What is Continuous Penetration Testing?

With cybercrime always evolving, there’s a lot of pressure on business owners to ensure their network security posture is up to scratch. After all, hackers are constantly finding new ways to exploit vulnerabilities, leak data, and cause reputational and financial damage.

Continuous penetration testing is the process of regularly analyzing your security posture, often when your infrastructure changes. It’s a type of security testing that doesn’t have a set time frame – rather, it’s a scheduled practice that keeps pace with an ever-changing threat landscape.

In this guide, we’ll look at the benefits of hiring continuous penetration testing services, when you should conduct these checks, and how they can help prevent cyberattacks.

What is Continuous Penetration Testing?

Continuous penetration testing is a regular security practice where you simulate cyberattacks to discover vulnerabilities and misconfigurations in your IT infrastructure.

It’s more proactive than running occasional tests and often involves using artificial intelligence (AI) and real-time monitoring.

Traditional penetration testing takes place inside and outside networks and infrastructure, simulating typical cyberattacks in real time.

This means, for example, checking internal weaknesses and functionality (e.g., through APIs and storage practices) and potential backdoors through public apps.

It’s also frequently split into red team (offensive) and blue team (defensive) strategies – meaning you get a 360-degree view of your posture.

The main benefit of penetration testing, by and large, is that it gives business owners insight into how secure they appear to outside threats.

However, traditional penetration testing can take extensive time, budgeting, and planning – which is why some business owners conduct it occasionally.

Continuous testing, meanwhile, aims to test infrastructure and networks more frequently. The idea is to protect corporate data as threats evolve and technology advances. It’s sometimes known as penetration testing as a service (PTaaS).

Setting up traditional penetration testing can require extensive effort and scheduling. However, businesses can conduct ongoing checks more efficiently by using agile development platforms with the support of security professionals.

For example, while Firm A only tests its security posture once or twice a year, Firm B sets up an ongoing assessment plan backed by automated vulnerability scanning for 24/7 oversight.

Of course, continuous penetration testing methodologies have pros and cons, which we will explore in more detail below.

When Should You Consider Continuous Penetration Testing?

Ideally, it’s worth considering continuous penetration testing if you’re:

• Safeguarding high-value data or assets.
• Regularly altering your infrastructure or introducing new technologies (meaning you have a changing attack surface).
• Making large changes to your operation after every annual penetration test.
• Experiencing regular security incidents.
• Interested in innovations that require operational risks.
• Working in fields where compliance requirements change frequently (e.g., PCI DSS for payment card processing).

That said, any kind of regular penetration testing leads to security enhancement. We recommend businesses undertake penetration tests frequently. However, one company’s security program might look different from another’s.

If your needs aren’t so intensive, an alternative option is point-in-time security monitoring – which is more periodic and less explorative.

Even if your needs don’t fall under any of the above, there are still benefits to running penetration testing more regularly.

Benefits of Continuous Penetration Testing

Running automated vulnerability scanning and hiring penetration testers to assess your network regularly ensures your infrastructure is always prepared for the worst.

However, if you’re on the fence about bringing penetration testing in on-demand, there are a few sweeping benefits worth considering. Let’s explore them.

Continuous Learning and Adaptation

The alarming speed at which technology and cybercrime are evolving means there are always new vulnerabilities to account for and new compliance requirements to adhere to.

Many business owners simply find it difficult to keep up with the evolving landscape, especially if they’re only running annual penetration tests.

Businesses that are frequently retesting and re-analyzing their postures learn to spot false positives and adapt to the evolving challenges they face.

Regular tests can help to educate staff and ensure their incident response and remediation facilities are more reactive to security issues.

Helps To Meet Compliance Requirements

No matter the industry you work in, regulatory requirements will always exist. Continuous penetration testing helps companies keep up with compliance demands while evolving their information security strategy.

Running regular or continuous tests means you have less compliance ground to make up throughout the year.

That means there’s less risk of you falling foul of fines and legal action due to compliance neglect.

Reduces The Risk of Successful Attacks

Ultimately, the more often you run in-depth tests and update your security controls, the less likely it is that hackers will successfully breach your perimeter.

As mentioned, technology can evolve a lot in the space of a year. If you run annual tests and find serious weaknesses in old software versions every 12 months, your risk of getting successfully attacked will increase.

Testing and patching your security posture, with or without the help of security teams, only lasts so long. Therefore, it makes sense to test and remedy flaws more regularly.

Reduced Cost of Remediation

The more often you test and fix security problems, the less expensive they are likely to be. Catching a networking flaw within one or two months compared to catching it within a year could mean less work and less risk.

That means there’s immediately less for you to pay for labor in preventing cyberattacks, and likely less for you to pay should anything go wrong.

Disadvantages of Continuous Penetration Testing

Continuous penetration testing might not be the best option for all businesses. Here are some potential disadvantages to consider.

Costs and Resource Demands

Although continuous penetration testing offers fantastic visibility into your security posture, it also comes at a more frequent, regular cost.

Continuous testing requires specialized labor outside of automated scanning, and if you’re testing more than once or twice a year, your costs will naturally increase.

Running tests more frequently will also increase resource usage, potentially slowing down your infrastructure.

Complexity in Scope and Coverage

Regular penetration testing can require complex planning and scoping, depending on your individual needs. This is especially true if your setup changes frequently due to technological and customer demand.

However, you can mitigate this with a clear plan and by working closely with cybersecurity experts who can reduce complexity by putting together a few best practice suggestions.

Potential Privacy Concerns

Some firms prefer not to have their data and infrastructures analyzed and tested more regularly purely for privacy reasons.

This can be reasonable. However, some intrusion is to be expected if you’re aiming for certification in ISO or NIST frameworks, for example. Provided you work with reliable, legitimate cybersecurity specialists, you should have no cause for concern.

Overwhelming Volume of Data

Regularly testing your mobile application security, firewall, and data protection standards will generate a lot of data. This is particularly the case if you are running automated vulnerability scanning.

Test providers recommend using programs and tools that cleanly manage data – meaning it’s easy to refer to in the future. It’s easy to fall into the trap of creating data lakes with endless reports – but not if you use the right tools and have the best partners.

Best Practices for Implementing Continuous Penetration Testing

Naturally, the way you manage continuous security testing may vary from how another firm manages it. However, we’ve compiled a few different practices to consider if you want to make continuous testing part of your standard operations.

Determine the Frequency

How often do you introduce new features to your products, services, or infrastructure? Do you regularly edit code or change your network around, and how critical is the data that these changes impact?

These questions should help you determine how frequently to run penetration tests. You could run vulnerability scanning in the background to monitor for issues ad hoc and reserve full, manual tests whenever you make sweeping changes.

Set Clear Objectives and Goals

Think carefully about the data you’re handling and the processes you’d like to be tested. Consider the areas of your business that would be most at risk from cyberattacks and where, should a data leak or an attack occur, the most damage could be inflicted.

It’s also worth monitoring the latest security concerns, such as the OWASP Top Ten, a list regularly compiled by the Open Web Application Security Project.

Being clear about what you expect from penetration testing is one thing, but you should also plan to communicate clearly with testers and experts.

Consider asking:

• How can a penetration test help me – what tools and services are available, and how might they support my needs?
• Is continuous penetration testing necessarily recommended for my use case? If not, what do experts recommend?
• How can we keep communication open and fluid when working with each other?
• What does the threat validation process look like? How do we know if we’re at risk or need support?

Blend Manual Testing and Automated Scanning

Automated scanning is ideal for spotting minor or common flaws that are easily fixed ad hoc—and sometimes critical vulnerabilities. However, you shouldn’t rely on it wholesale for managing broader network security.

Instead, consider using a blend of manual and automated tools. Manual penetration testing will often dive deeper into specific problems, and manual testers can apply context to particular issues they spot.

Regular Review of Testing Processes

In time, you might find that continuous penetration testing every quarter is too costly and not valuable for your firm. Your infrastructure and environment will change over time, so you might need to change testing and remediation processes.

The key aspect to keep in mind here is flexibility. Be ready to make changes to your security assessment plans, and don’t run tests or fix issues unless there is a genuine need. Build a threat modeling approach that also considers the opinions and insights of different experts and users.

Conclusion

Your security strategy should always evolve – you can’t expect a single fix to endure years of technological and hacking evolution!

Therefore, running continuous penetration can be highly useful for many companies in spotting new threat actors and vectors and challenging baseline security measures. That said, it might not be cost-effective for all businesses.

Regardless, it’s important to consider how effectively you assess and manage your network and infrastructure security. Contact VikingCloud to work together on a sustainable solution that suits your needs and budget.