Everything an IT pro needs to know about penetration testing
The vast majority of IT professionals will agree that in cybersecurity, waiting for an attack to happen in order to expose weaknesses is a losing strategy.
As such, many will be well-clued up on the benefits of penetration testing; from demonstrating a commitment to protecting sensitive data and ensuring ongoing compliance with industry regulations, to gaining a clearer understanding of security gaps, and strengthening incident response readiness.
But if and when organizations should progress from simply relying on vendors and meeting basic compliance requirements to embracing frequent, proactive pen testing is much more of a grey area.
Every business should strive to reach the highest level of maturity. However, from my experience in the field, businesses typically fall at different points along a cybersecurity maturity model, with each stage requiring a different level of pen testing:
Level 1: A business that’s invested in multiple cybersecurity products
Here, an organization does no pen testing, but has acquired multiple security tools, like a firewall, endpoint security solution, or SIEM platform. However, even when installing a top-tier security product, this product will only be as effective as its implementation and ongoing maintenance. If it’s not configured correctly, regularly updated, fully utilized, or even left with default settings, vulnerabilities can slip through unnoticed. For companies operating on this level - which we’d hope are few and far between - I’d remind them that security is a process, not a purchase and that there are clear downsides when avoiding testing altogether.
Level 2: A business that demonstrates regulatory compliance, adopts passive vulnerability scanning, and pen tests annually
Next, we have companies that realize they must demonstrate regulatory compliance, especially those in finance, healthcare, or retail, so they start ticking the boxes for PCI-DSS, HIPAA, or ISO 27001. Compliance often mandates vulnerability scans, so organizations at this level usually run automated tools to check for known security issues. These scans adopt an “outside-in” perspective, spotting open ports, weak passwords, or unpatched systems, but often don’t demonstrate their exploitability or combined impact, meaning it remains a passive exercise.
Here, organizations also begin to use pen tests, typically to meet a specific compliance requirement or to confirm the findings of their vulnerability scans. These engagements may happen once or twice a year, offering a deeper “snapshot” of security at that moment, yet the limited scope and frequency can leave long intervals where new vulnerabilities slip by unnoticed.
It’s a solid improvement on level one and standards are of course critical for establishing baseline security controls, but attackers don’t care about certifications, they care if you have any exploitable weaknesses. And unfortunately, compliance standards aren’t designed to handle evolving cyber threats. Scanners can miss complex exploit chains that combine multiple minor flaws, and given the rapid pace of software updates and the daily discovery of new exploits, an annual or semi-annual test can’t keep up with the emerging threats.
Level 3: A business that champions proactive, frequent testing and PTaaS
Finally, we have companies - often very forward-thinking and proactive in their approach to cybersecurity - that are highly aware of the fact that the average cost of a data breach can run into millions, especially when you factor in legal fees, fines, and reputational damage. With this in mind, these firms realize that static or infrequent testing leaves major gaps in their defenses and therefore schedule multiple pen tests throughout the year. Here, often via Penetration Testing as a Service (PTaaS), they will mix external (outside-in) and internal (inside-out) approaches, and prioritize the remediation of findings. They also track “mean time to detect” and “mean time to remediate,” actively measuring how quickly their team responds to simulated breaches.
The following snapshot of what PTaaS typically offers is helpful to look at here:
- Internal & External Network Testing
- Multiple internal IPs, external IPs, and servers.
- Targets vulnerabilities from both insider threats and external actors.
- Website Assessments
- Coverage for websites, scanning for weak configurations, SQL injection points, and cross-site scripting (XSS) flaws.
- External Web Application Testing
- Black Box approach, focusing on runtime exploitation.
- Supports login systems, API inputs, functions, and roles.
- Utilizes tools like BurpSuite, manual scripts, and custom exploits.
- No code review included, meaning it simulates an attacker’s view of the app.
Taking this approach ultimately reduces the window for vulnerabilities to remain unaddressed, and hence lowers the risk and potential cost of a real breach. In fact, according to industry estimates, organizations that practice continuous penetration testing are over 40 percent more resistant to cyber attacks than organizations that rely on point-in-time security tests.. In contrast, organizations that remain at the compliance-only stage tend to detect breaches only after significant (and often expensive) damage is done.
Which level should my business be on?
While many smaller organizations may believe levels 1 or 2 may suffice, leaving level 3 for the larger businesses with annual revenues in the millions, the reality is somewhat different.
The attack surface for cybercriminals has widened dramatically and cybersecurity risks are no longer confined to large businesses; roughly 43 percent of cyberattacks focus on small businesses, mainly because these companies often lack advanced defenses. At the same time, public sector entities and critical infrastructure, including government, healthcare, and education, have all been increasingly targeted by ransomware campaigns. With attackers using AI-driven reconnaissance tools, they can discover unpatched services or weak credentials at scale, regardless of an organization’s size.
The bottom line is, that if you’re online, you’re a target, and while compliance checklists, vendor contracts, and occasional scans form necessary checkpoints on the cybersecurity journey, they’re only stepping stones.
As cybercriminals harness AI and automation, your organization needs agile, frequent, and in-depth methods to uncover hidden vulnerabilities. This is exactly why PTaaS can be a game-changer for companies seeking robust defenses against increasingly sophisticated adversaries.
Image Credit: Putilich / Dreamstime.com
Rajeev Gupta is Co-founder & Chief Product Officer, Cowbell, offers a deep dive into the world of penetration testing; from how often to test and compliance requirements to the benefits of PTaaS vs traditional testing.