How often should a website be penetration tested?

At least once a year and after major releases, infrastructure changes or new integrations that handle user data, with automated scans running in between.

What is the difference between a vulnerability scan and a pentest?

A vulnerability scan is automated and lists known issues. A penetration test adds human expertise to exploit and chain weaknesses the way a real attacker would.

Do small businesses need penetration testing?

Yes. Small sites are frequent targets of automated attacks, and any site collecting personal data has GDPR security obligations.

2026-09-25 · 6 min read · by Greta Rusecke, ISTQB Certified QA Specialist

Why Regular Penetration Testing Keeps Your Product Safe

TL;DR A penetration test simulates a real attack to find vulnerabilities before criminals do. Because code, dependencies and threats change constantly, pentests should be repeated regularly — not run once.

What is penetration testing?

Penetration testing (pentesting) is an authorised, simulated attack on a website, application or network. The goal is to find security weaknesses — such as injection flaws, broken authentication or exposed data — and fix them before a real attacker exploits them.

Unlike automated vulnerability scanning, a pentest combines tools with human thinking to chain small weaknesses into realistic attack paths.

Why one pentest is not enough

Your code changes — every new feature can introduce a new vulnerability.
Dependencies age — libraries you use get new publicly known vulnerabilities (CVEs).
Configuration drifts — permissions, cloud settings and access rules change over time.
Attack techniques evolve — methods that did not exist last year are used today.
Compliance expects it — GDPR requires appropriate, regularly tested security measures.

What a pentest typically checks

OWASP Top 10 risks such as injection, broken access control and misconfiguration.
Authentication, session handling and password reset flows.
Exposure of personal data, API keys and admin areas.
Form abuse, spam and bot attacks.
Server headers, TLS configuration and third-party scripts.

How often should you run a pentest?

A common baseline is at least once a year, plus after any major release, infrastructure change or new integration handling user data. Between pentests, automated security scans and dependency checks should run continuously.

Security is part of QA

Security testing belongs in the same quality process as functional testing. Treating it as a regular, planned activity — not an emergency reaction — protects your users, your data and your reputation, and is far cheaper than recovering from a breach.

Frequently asked questions

How often should a website be penetration tested?: At least once a year and after major releases, infrastructure changes or new integrations that handle user data, with automated scans running in between.
What is the difference between a vulnerability scan and a pentest?: A vulnerability scan is automated and lists known issues. A penetration test adds human expertise to exploit and chain weaknesses the way a real attacker would.
Do small businesses need penetration testing?: Yes. Small sites are frequent targets of automated attacks, and any site collecting personal data has GDPR security obligations.