When it comes to cybersecurity, it’s not the high-profile attacks that keep professionals awake at night. Instead, it’s often overlooked vulnerabilities—like an open RDP port left exposed during a quick test months ago or a domain admin password that hasn’t been updated in decades. These overlooked issues can create massive security risks for organizations.
In a recent discussion with Braden Bailes, co-founder of Soma Cyber, we explored the world of penetration testing (pen testing) and what businesses often miss in their security practices. The insights shared aren’t just technical; they challenge the way companies should approach their entire security posture.
Why Penetration Testing is More Important Than Ever
Cybersecurity has become increasingly complex. Gone are the days when networks were simple and flat—today’s IT environments include cloud services, IoT devices, isolated networks, and AI-driven systems. As a result, traditional security measures no longer cut it.
Penetration testing goes far beyond basic vulnerability scanning. It’s about simulating real-world attacks to identify weaknesses that automated tools might overlook. This process helps uncover misconfigurations, forgotten protocols, and human errors that can create major security gaps.
As networks grow more complicated, the number of potential entry points increases, making thorough penetration testing an essential part of modern security practices.
The Startling Reality: 90% of Breaches Begin the Same Way
The harsh reality of most cyberattacks is that they don’t start with a complex, zero-day exploit. In fact, the majority begin with a simple method: a phishing email.
While organizations often invest heavily in firewalls and intrusion detection systems, attackers are more likely to send a convincing email with a malicious link or attachment. Whether disguised as an invoice or an urgent document, it only takes one click for an attacker to gain access.
Once they’ve breached the system, the attack unfolds quickly:
- Persistence: Attackers establish ways to maintain access.
- Privilege Escalation: They attempt to gain higher-level permissions.
- Lateral Movement: The attacker spreads through the network to access valuable data.
- Data Exfiltration: Ultimately, the attacker will steal sensitive information.
This is why employee security training is so critical. It’s the first and often most effective line of defense against these types of attacks.
Understanding the Attacker’s Mindset
What sets successful security teams apart is their ability to think like attackers. Rather than being reactive, they proactively anticipate how attackers might exploit weaknesses in the system.
Adopting the attacker’s perspective helps improve detection systems, adjust configurations, and deploy stronger defenses. Penetration testing is invaluable in this respect. Pen testers simulate an attacker’s approach, offering a fresh and objective view of your security systems.
Red Team, Blue Team, and Penetration Testing: Key Differences
There’s often confusion around the various types of security assessments. Here’s a breakdown:
- Penetration Testing: This is a broad, in-depth test focused on identifying as many vulnerabilities as possible. It’s intentionally noisy and comprehensive, offering actionable intelligence on your security weaknesses.
- Red Team: This type of testing mimics real-world attacker behavior in a more stealthy and long-term manner, often testing your organization’s detection and response capabilities.
- Blue Team: These are the internal security teams responsible for monitoring systems, responding to threats, and maintaining security on a daily basis.
Knowing the distinctions between these testing types helps companies choose the best option based on their needs.
Common Security Gaps That Penetration Testers Keep Finding
After years of testing, certain vulnerabilities repeatedly surface. These are often not sophisticated attacks but rather basic misconfigurations that organizations overlook:
- Default Configurations: Leaving systems with factory default settings or failing to harden security protocols can create easy entry points for attackers.
- Legacy Settings: Outdated configurations from older software versions that weren’t updated during system upgrades often leave large security holes.
- Excessive Permissions: Granting unnecessary access to user accounts or using service accounts with admin privileges weakens security. Implementing the principle of least privilege is crucial.
- Forgotten Access Points: Open ports, databases, and temporary access points that were never properly closed or removed provide attackers with easy entry points.
The Value of External Penetration Testers
Internal teams often suffer from what’s known as “blue team cognitive bias.” When you work with the same systems daily, certain vulnerabilities or assumptions can go unnoticed. External penetration testers bring fresh eyes and valuable experience from working on a wide range of networks. They don’t have preconceived notions about how your environment should operate, allowing them to spot issues that might have been overlooked by your internal team.
Cultivating a Security-First Culture
The most secure organizations aren’t always the ones with the most advanced technology. They share common traits:
- Transparency: These organizations acknowledge that they have security gaps and want to identify them before attackers do. Leadership views findings as opportunities to improve rather than personal failures.
- Ongoing Training: Security isn’t a one-time initiative. Employees—from developers to system admins—receive continuous education on emerging threats and best practices.
- Embracing Testing: Just like physical fitness, security requires regular “exercise.” Penetration testing isn’t about passing or failing; it’s about building resilience and improving over time.
- Collaborative Security: Strong security partners, such as auditors and pen testing firms, are seen as collaborators rather than adversaries.
Real-World Lessons Learned
Penetration testing isn’t just theoretical—real-world examples highlight the risks of small oversights. For instance, a hospital system with thousands of user accounts suffered a complete compromise of its Active Directory due to a single outdated setting. In another case, a food distributor’s “test” database, which contained a full copy of production data, was left wide open, allowing attackers to access sensitive information.
These examples show that even minor oversights can lead to catastrophic security breaches. Regular testing helps organizations identify these vulnerabilities before attackers do.
Preparing for Penetration Testing
If you’re planning a penetration test, preparation is key:
- Involve your IT team: Designate a primary contact for critical findings and ensure the broader team understands the testing process.
- Identify your most critical assets: Determine what systems or data would cause the most harm if compromised.
- Set clear objectives: Whether you’re testing incident response, looking for specific vulnerabilities, or assessing overall security, clear goals lead to more valuable insights.
- Prepare mentally: Penetration testing is about learning and improving. Findings should be seen as opportunities to strengthen your defenses, not as attacks on competence.
Looking Ahead: The Future of Cybersecurity
As technology continues to evolve, the need for thorough security testing will only increase. The expanding attack surface presents both challenges and opportunities for defenders. The organizations that thrive will be those that make penetration testing an ongoing process, invest in continuous training, and embrace security testing as a fundamental part of their culture.
Remember, attackers only need to be right once, but your defenses need to withstand every potential attack. Make your security as difficult as possible for attackers to navigate, and regularly test your defenses to stay one step ahead.
