Introduction
You’ve been told that you need to get an annual penetration test or pentest—but you’re not entirely sure what to do. In this article, we’ll explore what an annual pentest is, why it’s important, how to pick a pentest service provider, and more.
In today’s rapidly evolving digital landscape, cybersecurity is no longer a luxury but a necessity. With cyberattacks growing in frequency and sophistication, businesses are finding it critical to safeguard their systems, networks and sensitive data.
So, regardless of what industry you’re in or what kind of penetration test you’re looking for, this article can help.
What is an Annual Penetration Test?
A penetration test (pentest) is an authorised, controlled, and simulated attack on your digital systems by trained penetration testers (ethical hackers or pentesters).
A penetration test aims to identify and exploit vulnerabilities that a real-life cyber-criminal could exploit. Then, report those vulnerabilities back to you with some remediation advice so your organisation can begin patching those vulnerabilities.
To learn more about penetration tests, check out our comprehensive guide.
An annual penetration test is the practice of conducting a pentest at least once a year to ensure your system remains secure over time and compliant with industry and vendor regulations.
New vulnerabilities can appear as new software updates, business applications, and technologies are integrated into your digital systems. Additionally, new, previously unknown vulnerabilities can come to light over the year. So, an annual pentest enables you to stay on top of your cybersecurity and maintain a healthy and robust security posture.
Why are Annual Penetration Tests Important?
We’ve already discussed some of the main reasons for conducting annual penetration tests, but let’s explore them in more detail.
Evolving Cyber Threats
Cyber threats constantly change, and what was considered secure a year ago may now be vulnerable. New hacking techniques, malware, and zero-day exploits emerge every day. By conducting an annual pentest, you ensure your organisation is aware of and protected against these emerging threats.
Compliance Requirements
One of the most common reasons organisations order annual pentests is compliance, and if you’re reading this because you’ve been told you need an annual pentest, this would be our first guess as to why. Many regulatory frameworks, such as PCI-DSS, HIPAA and GDPR, require organisations to test the security of their systems regularly. An annual pentests helps meet these legal obligations, demonstrating that your business is committed to safeguarding sensitive data.
Business Continuity and Reputation
A single breach can have devastating effects, including financial loss, legal consequences, and reputation damage. In the worst-case scenario, businesses can collapse entirely. Annual pentesting minimises the chances of a cyberattack disrupting your operations. It also shows your customers, investors, and other stakeholders that you take cybersecurity seriously, which is becoming increasingly important.
Detecting New Vulnerabilities
New applications, updates, and system changes often introduce unknown vulnerabilities. An annual pentest ensures you identify and patch these vulnerabilities before they can be exploited, helping you stay ahead of potential attackers.
Common Misconceptions Regarding Annual Penetration Testing
Pentests are Only for Large Enterprises
This is one of the most common and dangerous misconceptions. Cyberattacks can happen to organisations of all sizes, and small-to-medium enterprises (SMEs) are increasingly targeted due to their often weaker security defences. So, the truth is, annual pentests are critical for any organisation, regardless of size.
Pentests Are Too Expensive
While pentesting requires an investment, the cost of a successful cyberattack can be far higher. The financial, reputational and mental fallout from a successful breach can be devastating. Annual pentesting helps prevent such costly incidents.
For companies who don’t have the resources to test everything, instead of testing the same thing every year, like your external network infrastructure, test something new every year. This way, over a few years, you will have tested everything. While this does leave things vulnerable in the years they’re not being tested, it’s better than not testing.
Once-a-Year Pentesting is Enough
Although annual pentesting is a crucial component of a cybersecurity strategy, it should not be your only line of defence. Continuous monitoring using automated scanners, regular vulnerability assessments, and proactive security practices must complement yearly pentests to provide complete protection.
When Should I Book My Annual Penetration Test?
The timing of your annual pentest can be critical. Many companies book their annual pentest at the end of the year in a panic when they realise they haven’t done one. This panic and short timeframe can be dangerous—vulnerabilities can be missed, and errors can be made, which leave your organisation vulnerable to cyberattacks—especially if you don’t work with a certified pentest service provider.
Ideally, you should schedule it after significant changes to your systems, such as:
New Software or System Deployments
If you’ve introduced new business applications or cloud services, a pentest can identify vulnerabilities specific to these changes.
Major Security Updates
After a significant patch or update to your internal and/or external network infrastructure, it’s essential to test if the new changes inadvertently introduce vulnerabilities.
Compliance Deadlines
Many regulatory frameworks have specific deadlines for security assessments. To remain compliant, ensure your annual pentest aligns with these deadlines.
It’s also wise to avoid booking a pentest during periods of peak business activity, as the testing process can occasionally cause minor disruptions to systems and networks.
How to Choose an Annual Penetration Test Service Provider?
Selecting the right pentesting provider is a critical decision. Here’s what to look for:
Experience and Certification
Ensure that the provider has qualified, experienced professionals. A safe bet is to look for service providers with internationally recognised certifications such as OSCP (Offensive Security Certified Professional), CEH (Certified Ethical Hacker), CHECK (managed by the National Cyber Security Centre or NCSC) or CREST (Council of Registered Ethical Security Testers) certification.
Proven Methodology
A reputable provider will follow established pentesting methodologies, such as the OWASP (Open Web Application Security Project) or NIST standards. This ensures a thorough and structured approach to testing your systems. That said, highly reputable pentesters will also have methodologies that may be more relevant to your needs.
If you want to learn more about OWASP, check out our OWASP Top Ten blog.
Manual Testing vs. Automated Scanning
While automated tools help scan for known vulnerabilities to find more complex, hidden vulnerabilities, you require a manual test from a skilled ethical hacker.
Some companies offer penetration testing but, in reality, only use automated scanners. These automated scans will not give you enough depth, will produce a high volume of false positives, and lack contextual understanding.
Check out our comparison article to learn more about automated scanning and manual penetration testing.
Detailed Reporting
After the test, the provider should deliver a comprehensive report detailing vulnerabilities, their severity, and remediation recommendations. Look for providers who offer clear, actionable insights, not just technical jargon.
Is technical jargon is causing you a headache? Check out our Cyber Security Glossary.
Industry-Specific Experience
If your business operates in a highly regulated industry, such as healthcare or finance, choose a provider with experience in your field. They will better understand the unique threats and compliance requirements you face.
Conclusion
So, now you know annual penetration testing is essential to any robust cybersecurity strategy, all that’s left is to book it.
By ensuring that your systems are up to date, emerging vulnerabilities are identified, and regulatory requirements are met, you can protect your business from potentially devastating cyberattacks.
By understanding the importance of annual pentests and taking a proactive approach to cybersecurity, you safeguard your operations, protect customer data, and maintain your reputation in an increasingly digital world. Make it a point to schedule regular tests and choose a trusted provider to keep your organisation secure.