TL;DR For compliance, most organizations will need at least one pentest annually, but in some cases, more frequent pentesting can be beneficial for finding vulnerabilities and reducing the risk of a breach.
Why Are Regular Pentests Crucial?
Before diving into the pentest frequency, it’s essential to understand the importance of penetration tests. A pentest simulates a real-world attack on your systems and identifies vulnerabilities that could be exploited by cybercriminals. There are a lot of different types of pentests from internal, external, web app, and more. Regular testing helps to mitigate risks, maintain compliance, and provide security awareness within your organization.
Factors Influencing Penetration Testing Frequency
Regulatory and Industry Standards
Finance, healthcare, and other industries mandate specific testing frequencies. For example, PCI DSS compliance requires a pentest at least annually or after significant infrastructure changes. SOC 2 compliance requires organizations to implement security controls across five key “Trust Services Criteria”: Security, Availability, Processing Integrity, Confidentiality, and Privacy; essentially ensuring that customer data is protected through robust security practices, readily accessible when needed, processed accurately, kept confidential, and handled according to privacy regulations, all while documenting and demonstrating the effectiveness of these controls through regular audits. Meeting these criteria may require more frequent testing.
Business Size and Complexity
Small businesses typically require pentests once a year unless they store sensitive data or experience significant changes in their systems. Large enterprises with complex infrastructures may require penetration tests quarterly or even monthly in high-risk environments.
Rate of Change in IT Infrastructure
Businesses undergoing rapid technological change—such as adopting new software, cloud migrations, or mergers—should conduct pentests after every major update or addition.
Cyber Threat Landscape
An increase in targeted attacks or vulnerabilities within your industry might necessitate more frequent testing to stay ahead of potential threats.
Risk Appetite
How detrimental a breach would be to an organization can affect how often a pentest will, or should, be pursued.
Budget and Resources
While frequent testing is ideal, budget constraints often dictate frequency.
Recommended Pentesting Schedules
| Scenario | Frequency |
| Regulatory compliance (e.g., PCI DSS) | Annually or after changes |
| Small businesses with low risk | Annually |
| Large enterprises | Quarterly or monthly vulnerability scans and annual or every six months penetration testing |
| High-change environments | After every major update |
| Post-breach investigation | Immediately after the breach |
Balancing Frequency With Continuous Monitoring
While both are crucial for cybersecurity, “continuous monitoring” focuses on real-time detection of potential threats by constantly analyzing system activity, whereas penetration testing involves periodic, in-depth assessments of vulnerabilities by simulating actual attacks to identify weaknesses in a system.
Continuous monitoring should not be confused with automated pentesting. While automated penetration testing has come a long way, manual pentesting involves a human expert who manually tests systems to uncover complex, custom vulnerabilities that automated tools might miss.
Tailoring Pentesting To Your Needs
There’s no one-size-fits-all answer to how often a business should perform a pentest. The frequency should align with your organization’s risk profile, regulatory requirements, risk appetite, and budget. By staying proactive and integrating pentests into a broader cybersecurity strategy, you can protect your business and maintain customer trust.
If your organization finds itself in need of a pentration test, TCM offers professional pentesting services of various types, from physical to full red team engagements. We aim for open communication in every step of the process and strive to leave you informed and prepared to better secure your organization against cyber attacks.
About TCM Security
TCM Security is a veteran-owned, cybersecurity services and education company founded in Charlotte, NC. Our services division has the mission of protecting people, sensitive data, and systems. With decades of combined experience, thousands of hours of practice, and core values from our time in service, we use our skill set to secure your environment. The TCM Security Academy is an educational platform dedicated to providing affordable, top-notch cybersecurity training to our individual students and corporate clients including both self-paced and instructor-led online courses as well as custom training solutions. We also provide several vendor-agnostic, practical hands-on certification exams to ensure proven job-ready skills to prospective employers.
Pentest Services: https://tcm-sec.com/our-services/
Follow Us: Email List | LinkedIn | YouTube | Twitter | Facebook | Instagram | TikTok
Contact Us: [email protected]
See How We Can Secure Your Assets
Let’s talk about how TCM Security can solve your cybersecurity needs. Give us a call, send us an e-mail, or fill out the contact form below to get started.