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How Often Should a Company Do
Penetration Testing?
Most companies ask the wrong question.
They ask: “Do we need penetration testing?”
The better question is: “How often should we test?”
Software changes all the time.
Code ships. Features launch. Systems change.
Risk changes with every update.
This guide explains how often companies should run penetration testing in a simple and practical way.
In this guide you'll learn:
Why annual pentesting is only the starting point
What determines how often you should test
When companies should test more frequently
How modern teams handle security testing today
Built for security leaders and engineering teams who need practical testing decisions.
Designed around how modern systems actually change - not outdated annual assumptions.
How Often Should Companies Do Penetration Testing?
In the past, companies tested once a year.
But today systems change much faster.
Applications update often. Cloud systems change. New integrations appear.
When systems change, risk also changes.
This guide helps security leaders understand when testing should happen and why frequency matters.
Core Insights from the Guide
Security Changes Fast
Most systems change often, but testing happens slowly.
Testing Should Follow Change
The more your system changes, the more often you should test.
Better Visibility
Frequent testing helps find issues earlier and fix them faster.
Trusted by Innovative Teams
See what security and engineering leaders have to say about our continuous testing approach.
Shai Bhula
Chief Technology Officer, Whip Around
“The platform made it easy to scope, schedule, and track the test in real time—no long email chains or delays.”
Sarah Webb
Chief Operating Officer, LawVu
“Capture The Bug's continuous pentesting approach has been a game-changer for us at LawVu.”
Jacques Labuschagne
CTO, PaySauce
“We would highly recommend Capture The Bug to anyone who needs continuous assurance and speed without compromising depth.”
Security Testing Should Match How You Build
Penetration testing is important.
But testing once a year may not be enough for modern systems.
Download the guide to learn how often companies should test and how to avoid security surprises.