“How often should we run a penetration test?” is one of the most common questions we get — and the honest answer is: there is no universal frequency. Testing once a year and feeling safe confuses a snapshot with a programme. The better approach is a tailored pentest programme anchored to your actual risk.
What Defines a Good Pentest Programme
A well-considered programme answers four questions:
- Which tests are needed? External infrastructure, internal infrastructure, web applications, IoT, cloud?
- What scope — and where does regular vulnerability scanning sensibly complement the manual test?
- What frequency per test type?
- Which triggers justify an unscheduled test?
The Factors That Set the Frequency
How often you should test depends on several variables: company size, criticality of the data, industry threat level, compliance requirements (PCI DSS, ISO 27001, DORA, NIS2) and, not least, budget. An online retailer handling payment data has a different profile from a local trade business.
The Solid Minimum Line
There is one constant: an external infrastructure penetration test once a year should be part of every programme. Larger organisations (from around 100 employees) should also run internal tests, where lateral movement and insider risk weigh more heavily.
When an Unscheduled Test Is Due
Regardless of the calendar, three situations justify a test immediately:
- Major network or architecture changes
- After a security incident — to rule out recurrence
- When deploying new, exposed systems
Following only the annual rhythm means testing exactly not the changes that raised your risk.
How Cloud Cape Helps
We don’t sell an off-the-shelf one-off test — we build a pentest programme with you that matches your risk, your compliance and your pace of change, with a clear minimum line and defined triggers for ad-hoc tests. Where continuous validation makes more sense than periodic testing, we combine it with our Continuous Threat Exposure Management.
Talk to us about Pentesting & Red Teaming — we’ll define the right frequency for your risk, not for a checklist.