seems to mind.

That is, until someone finally notices.

That’s Shadow IT, the silent, well-intentioned workaround that slowly turns into a security liability.

The issue isn’t carelessness; it’s the drive for efficiency.

The Anatomy of Shadow IT and How It Slips Through

Shadow IT doesn’t begin as an act of rebellion. It starts as a way to get things done.

Teams feel pressure, tools are slow, and company processes can’t keep up. So, someone tries a new tool that bends the rules, just for this one time.

That quick fix gets shared with others and soon becomes the usual way of doing this.

Before long, company data is moving through several tools that no one has officially approved:

  • Free cloud drives with no encryption.
  • Personal accounts are used for client data.
  • Messaging platforms without audit trails.
  • Chrome extensions quietly sync user info to external servers.

It’s not done out of malice; it’s just human nature. People pick what helps them get the job done. But each time we choose convenience over control, we lose sight of what’s happening.

Why Good People Go Rogue

Most shadow IT isn’t about breaking rules. It’s about finding better ways to work.

People want to do their jobs well. When approved systems slow them down, they look for alternatives. This creativity isn’t careless, but it can still be risky.

Most people don’t focus on compliance when facing a tight deadline. They focus on getting results.

Here’s the problem: attackers know this. They rely on busy teams taking shortcuts, creating unmonitored accounts, or storing data in places that go unnoticed.

Shadow IT doesn’t look like rule-breaking. It looks like taking initiative.

When Visibility Vanishes

Each unapproved app creates another potential risk.

Security teams can’t track data, fix vulnerabilities, or control access. Soon, they may not even know what needs protection.

If something goes wrong, you can’t protect what you can’t see. A hacked third-party app or a compromised account can quietly put the whole system at risk.

Shadow IT isn’t a single big mistake. It’s many small, hidden problems. By the time someone notices, it’s often too late to trace the cause.

Balance Control with Capability

The solution isn’t to make things stricter. It’s to make official tools easier to use.

Security should support people in their actual work, not just follow what policy says.

Here’s what helps:

  • Simplify the approved stack. If it’s painful to use, it’s already compromised.
  • Create a “request to innovate” process. Let employees suggest tools safely.
  • Shadow IT discovery audits. Not witch hunts — open conversations.
  • Default to transparency. Make it normal to say, “I’m testing this app” without fear.

The aim is partnership, not strict control. If security punishes creativity, people will just hide what they’re doing. Problems will still find a way through.

Building Trust Around Tools

You can’t get rid of Shadow IT by being strict. The only way is to build trust instead of secrecy.

If people think speaking up will get them in trouble, they’ll stay silent. But if they see it as a chance to work together, you’ll know what’s really happening.

The best workplaces see curiosity as a strength, not a risk. Security and innovation aren’t enemies; they work together toward the same goal.

Final Thought

Shadow IT isn’t caused by bad people. It happens when good intentions don’t fit with strict systems. For security to keep up with creativity, it needs to act as a guide, not just a gatekeeper.

That’s not being pessimistic. That’s reality and an opportunity to get better, together.

The Art of Cyberwar | Part III | Attack by Stratagem

The principle:
If you know the enemy and know yourself, you need not fear the result of a hundred battles.  Sun Tzu – Chapter III

the golden era

Strategy vs. Stratagem

A strategy is designed for longevity, while a stratagem addresses immediate challenges. Strategy anticipates years ahead to foster resilience. Stratagem focuses on the next breach, exploit, or distraction.

Within cybersecurity, strategy encompasses architectural design, layered controls, validated incident response plans, and a culture prepared to act decisively during crises. Stratagem represents the attacker’s tools, such as persuasive emails, covert code injections, or precisely timed physical penetration tests.

Both approaches are powerful, yet each possesses inherent limitations.

The Modern Battlefield: Fluid and Fractured

The threat landscape evolves continuously. Traditional boundaries are replaced by cloud environments, API vulnerabilities, and interconnected third-party networks. Security architects must prioritize adaptability and fluidity over static defenses to effectively mitigate risks.

Zero Trust principles, continuous validation, and integrated security practices throughout the development lifecycle enable proactive identification and mitigation of vulnerabilities prior to production deployment. In an environment where compromise is presumed and rapid response is critical, these measures are indispensable.

Effective defenders adopt a proactive stance. They anticipate adversary actions, analyze behavioral patterns, and design systems to adapt under attack rather than fail.

Attack by Stratagem: The Psychology of Exploitation

Major breaches often originate through psychological manipulation rather than technical flaws. Techniques such as phishing, vishing, and deepfakes exploit cognitive vulnerabilities to diminish user awareness. This approach mirrors historical propaganda methods, where controlling perception leads to controlling behavior.

While governments previously leveraged headlines and radio broadcasts, contemporary attackers exploit digital interfaces such as login pages and hyperlinks. Both strategies depend on user fatigue, habitual behavior, and misplaced trust. If users believe a fraudulent login page is legitimate, they inadvertently compromise security.

Similarly, if citizens equate fear with patriotism, they may relinquish critical judgment in favor of perceived safety. As Ben Franklin observed, individuals who prioritize temporary safety over essential liberty may ultimately forfeit both: “Those who would give up essential Liberty, to purchase a little temporary Safety, deserve neither Liberty nor Safety.

This tactic operates effectively across a spectrum, from individual email inboxes to broader ideological movements.

The Architecture of Awareness

A resilient security architecture reflects the characteristics of an aware and vigilant mindset.

Network segmentation limits the blast radius. Application hardening predicts misuse before it happens.

Firewalls and Security Information and Event Management (SIEM) systems provide the critical, irreplaceable resource of time.

Knowing your environment is knowing yourself.

Without a thorough understanding of all dependencies, exposures, and behavioral patterns, it is impossible to detect significant changes or anomalies. The same principle applies at the national level: when societies cease to critically evaluate their narratives, division and deception proliferate with ease.

Propaganda Built Into the Code

James Montgomery Flagg, I Want You for U.S. Army, 1917, collection of Chip and Carrie Robertson, photo by Robert Wedemeyer
James Montgomery Flagg, I Want You for U.S. Army, 1917, collection of Chip and Carrie Robertson, photo by Robert Wedemeyer

From Woodrow Wilson’s Committee on Public Information to the televised theater of Desert Storm, America learned how framing shapes belief.

Attackers apply similar principles, constructing their deceptive tactics by exploiting established trust.

Deceptive login pages replicate corporate portals, ransomware communications adopt professional language, and deepfakes are crafted to appear and sound authentic.

The primary threat is not the attack itself, but the absence of awareness regarding potential dangers. Stratagem prevails when critical scrutiny is abandoned.

Reverse Engineering the Present

Post-incident analyses consistently reveal that warning signals were present before breaches. Although alerts, logs, and telemetry data were available, they did not translate into actionable understanding.

Visibility does not equate to genuine situational awareness.

Historical events reinforce this observation.

The United States has engaged in conflicts based on incomplete or inaccurate information, often mistaking perception for certainty.

In both cybersecurity and geopolitics, failure frequently results from conflating raw data with meaningful insight.

Understanding adversaries requires effective intelligence gathering, including threat hunting, reconnaissance, and red-team exercises.

Self-awareness in cybersecurity necessitates discipline, such as maintaining asset visibility, ensuring policy integrity, and sustaining composure during operations.

A deficiency in either area enables adversarial stratagems to succeed.

The Quiet Defense

The most robust networks, analogous to resilient individuals, operate discreetly.
They do not engage in ostentatious displays; instead, they maintain a constant state of preparedness.

Their resilience is embedded within their structural design rather than expressed through rhetoric.

Authentic resilience does not stem from more active dashboards or faster technical tools. Resilience is rooted in organizational culture, situational awareness, and a humble approach. It is defined by the ability to learn, adapt, and respond more rapidly than emerging threats.

Cybersecurity, akin to statecraft, is a continuous endeavor to prevent breaches. Success is achieved not by engaging in every conflict, but by anticipating and neutralizing threats before they materialize, thereby securing victory without ever having to fight. Bringing us full circle back to understanding the fundamental nature of the original principle: If you know the enemy and know yourself, you need not fear the result of a hundred battles.

Multi-Factor Authentication: Boring, Annoying, Essential

In cybersecurity, we get excited about new technologies like AI, zero trust, and quantum encryption. But ask any practitioner what quietly stops the most breaches day to day? It’s still MFA.

Multi-Factor Authentication may not be exciting. It can slow people down and sometimes feels awkward. Even so, it remains one of the best ways to stop credential theft, which is the most common way attackers get into any network.

Why MFA Matters

• Passwords are weak. People reuse them across accounts, attackers buy them on the dark web, and “123456” still shows up in breach data.
• Phishing is effective. Users still click links and enter credentials. MFA blocks stolen passwords from being enough.
• Attacks are automated. Bots hammer login pages at scale. MFA breaks that automation by forcing a second factor.

Despite everything we know, MFA is still the easiest and most effective step in cyber defense. It often makes the difference between stopping an incident and having to respond to one.

The Pushback Problem

When we first rolled out MFA our district, the resistance was loud.

“It’s annoying.”
“It slows us down.”
“We don’t have time for that.”
“Why do I need this if I’m just checking email?”

At first, security changes can feel like a big hassle for everyone, whether you’re a teacher, technician, or leader. But a few seconds of extra effort can save us from days or even weeks of problems.

To make sure everyone accepted MFA, we took our time and built support step by step:

• Continuous staff education. Regular updates explained the “why” behind MFA, not just the “how.”
• Knowledge-base articles gave our help desk a clear playbook, no scrambling when someone was locked out or confused.
• Anticipating questions became part of the rollout strategy. From custodians logging into shared workstations to the superintendent approving district-wide communications, everyone got personalized guidance.

We kept the message clear: MFA is not a burden. It’s part of how we protect our entire staff and precious student PII, and PHI data. We aways have to remain FERPA, COPPA, CIPA, and PPRA compliant.

Over time, the complaints faded. Now, using MFA is second nature. It’s simply part of our routine.

The Fix

• Enforce MFA on all critical systems.
• Use phishing-resistant methods (authenticator apps, hardware keys) and worst-case scenario SMS.
• Train users that a few extra seconds of friction is the cost of resilience.

The Parallel

Using MFA is similar to wrapping your hands before boxing. It might seem tedious when you’re just getting started, but it protects you. If you skip it once, you might be fine, but skip it again, and you risk real trouble.

Security, like weightlifting, CrossFit, martial arts or meal prep it works best when the basics become instinct.

Again, MFA is boring. But, it’s also one of the most powerful shields you have.