How often should you run a penetration test?

There is no single right frequency. Annual testing is the common baseline because certifications, insurers and customer contracts tend to ask for it, but the right answer depends on how fast your environment changes and what it protects.

Why it matters

A test is a point-in-time snapshot. Every deployment, migration and new integration after it erodes what the report can tell you. Matching test cadence to your rate of change keeps the assurance real instead of ceremonial.

A sensible cadence

• Annually as a baseline, which is what most frameworks, insurers and tenders expect
• After significant change: a new internet-facing application, a cloud migration, a major upgrade
• Before go-live for systems that will hold sensitive data or face the internet
• After an incident, to confirm the door that was used is actually closed
• More often for high-change environments, where rotating focused tests beats one annual monolith

Stretching the value between tests

Continuous vulnerability scanning between tests catches newly disclosed flaws in the systems you already had tested. Retesting remediated findings closes the loop on the last report. Together they mean the annual test starts from a known position rather than rediscovering the same issues.