The cyber threat landscape is not just growing, it is mutating. Modern cyberattacks, supercharged by the power of generative AI, now operate at a scale, speed, and sophistication never seen before. The threat landscape has escalated from periodic alerts to a nearly continuous state of attack. Hackers today no longer wait for an opportunity, they create them.
Cyber criminals are using AI tools to automate reconnaissance, exploit zero-day vulnerabilities, and even analyze an organization’s defenses. They then adapt attack methods to exploit vulnerabilities. Cyberattacks are not just faster, they are smarter. According to a report published in 2025, 50% of vulnerabilities identified in the past 12 months did not exist before.
That’s why penetration testing is no longer optional, it’s a strategic investment. Studies show that for every $1 spent on testing, organizations save up to $10 in breach-related costs.
The Old Way of Penetration Testing is Broken
Traditionally, penetration testing has been considered a once-a-year checkbox activity—an exercise in compliance, not resilience. A survey conducted during a recent ACA webcast, Anticipating the Attack: Reducing the Risk of Cyber Breaches with Penetration Testing, revealed that more than 58% of attendees conduct penetration testing once a year or on an ad-hoc basis. This approach may satisfy regulators, but it fails to address the dynamic and persistent nature of today’s threats. Even worse, many firms only test a narrow slice of their environment—such as external networks—while leaving other critical parts of their IT infrastructure—like the internal network, wireless network, or their cloud infrastructure—untested. These blind spots create hidden vulnerabilities attackers can easily exploit.
Fortunately, that mindset is evolving.
More organizations, especially in highly targeted sectors like financial services, are conducting penetration testing regularly. They are recognizing that being ‘secure last quarter’ means little when new attack vectors emerge weekly. According to a report, one midsized firm that moved from testing annually to quarterly reduced unresolved vulnerabilities by 42% within six months.
Regular, ongoing testing helps keep organizations secure and ready to handle new threats. Beyond security, frequent penetration testing also sends a strong message to stakeholders and regulators about a firm’s commitment to cybersecurity, turning technical due diligence into a strategic advantage.
What is Penetration Testing (and What It Isn’t)
Penetration testing is a controlled, ethical simulation of a cyberattack conducted by security experts to identify and exploit vulnerabilities across an organization’s systems, networks, and applications. Pen testers actively attempt to break into an organization’s systems using real-world tactics to show how attackers could gain unauthorized access, move laterally across networks, or steal sensitive data. It’s not enough to identify security gaps—penetration testing shows how they can be exploited and how to eliminate those gaps.
Vulnerability scanning and penetration testing are often used interchangeably. However, they serve very different purposes. Vulnerability scanning is an automated process that detects known weaknesses across an organization’s networks and systems. Penetration testing can expose unknown weaknesses, typically a manual approach that attempts to exploit those vulnerabilities to determine their real-world impact.
In short, vulnerability scans and penetration tests are not an either-or proposition. Combining both is crucial to effectively mitigate the risks of a cyberattack.
Mapping The Attack Surface: What Should Be Tested
To operate in today’s digital world, organizations rely on a complex mix of cloud platforms, custom applications, internal networks, wireless setups, and third-party integrations. These tools drive efficiency and innovation, but they also significantly expand the attack surface.
Each part of an organization’s IT infrastructure introduces unique risks and presents opportunities to different types of attackers. While an external hacker may try to breach your firewall, a malicious employee or a misconfigured cloud service could quietly open a back door for exploitation.
That’s why penetration testing needs to be tailored and comprehensive, targeting all key layers of an organization’s digital ecosystem.
Attack Surface Within an IT Infrastructure
- External Network: Includes public facing assets like VPNs, IP addresses, and firewalls.
- Internal Network: Internal environment that can be vulnerable to threats from insiders.
- Web Applications: Includes public or internal portals, APIs, or e-commerce sites.
- Wireless Network: Includes wi-fi, access points, and encryptions.
- Cloud Infrastructure: Includes cloud platforms like AWS, Azure, and Google Cloud, among others.
Penetration tests are highly flexible and can be customized to meet specific focus areas and needs of an organization.
Choosing The Right Approach: Black, White or Grey Box Testing
Different parts of an organization’s IT ecosystem expose the organization to different kinds of threats. A public-facing web app might be attacked by a botnet scraping for injection flaws, while a misconfigured internal network could be exploited by an insider or through lateral movement after an initial breach.
Because each layer has its own risk profile, the testing methodologies must be equally varied, tailored, and strategic. That’s where the concepts of black box, white box, and grey box testing come in.
- Black Box Testing: Testers have little to no prior knowledge of the target systems, just like an external attacker. This simulates real-world hacking attempts and is ideal for assessing the security of public-facing assets like websites, firewalls, and exposed networks.
- White Box Testing: Testers are given full access to internal documentation, configurations, source code, and credentials. This approach provides the most comprehensive view of vulnerabilities across systems, enabling deep analysis of IT infrastructure security.
- Grey Box Testing: A middle ground between black and white box. Testers have partial knowledge — such as limited credentials or architectural insight — simulating the actions of a malicious insider or an attacker who has breached some initial defenses.
A Practical Penetration Testing Roadmap
Continuous risk demands constant validation. This timeline outlines how to structure penetration testing across the year to match the pace of modern threats.
- Event-Driven Penetration Test: Conduct tests triggered by major changes like deployments, cloud moves, merger and acquisitions or compliance needs.
- Monthly/Weekly Continuous Penetration Test: Regularly identify common, easy-to-exploit vulnerabilities through automated tools.
- Quarterly Target Penetration Test: Focus on testing recently added or high-risk assets and verify fixes from previous tests.
- Bi-Annual Full Scope Penetration Test: Establish a comprehensive security baseline covering all critical systems, apps, and user access.
- Annual Red Team Exercise: Emulate real attacker tactics to evaluate detection, response and overall security readiness.
Conclusion
Your organization’s IT infrastructure is only as secure as its weakest link. As cyberattacks evolve, so must your defenses. Regular penetration testing ensures your team catches and addresses new risks early. Moreover, conducting frequent penetration tests demonstrates your firm’s commitment to cybersecurity, reassuring stakeholders and meeting regulatory requirements.
Take the Next Step
Let ACA help you conduct penetration testing and vulnerability assessments to identify network vulnerabilities that can help reduce the risk of a breach and associated financial, operational, and reputational losses. Our penetration testing provides:
- Independent testing from industry experts
- A team with advanced certifications including OCSP, CISSP, CEH, and OSCE3 ensuring the deep technical expertise needed to identify and test vulnerabilities
- Actionable insights to help you reduce risk across your environment
Reach out to your ACA consultant or contact us here to learn how we can improve your cybersecurity posture.