Penetration testing is a crucial technique that involves simulating a cyberattack on networks, computer systems, or online applications in order to test defenses and find any vulnerabilities that might be used by malevolent actors.

This procedure is an essential part of every company’s cybersecurity plan since it acts as a preventative step to ensure the security and integrity of important data and system infrastructure.

The frequency and timing of conducting external penetration testing is a commonly asked subject, especially by both startups and well-established enterprises. The response varies and depends on a number of variables. These include the quantity and complexity of the organization’s systems, the size of the attack surface that faces the Internet, the sensitivity of the data that has to be protected, the company’s overall risk tolerance, and its compliance requirements.

Given the diverse array of penetration testing types — such as internal, external, web application, mobile application, Software as a Service (SaaS) penetration testing, red teaming, etc., — it can be challenging for organizations to discern the appropriate test type, the right time to conduct it, and the frequency of these tests to ensure a continually strong security posture across all their digital platforms.

Best Practices for Scheduling Penetration Testing Frequency

An annual penetration test is a good starting point for startups and smaller businesses. This regular procedure not only helps to find and fix security vulnerabilities on a regular basis, but it also significantly reduces the risk of a cyberattack. Additionally, it helps ensure that regulatory compliance requirements are followed and makes vendor risk assessments easier to do.

Penetration testing should be done more frequently, ideally once a quarter, for organizations that deal with sensitive data or are more vulnerable to cyber threats. These include healthcare organizations, governmental agencies, research-intensive businesses, financial institutions, and e-commerce platforms. This is especially important for these kinds of organizations because of the strict regulations they have to follow and the increased risk of data breaches.

Larger corporations, especially those with intricate network structures or those in the tech/SaaS sector undergoing perpetual development (like constant system upgrades or new device integrations), stand to gain from more regular penetration tests. The complexity and dynamic nature of these environments makes them harder to safeguard, with new vulnerabilities potentially emerging swiftly. Consequently, a quarterly penetration testing regimen is advisable for these organizations.

Certain firms might opt for continuous or as-needed penetration testing, particularly those with a greater risk appetite or those operating within highly regulated sectors. While this method demands more resources, it offers the most thorough level of security safeguarding.

How frequently should pen testing be conducted according to compliance standards?

Various regulatory compliance obligations dictate the frequency of penetration testing for organizations, each with its unique requirements:

PCI DSS: Penetration testing must be done every year or after every major infrastructure change, especially in the area where cardholder data is stored. For further information, see our in-depth guide on PCI penetration testing or Requirement 11 of the PCI security rules.

HIPAA, SOC 2, ISO 27001, LGBA: While there is no specific mandate for penetration test frequency under these standards, prevailing industry best practices suggest conducting such tests at least once every year.

Indicators That You Need a New Penetration Test

Wondering if the time is right for a fresh penetration test: To assist in making this decision, consider the following set of questions to determine the necessity of a new pen test.

• Has a significant period, such as a year or a quarter, elapsed since your last penetration test within a particular scope?
• Have there been recent updates or major alterations to your infrastructure, particularly in critical systems, networks, or applications?
• Did you conduct a subsequent test to verify the effectiveness of patches applied to vulnerabilities?
• Have you introduced numerous new features to your SaaS platforms in the recent past?
• Are you in the process of preparing for certification in SOC 2, ISO 27001, or any other Information Security Management System (ISMS)?
• Are you considering a penetration test as part of due diligence during mergers and acquisitions, or in anticipation of an Initial Public Offering (IPO)?

Why Retesting Matters in Cybersecurity:

It’s critical to conduct a follow-up pen test whenever a company completes an initial penetration test and implements the suggested fixes and patches described in the report.

It is a calculated move to carry out additional penetration testing to gauge how solid the security improvements implemented following the first evaluation are.

Furthermore, this iterative testing procedure is essential to verifying the system’s ongoing security. Retesting is frequently incorporated into the overall penetration testing services offered by top-tier cybersecurity companies.

Why should organizations conduct regular penetration testing?

Organizations can proactively check for security flaws in their networks, systems, and applications by regularly conducting penetration tests. This process is very different from the more traditional style of penetration testing, which is often done once a year or as an isolated incident. Using a continuous penetration testing process has several important benefits.

• Early detection of security vulnerabilities is facilitated, granting organizations the opportunity to rectify these issues before they become targets for exploitation.
• Continuous penetration testing ensures ongoing awareness of the security status of an organization’s systems, reinforcing the necessity of keeping them updated with the most recent security enhancements.
• Cultivating a security-conscious culture within an organization is a key benefit, as it heightens employee awareness regarding the critical nature of security and the constant need for vigilance.
• Integrating penetration testing into the regular operational procedures of an organization can lead to a reduction in the costs traditionally associated with such security measures.

Incorporating continuous penetration testing into an annual security plan is a crucial component of any organization’s overarching cybersecurity framework.

Preparing for a Penetration Test: Key Steps for Your Organization

Ensuring your organization is well-prepared for a penetration test involves several critical steps.

Initially: it’s imperative to select a reputable penetration testing (pentest) provider. This means thoroughly vetting potential providers by checking their references and reviews. For further insights into choosing the right provider, refer to our detailed blog.

After choosing your provider: the next step is to clearly define the pen test’s scope. Determine which specific components and data will be under scrutiny.

Additionally: it’s important to decide on the amount of time and resources you’re ready to invest in the pen test.

Preparation also includes technical readiness: update and patch all systems, eliminate superfluous accounts and permissions, and restrict access to confidential data.

These preparatory measures ensure your penetration test is executed in a secure and well-regulated environment.

Conclusion

The size and type of the firm determines how often penetration tests are conducted. Larger enterprises may need regular testing, but startups and smaller businesses should strive for at least one annual test. The actual frequency should be in line with the specific goals and needs of the company.

Finding security flaws and determining which network segments require more regular testing require conducting a risk assessment. Make use of the results from earlier evaluations to guide and improve your next testing plan. Organizations must set up a clear plan for penetration testing and set aside the funds and resources required for this crucial security precaution.