How often should you schedule a penetration test? Once a year? Every quarter? Only after a system upgrade? With cybersecurity threats evolving daily and regulatory requirements varying by industry, finding the right testing frequency can feel like a guessing game. But getting it wrong could mean compliance violations—or worse, a data breach. So, how do you strike the right balance? Let’s break down what the regulations say and what your business truly needs.
Understanding Penetration Testing
Penetration Testing, or “pen testing” is a critical risk management tactic in which a security professional mimics a cyber attack on your computer system or chosen networks to identify vulnerabilities.
Why Is Pen Testing Important?
Organizations use penetration testing to:
- Safeguard the security and integrity of information systems, networks, and applications.
- Evaluate vulnerabilities and weaknesses through controlled testing to identify potential security risks.
- Prove compliance with data security regulations like PCI DSS, ISO 27001, and SOC 2, HIPAA.
By incorporating penetration testing into a proactive security strategy, companies demonstrate a commitment to data protection and regulatory compliance.
Regulatory Requirements for Pen Testing
Penetration testing requirements vary depending on industry regulations. However, most frameworks provide guidelines on how and when these tests should be conducted.
Frameworks That Require or Recommend Pen Testing
PCI DDS (Payment Card Industry Data Security Standard):
- Annual testing required and after significant system changes (Requirement 11.3)
- Requires penetration testing for organizations processing or storing cardholder data.
- Identifies potential security threats that could expose financial data.
- While not explicitly required, pen testing helps organizations meet ISO 27001’s vulnerability management requirements
- Highly advised to conduct regular testing as part of an ongoing risk management process
SOC 2 (Service & Organization Controls 2)
- Conducting penetration testing periodically is highly recommended to demonstrate a company’s ability to protect customer data and privacy, as failing to do so is widely regarded as unprofessional and negligent within the industry.
- Helps validate security controls and prevent data breaches.
HIPPA (Health Insurance Portability and Accountability Act)
- Pen tests can be used to prove HIPPA regulation number two, “Identify and protect against reasonably anticipated threats to the security or integrity of the information”
- To protect patients’ privacy and data, pen testing is highly recommended in order to comply with HIPAA regulations
- Risk analysis required but no fixed testing schedule required—appropriate frequency determined by organization
GDPR (General Data Protection Regulation)
- Mandates implementing technical and organizational measures to protect personal data
- Regular testing to ensure the effectiveness of security measures
- Frequency dependent on data sensitivity and processing risks
Types of Penetration Tests for Compliance
External Penetration Testing
- Simulates cyberattacks on an organization’s external networks and systems.
- Testers mimic real-world hackers attempting to access websites, emails, and sensitive data through methods like SQL injection or DDoS attacks.
Internal Penetration Testing
- Evaluates risks from insider threats (e.g., employees, ex-employees, disgruntled employees).
- Simulates how an insider with some system access could escalate privileges and compromise sensitive data.
Hybrid Penetration Testing
- Combines external and internal testing for a comprehensive cybersecurity assessment.
- Uses manual and automated approaches to analyze security weaknesses holistically.
How Much is a Pen Test?
Depending on what you’re looking to get from a pen test, the costs will vary. The costs depend largely on the computer systems, networks, applications, duration of engagement, and the resources required. The general range for pen tests is $5,000–$20,000.
How Often Should You Conduct Penetration Testing?
Conduct pen tests annually to:
- Address emerging cybersecurity threats.
- Ensure consistent IT security management
- Maintain compliance with industry regulations.
Over-testing can lead to unnecessary costs and redundant findings. Organizations should tailor testing frequency based on risk exposure, industry requirements, and security needs.
Common Testing Schedules
- Baseline Frequency: Once or twice a year to meet compliance needs and regulatory standards
- Triggered Testing: After major system changes, security incidents, compliance updates or milestones
- Supplemental Testing: Quarter or semi-annual tests for high-risk environments. Focused tests on specific systems or applications between full assessments.
- Time-Boxed Testing: Conducting pen tests in tandem with each release cycle to test new features
Conclusion
Penetration testing is a key cybersecurity practice that helps organizations identify vulnerabilities before malicious actors exploit them. Furthermore, while annual testing is a best practice, companies should adjust testing frequency based on their risk level and regulatory obligations.
By aligning with compliance standards, conducting regular pen tests, and focusing on high-priority security threats, companies can fortify their security posture while optimizing costs.
Stay ahead of cyber threats—implement a proactive penetration testing strategy today.
