Ever wondered what actually keeps cybersecurity professionals up at night? It's not the sophisticated nation-state attacks making headlines, it's the forgotten RDP port left open from a "quick test" six months ago or the domain admin password that hasn't been changed since 1998.
In a recent Miller Mindset episode, we explored the real world of penetration testing with seasoned red teamer Braden Bailes, co-founder of Soma Cyber. What emerged wasn't just technical insight, but a fundamental shift in how organizations should think about their security posture.
The cybersecurity landscape has exploded in complexity. Gone are the days of flat networks where "if you're on the network, you can access everything." Today's IT environments are a maze of cloud services, IoT devices, segregated networks, and increasingly, AI-integrated systems.
Penetration testing isn't just vulnerability scanning with a fancy name. Real pen testing goes deep, simulating how an actual attacker would navigate your defenses. It's about finding the holes that automated tools miss, the misconfigurations, forgotten protocols, and human elements that create the biggest security gaps.
The complexity of modern networks means more attack surfaces, potential entry points, and ways for things to go wrong. That's exactly why thorough penetration testing has become essential, not optional.
Here's the uncomfortable truth about most cyberattacks: they don't begin with some exotic zero-day exploit. Nine out of ten breaches start with something embarrassingly simple—a phishing email.
Think about it: while IT teams spend thousands on firewalls and intrusion detection systems, attackers are often just sending a convincing email with a malicious Excel file. Maybe it's disguised as an invoice from a vendor, or an urgent document from the finance department. One click, and suddenly there's a foothold in your network.
Once that initial access is gained, the attack chain moves fast:
This is why security training isn't just a checkbox, it's your first and often the most critical line of defense.
What separates effective cybersecurity teams from those constantly playing catch-up? They put themselves in the mind of the attacker.
Understanding the attacker mindset isn't about becoming paranoid, it's about staying ahead of evolving tactics, techniques, and procedures (TTPs). When you can anticipate how an attacker might approach your systems, you can fine-tune your detection systems, adjust your SIEM configurations, and deploy more effective defenses.
The real value of penetration testing lies in this perspective shift. A skilled pen tester brings the outsider's view. They don't know your network, your workarounds, or your "that's always been that way" assumptions. They see your environment the way an actual attacker would.
There's often confusion about the different types of security testing. Here's what distinguishes them:
Penetration Testing is intentionally noisy and comprehensive. The goal is to find as many vulnerabilities as possible and provide actionable intelligence. Pen testers aren't trying to be covert, they're conducting a thorough security assessment.
Red Team engagements are more about stealth and realism. They simulate actual attacker behavior, often over longer periods to test detection and response capabilities.
Blue Team refers to your internal security defenders, the people monitoring systems, responding to alerts, and maintaining your security posture day-to-day.
Understanding these distinctions helps organizations choose the right type of assessment for their needs and set appropriate expectations.
After years in the field, certain vulnerabilities show up again and again. These aren't sophisticated exploits, they're basic misconfigurations that organizations consistently overlook:
Active Directory defaults that were never hardened, AWS settings left at factory defaults, or network protocols that should have been disabled years ago. These represent some of the easiest wins for attackers.
Remember that university with 30,000 students and domain admin passwords unchanged since 1998? If you don’t remember, you can hear about it in this Miller Mindset episode.Legacy configurations from earlier, less secure versions of software often persist through upgrades, creating massive security holes.
User accounts with far more access than necessary, service accounts with admin privileges, or network shares accessible to everyone. The principle of least privilege isn't just best practice,it's essential.
That RDP port opened for "quick testing" and never closed. The development database that's actually a full copy of production data. The VPN access that was supposed to be temporary. These forgotten entry points are gold mines for attackers.
Internal teams suffer from what's called "blue team cognitive bias." When you work with the same systems every day, certain assumptions become invisible. That alert that never means anything important might be the one that matters. That "secure" configuration might have a flaw you've never considered.
External penetration testers bring something invaluable: fresh eyes and experience across hundreds of different networks. They don't have preconceptions about how things "should" work in your environment. They see your network the way an attacker would as a target to be understood and exploited.
This outside perspective often reveals vulnerabilities that have been hiding in plain sight, sometimes for years.
The strongest security environments share common characteristics, and technical sophistication isn't necessarily at the top of the list. The most secure organizations are those that:
Embrace transparency. They know they have problems and want to find them before attackers do. Leadership doesn't take security findings personally, they see them as opportunities to improve.
Invest in training. From developers to system administrators, everyone understands their role in maintaining security. This isn't one-time training, it's ongoing education about evolving threats and best practices.
View testing as strength building. Just like physical fitness, security requires regular exercise. Penetration testing isn't a pass/fail exam, it's a workout that builds organizational resilience.
Maintain good relationships with security partners. Whether it's auditors, managed security service providers, or pen testing firms, adversarial relationships help no one. The goal is collaborative improvement, not defensive posturing.
Some of the most valuable insights come from actual penetration testing experiences. Consider the hospital system with 8,000 user accounts that suffered complete Active Directory compromise due to a single legacy setting and one admin mistake. Or the food distributor whose "test" database contained a full copy of production data, wide open to anyone who found it.
These aren't theoretical vulnerabilities, they're real-world examples of how small oversights can create massive security holes. The lesson isn't that these organizations were incompetent, but that complexity creates blind spots, and regular testing helps identify them.
If you're planning a penetration test, preparation makes all the difference:
Get the whole IT team involved. Designate a primary contact who can respond quickly to critical findings, but ensure the broader team understands what's happening and why.
Identify your critical assets. What systems, data, or processes would hurt most if compromised? Make sure your pen testing firm understands these priorities.
Define clear objectives. Are you testing incident response times? Looking for specific vulnerabilities? Assessing overall security posture? Clear goals lead to more valuable results.
Prepare mentally. This isn't about passing or failing, it's about learning and improving. Findings aren't personal attacks on your competence; they're opportunities to strengthen your defenses.
As technology continues evolving with AI integration, expanded IoT deployments, and increasingly complex cloud architectures the need for thorough security testing will only grow. The attack surface is expanding, but so are the tools and techniques for defending it.
The organizations that thrive will be those that embrace testing as a continuous process, not a one-time event. They'll invest in training, maintain strong relationships with security partners, and view every finding as a chance to get stronger.
Remember: the attacker only needs to be right once, but they have to successfully navigate every defense you've put in place. That's not the defender's dilemma, that's the attacker's challenge. Your job is to make that challenge as difficult as possible.
🎥 Watch the Full Episode: Miller Mindset→
This insight comes from a recent Miller Mindset episode featuring penetration testing expert Braden Bailes. For the full conversation about attacker mindset, common misconfigurations, and building better defenses, check out the complete episode.