This guide helps you determine how often security testing should occur based on risk, sensitivity, and exposure. It explains how to combine periodic testing with event-driven retesting so that testing cadence reflects how risk actually changes over time.
How organizations typically get this wrong
Treating annual testing as sufficient regardless of exposure, sensitivity, or system churn. Assuming that “nothing changed” internally means risk is unchanged. Retesting entire environments when only a small subset has materially changed. Increasing testing frequency without improving remediation, validation, or scoping discipline. Using calendar cadence as a substitute for risk analysis.
How penetration testing fits
Penetration testing evaluates specific systems or applications within a defined scope. It is best used when the goal is to validate technical controls or identify exploitable weaknesses.
How attack simulations and red teaming differ
These approaches test how the organization responds to realistic attack paths that span people, process, and technology. The emphasis is on exposure and response, not individual findings.
Choosing the right approach
The right choice depends on readiness, clarity of ownership, and how results will be used. In many cases, starting smaller produces more useful outcomes.