Penetration Testing: How Often Should You Test?

How often should I do penetration testing? It’s a question that comes up regularly. The short answer is: it depends. 

The frequency of pentesting depends on the organization’s specific needs and risk profile, but in general, we recommend performing at least one comprehensive pentest annually. Additionally, we recommend performing regular, targeted pentests, also known as “attack simulations” or “red teaming” to check the effectiveness of their security controls, and to keep your security team sharp.  

Organizations should conduct pentesting whenever there are significant changes to the systems and networks, such as after a major software update or when new assets are added to the network. 

Some industries such as finance and healthcare are required to do regular pentests to prove compliance. But more importantly, it’s not just a matter of proving compliance once per year, you should have ongoing protection. 

Doing a pentest once per year is the equivalent of running antivirus on your computer once per year, and then turning it off. You wouldn’t do it. Your code should be tested constantly. When the developer is writing and submitting code, checks should be running in the background. Every time they deploy something new into their testing environment, checks should be executed. 

We partner with organizations to help them implement automated tools that keep them protected every day. However, the automations do not replace pentesting. Automation will only take you so far, perhaps catching only 50-60% of the issues. You still need manual pentesting. 

Enter our Eureka DevSecOps Service (not to be confused with our Eureka DevSecOps Platform). In our DevSecOps service, we include an annual pentest, which covers all the manual activities. Then, to ensure you have coverage between the annual pentests, we help you install automation so that you’re at least catching the low-hanging fruit.  

Manual Pentesting and Automated Testing

Manual penetration testing involves a human tester using a combination of manual techniques and specialized tools to identify and exploit vulnerabilities in a system or network. This method is considered more thorough and can identify vulnerabilities that automated tools may miss. However, it is more time-consuming and costly compared to automated testing.

Automated Testing, on the other hand, uses specialized software tools such as:

  • SAST (Static Analysis Security Testing)
  • SCA (Software Composition Analysis)
  • DAST (Dynamic application security testing)
  • IAST (Interactive application security testing solutions)
  • RASP (Runtime Application Security Protection)

To learn more about each of these tools, check out our post: How You Can Automate Application Security

Essentially, these automated tools can quickly scan a large number of systems and networks to find vulnerabilities. While this automated testing is faster and less costly than manual testing, it may not be as thorough.

Furthermore, automated tools are often used late in the SDLC, causing development teams to face increased pressure to resolve hard-to-detect vulnerabilities and may result in even more security risks.

Both manual and automated testing have their own advantages and disadvantages and a combination of both methodologies should be used for a more comprehensive security assessment. Automated tests can be used to quickly identify common vulnerabilities, while manual tests can be used to confirm the results and identify more complex or unknown vulnerabilities.

We recommend doing at least one manual pentest per year, perhaps twice depending on your budget. As mentioned, manual testing is labour-intense, and with labour costs being high, these manual tests can be expensive. So, you shouldn’t be doing it every day.

Security Training

In addition to pentesting to keep your code safe, an often overlooked area where companies can increase their security posture is through training their employees. 

Training your staff to be security conscious is a good thing because it can help to mitigate a wide range of security risks. Some of the benefits of training your staff include: 

  • Increased awareness: By training your staff on security best practices and the latest threats, they will be more aware of the risks and more likely to identify and report suspicious activity. They will also be more likely to follow security procedures and take responsibility for protecting the organization’s data and assets. 
  • Better incident response: By training your staff on incident response procedures, they will be better prepared to respond to security breaches and minimize the damage caused. 
  • Compliance: Many regulations, like HIPAA and PCI-DSS, require regular security awareness training for staff, so this is necessary for compliance. 
  • Human factor: The human factor is the most common cause of security incidents, and by training your staff to be security conscious you can reduce the risk of security incidents caused by human error. 

Training your staff to be security conscious is a good thing because it can help to mitigate a wide range of security risks and improve the overall security posture of the organization. 

At Forward Security offer security training We also train your developers to ensure they are building secure code. This helps prevent a lot of issues from happening in the first place. 

If you decide to work with us on an ongoing basis, we can bring DevSecOps into the picture so that you have continuous coverage in addition to the annual pentesting. 

Connect with one of our security experts today to learn more about our DevSecOps service and Eureka platform.