A Comprehensive Guide to Penetration Testing

Penetration testing (pen testing) is a proactive way to assess the security of your organisation’s infrastructure, applications, and networks by simulating real-world cyberattacks to uncover vulnerabilities before criminals do. Unlike automated scanning alone, pen testing combines tools with human expertise to identify complex weakness chains that standard assessments can miss.

This 2024/2025 buyer’s guide explains what effective penetration testing looks like, why it matters for risk management, and how it supports compliance requirements (including frameworks such as POPIA, PCI DSS, HIPAA, GDPR, and ISO 27001). It also breaks down the end-to-end pen testing lifecycle—from planning and reconnaissance through scanning, vulnerability assessment, exploitation, and actionable reporting—so teams can understand what to expect and how to prepare.

You’ll also learn how to choose the right testing approach (black box, white box, or grey box), when to use automated versus manual testing, and how to evaluate providers with practical questions around methodology, certifications, data protection, reporting quality, and retesting.