How Often Should Penetration Testing Be Done?

Offensive Security Academy is an educational blog series on offensive security tactics and techniques in the age of AI.

The ideal frequency of penetration testing will be different for every organization. The decision is affected by factors like the size and complexity of the environment, how fast moving it is, whether it manages critical or sensitive data, or if it is in a highly regulated industry. 

Perhaps the most critical factor is a relatively new one — and that is the dramatically increased pace of both software development and cyberattacking. As AI ramps up the pace and capabilities of software development, cyberattacks, and cyber defenses, many traditional cybersecurity best practices, including pen testing frequency, are evolving.

Key takeaways:

• Penetration testing frequency depends on an organization’s size, complexity, and rate of change.

• The nature of the data an organization manages and the regulations it is subject to also play a role in determining rate of pen testing.

• AI is changing traditional thinking on pen testing frequency. 

• The pace of AI-driven software development and cyberattacks makes traditional pen testing frequency recommendations obsolete.

• AI-driven pen testing makes continual offensive testing possible and enables pen testing to keep up with modern software development and attack methods.
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Factors that affect penetration testing frequency

Determining how often penetration tests should be conducted depends on an organization’s compliance requirements, size, complexity, and risk factors. Pen test frequency is also dramatically affected by AI and its impact on the speed of both software development and cyberattacks.

How AI is changing penetration testing frequency

AI is both requiring more frequent pen testing, and making more frequent pen testing possible.

With AI in the mix, more regular pen testing is required because:

• Cyberattackers are leveraging AI to work and adapt faster. The cyberattacker barrier to entry has dropped significantly, meaning attackers can spin up attacks at a pace never seen before, and quickly pivot to new attack methods when something doesn’t work. Your pen test report that verifies the security your assets and systems is now obsolete in days, even hours, after it is published.

• Software developers are leveraging AI to work and adapt faster, and software releases that used to take weeks or months are now taking hours. AI-led software development means the “significant changes” in your environment signaling time for a new pen test are happening daily, even hourly. A point-in-time security assessment is meaningless in a system this dynamic.

At the same time, frequent pen testing is now possible and affordable through AI-driven pen testing, which makes this form of offensive security:

• Faster: Traditional, human-led pen testing typically takes several months to generate a report. AI-assisted pen testing reports are generated in days. By gathering and correlating data, scanning for vulnerabilities, and generating reports at speeds a human pen tester could never reach, AI-driven pen testing is changing the game.

• Less expensive: Traditional pen testing can cost up to $30K per test, making it prohibitively expensive to conduct these tests frequently. AI-driven pen testing costs far less, making frequent or continual testing a financially viable option.
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How size and speed affect pen testing frequency

Most standard guidance on pen testing recommends a test after a major change — an acquisition, product release, or significant software update. If your organization is fast-moving and updating or changing frequently, it follows that more frequent pen tests will be required to ensure any new or updated components are secure.

In addition, larger, more distributed organizations have a more expansive attack surface and higher risk of breach, requiring more frequent pen tests to assess security controls and reduce risk.

Pen testing frequency required by regulations like PCI-DSS and HIPAA

Any organization that is managing sensitive or critical data, like those in healthcare or financial services, should be pen testing more frequently than others. Organizations in these industries also face regulatory requirements that compel them to conduct penetration testing with some level of regularity. 

A sample of regulatory pen testing requirements include:

• PCI DSS (Payment Card Industry Data Security Standard) v4.0.1, which applies to all companies handling credit card data, requires pen testing annually and after significant changes. It also requires retesting after addressing vulnerabilities. 

• SOC 2, which most service organizations that manage customer data must comply with, doesn’t explicitly require pen testing, but most auditors recommend it due to the need for proof of ongoing security evaluations.
• HIPAA, which applies to an organization that manages health data, recently published proposed changes, including an annual pen test requirement.
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Although organizations may be tempted to adopt security best practices from regulations like PCI DSS, keep in mind that many regulations, such as PCI and HIPAA, have been in existence for decades and are slow to make significant changes to their requirements. The pace of change in technology, cybersecurity, and cyberattacking, on the other hand, is not slow. It’s best to remember that, in many cases, regulatory requirements reflect the time they were established, which might not align with the current threat landscape, or cybersecurity innovation. A cybersecurity program that exists only to check the compliance box will not prove effective.

In addition, the time and effort required to conduct a sole annual pen test are significant. Whereas, if you are conducting regular penetration tests, you will have the data you need at your fingertips, easing the data collection and reporting tasks involved in compliance.

Industry guidance on penetration testing frequency

Cybersecurity industry associations, like OWASP, the SANS Institute, ISACA, and CSA, all offer similar guidance on penetration testing frequency. Like the regulators, they recommend a risk-based approach with an emphasis on testing after major changes. In other words, most suggest testing at least annually, but more often for high-risk organizations (like healthcare) or those with fast-moving, dynamic environments.

Benefits of penetration testing more frequently (or continually)

Pen testing is one of the most effective and trusted security testing methods. It doesn’t just unearth hypothetical security issues, but real, exploitable security vulnerabilities. However, it has traditionally been hampered by extreme cost and time constraints, which are especially incompatible with today’s fast-paced, AI-led technology environments.

AI-driven pen testing allows organizations to fight fire with fire and leverage AI to get the effectiveness of a penetration test in a world where AI writes software and generates cyberattacks.

The benefits of conducting frequent or continual AI-driven pen testing include:

• The ability to keep up with fast-moving developers and cyberattackers: A manual pen test will be obsolete before it’s completed in most cases today.

• Less time and expense responding to audits or regulatory requirements: Audit documents are ready in moments, rather than the traditional weeks or months required for a team of people to manually collect and report on data for an audit.
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Make cumbersome pen testing a thing of the past with XBOW

A yearly penetration test is both ineffective and cumbersome. Save time and money, ease the compliance process, and boost your security posture with continual pen testing with XBOW. 

Sign up with XBOW today, and get human-level pen testing results, at machine speed. In one week, you’ll have compliance-ready documentation with validated findings.

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