How Often Should You Run a Pentest?

"Once a year" is the default answer most organizations settle on, often because it is what a compliance framework explicitly requires, not because anyone concluded it was actually the right cadence for their specific environment.

Compliance minimums are a floor, not a target

Frameworks like PCI-DSS specify a minimum testing frequency, typically annual, plus after significant infrastructure changes. Treating that minimum as the actual target, rather than the absolute floor, is a common and understandable but ultimately risky habit.

Concrete triggers that should prompt a test regardless of schedule

• A major new feature or application component ships, particularly one handling sensitive data or new authentication flows.
• Infrastructure moves to a new provider, or a significant new environment goes live.
• A merger or acquisition brings new systems and codebases into scope that were never previously tested under your organization's standards.
• A significant vulnerability class is publicly disclosed that plausibly affects your technology stack.
• A previous engagement's findings were remediated and need verification through a proper retest, not just an internal confirmation that a fix was deployed.

This is the core argument for a continuous model

Organizations with fast-moving development cycles increasingly find that a fixed annual cadence cannot keep pace with how quickly their actual attack surface changes. See why continuous penetration testing wins for what a more responsive alternative to the fixed-schedule model looks like.

A practical starting point

If you are not sure where to start, treat "annually" as a true floor, add a test after any of the triggers listed above regardless of where you are in the annual cycle, and reassess after a year or two whether your actual rate of change justifies moving toward a more continuous model.