Published October 27, 2026
For a lot of teams, the pen test shows up the same way every year. An audit is coming, the auditor wants a report, and someone books a test. That's a reasonable start, and it's often exactly what the framework asks for.
But your applications don't change once a year, and neither do the ways attackers get in. The better question isn't whether to test. It's how often, and how much to test each time.
What your auditor actually asks for
Most frameworks set a minimum, and some don't set one at all:
Sources: PCI Security Standards Council, ISO, HHS, AICPA Trust Services Criteria. The HIPAA update is still a proposed rule as of October 2026.
ISO 27001 and SOC 2 leave the cadence to you. That flexibility is useful, but it means your auditor will ask how you decided. "It's what we did last year" is a harder answer to defend than a plan built on risk.
Your risk doesn't run on an audit calendar
In Verizon's 2026 Data Breach Investigations Report, exploiting vulnerabilities became the most common way breaches began, at 31%, passing stolen credentials and phishing for the first time. Only 26% of known exploited vulnerabilities were fully fixed, and the median time to patch one climbed to 43 days.
No team can fix everything at once, so knowing which issues attackers are actually using matters as much as finding them.
Your applications don't stand still either. Every release, new integration, and AI-assisted feature can change what's exposed. A clean report from last year isn't the same as a clean application today.
Test on a rhythm, not a deadline
Here's our view: for an application that changes, an annual pen test on its own isn't enough. A testing program should run in three layers.
- Scan regularly. Scan internet-facing systems at least monthly, and after every significant change. Scans cover a lot of ground fast and catch known issues early.
- Pen test every significant change. When you ship a new feature, API, login flow, or integration, test it, along with the login, access, and data services it relies on. For teams that release often, that means targeted pen testing monthly or quarterly.
- Run at least one full pen test a year. A full test covers the whole application, including the parts nobody is changing, and gives you and your auditor a complete picture.
This approach follows OWASP's Web Security Testing Guide, which places penetration testing at deployment and then calls for periodic health checks and verification of every change. OWASP also notes that automated tools give you breadth, but the most serious flaws tend to live in business logic and custom code. Strong programs use both.
Regular testing doesn't mean testing everything every time. NIST's security controls let organizations set both how often they test and which parts of a system are in scope. Keep a record of what was tested and when, so you and your auditor can see how the layers add up.
Easier on your team, not harder
Testing more often sounds like more work for your developers. In practice, it usually makes remediation easier.
- Smaller batches. Instead of one large report each year, your team gets a few findings at a time, small enough to fit into normal sprint work.
- Fresher context. Developers fix issues in code they wrote recently, not code they have to relearn months later.
- Simpler fixes. Problems caught early haven't been built on yet, so changing them doesn't ripple through other features.
- Fewer repeat issues. Early findings show the team what to watch for, so the same mistakes show up less often in later releases.
- Evidence as you go. Findings are fixed and retested along the way, so evidence is already in place when your auditor asks.
The bottom line
That's the kind of program Trava is built to run. Managed Vulnerability Management covers the first layer with monthly scans and practitioner triage, so your team sees which findings matter and how to fix them. Managed Penetration Testing covers the other two, with practitioner-led testing on a recurring schedule, so targeted tests keep pace with your releases and your full annual test is already on the calendar. One team runs all three layers, so each one builds on the last instead of living in a separate report.
Ready to build your testing plan? Book a scoping call, and we'll define scope, timeline, and investment together.
