One of the most common questions security leaders ask is:
How often should we run a penetration test?
The short answer: more often than most organisations do.
The right frequency depends on risk, infrastructure changes, and compliance but relying on one-off testing leaves long gaps of exposure.
The Minimum Recommended Frequency
At a baseline, most organisations should run a penetration test:
- At least once per year
- After major infrastructure changes
- After deploying new applications
- After cloud migrations
- Following a security incident
This ensures that new attack paths introduced by change are identified before attackers find them.
Compliance vs Real-World Security
Many organisations test only to meet compliance requirements.
Common standards often mandate:
- Annual or biannual penetration testing
- Testing after significant system changes
While this satisfies auditors, compliance-driven testing does not equal security. Attackers don’t wait for audit cycles.
Why Annual Pen Testing Isn’t Enough
Modern environments change constantly:
- Cloud configurations shift
- New integrations are added
- Permissions drift over time
- New vulnerabilities emerge daily
An annual test captures a moment in time attackers exploit everything that happens after.
When You Should Test More Frequently
You should consider more frequent penetration testing if you:
- Operate cloud-first or hybrid environments
- Release software regularly
- Handle sensitive or regulated data
- Have complex identity and access models
- Want reduced breach risk, not just compliance
In these cases, recurring or continuous testing provides far stronger assurance.
One-Off Tests vs Continuous Testing
| One-Off Pen Test | Continuous Testing |
| Annual snapshot | Ongoing validation |
| Compliance-focused | Risk-focused |
| Long exposure gaps | Reduced attack windows |
| Static results | Adaptive to change |
Security is no longer static testing shouldn’t be either.
How Hacker Simulations Approaches Penetration Testing
Hacker Simulations focuses on real-world attack simulation, designed to mirror how modern attackers operate.
We help organisations:
- Validate security continuously
- Identify real attack paths
- Reduce noise and alert fatigue
- Focus remediation on what actually matters
We don’t train teams.
We test reality.
Final Takeaway
If your environment changes regularly, annual penetration testing is not enough.
The right question isn’t “Are we compliant?”
It’s “How long are we exposed?”
