Cyber threats never stand still. Every day, new vulnerabilities and exploits emerge, placing organisations of all sizes at greater risk. Relying on one-time or infrequent security audits is no longer enough to protect valuable data, brand reputation, and customer trust. This is where regular automated penetration testing comes into play.
In this post, we’ll explore what automated pen testing is, why it matters, the pain points it helps solve, how it supports regulatory compliance, and some compelling industry insights that underscore the urgent need for continuous security checks—all in a way that’s approachable, whether you’re a cybersecurity expert or just getting started.
A penetration test is a controlled simulation of a cyberattack, carried out to find weaknesses in your systems before real attackers do. Traditionally, penetration tests were conducted entirely by specialised security teams, which often meant scheduling them once or twice a year. With automated penetration testing, advanced scanning tools replicate much of what a manual tester would do, but on a more frequent or continuous basis.
Think of it as having a constant “cyber guardian” in place, actively probing your websites, networks, and applications for vulnerabilities. Whenever it spots something suspicious—like an outdated software component or a misconfiguration—it flags it so you can fix it quickly. This ongoing approach not only saves time and resources but also ensures that newly discovered weaknesses don’t remain hidden until the next scheduled manual test.
Before examining the benefits of automated testing, it helps to consider the common challenges organisations face when relying on less frequent or fully manual security reviews:
Infrequent tests or scans provide only a snapshot in time. Between tests, new code releases, system patches, and infrastructure changes might introduce fresh vulnerabilities, leaving you in the dark until the next big check.
Manual security assessments can be resource-intensive and time-consuming. Depending on the complexity of your environment, discovering and remediating vulnerabilities can take weeks, and by the time the process completes, new threats may have surfaced.
Skilled manual testers are essential for certain in-depth scenarios, but they can be expensive when used for every routine security check. This financial burden often leads organisations to reduce the frequency of their tests, potentially leaving security gaps.
When businesses finally receive a single, large security report—sometimes running to hundreds of pages—it can be overwhelming. Teams may struggle to decide which vulnerabilities to address first, leading to confusion and slower response times.
Many regulations (GDPR, ISO 27001, PCI DSS, etc.) either recommend or require regular security testing. Relying only on one-off audits can expose you to compliance risks and potential penalties if you fail to maintain continuous protection.
With a “test-once” approach, you’re always playing catch-up—fixing vulnerabilities months after they first appeared. This reactive stance often leads to firefighting rather than proactive prevention.
Automated penetration testing addresses these pain points by providing near-real-time insights, cost-effective scanning, and a steady flow of vulnerability information—making it far easier to stay on top of risks and fix them swiftly.
If you’re wondering whether continuous scanning is really that important, consider a few industry trends and data points that reflect the growing cybersecurity challenge:
The financial impact of cybercrime has grown significantly over the years, potentially reaching colossal figures worldwide. Many businesses underestimate both how frequently and how severely they can be targeted until it happens.
Modern organisations operate across a range of digital platforms—web apps, cloud services, internal APIs, mobile apps, and more. Each system can be a potential entry point for attackers. Having a single annual test for everything often misses emerging threats or newly added systems.
Governments and industry bodies are tightening requirements around data protection. Failure to comply can result in hefty fines, legal complications, and serious damage to a business’s reputation.
A large percentage of data breaches involve exploiting flaws that already had patches available but were never applied. This indicates that many organisations still struggle to maintain up-to-date defences—a problem that a regular testing and remediation cycle can help resolve.
Taken together, these insights show why a more proactive, ongoing approach is essential. Rather than waiting for an annual or quarterly test, continuous testing closes the windows of opportunity for attackers.
With continuous scanning, weaknesses are identified as soon as they appear, rather than lingering in your environment undiscovered. Whether it’s a newly disclosed software flaw or a misconfiguration introduced during an update, an automated pen test can catch it quickly.
Many automated tools can scan a wide variety of systems—websites, APIs, databases, cloud platforms, and more. This helps businesses gain a thorough map of their entire digital estate, reducing the chance that some neglected corner of their infrastructure remains unchecked.
Because automated testing can run on a set schedule (daily, weekly, monthly) or even continuously, you receive near-instant notifications when something critical shows up. Early alerts enable your team to remediate issues promptly, lowering the risk of a successful attack.
While manual tests often require time and specialised security consultants, automated scans cost far less per run. As your organisation grows—taking on new services, acquisitions, or integrations—your automated testing setup can expand without ballooning costs.
Human error or varied testing approaches can lead to inconsistencies. Automated tools apply the same checks regularly, making it simpler to track improvements or spot patterns in recurring vulnerabilities. Over time, you can measure how your security posture evolves based on reliable, repeatable data.
Receiving continuous feedback from each new scan allows your developers and IT teams to address vulnerabilities immediately. This “little-and-often” approach generally works better than tackling a long backlog all at once—making the entire remediation cycle more manageable.
Beyond the immediate advantages of better security, it’s worth noting that preventing a breach can cost far less than dealing with its aftermath. Once an attack succeeds, businesses may face technical recovery expenses, legal costs, notification obligations, and long-term reputational harm. By contrast, consistent automated testing helps you detect and fix security gaps at an early stage, reducing the risk of significant disruptions. In purely financial terms, an investment in proactive measures could be the difference between a quick patch today and a full-scale crisis budget tomorrow.
Alongside the clear security advantages, regular automated penetration testing provides a strong base for meeting various compliance obligations. Here’s a quick look at how ongoing security checks help you stay aligned with major standards:
The General Data Protection Regulation emphasises the importance of safeguarding personal data. Although it doesn’t mandate a specific security tool, it does expect organisations to adopt measures that reflect consistent data protection. Regular automated scans demonstrate that you’re proactively testing for vulnerabilities, reinforcing accountability and due diligence.
This internationally recognised standard for information security encourages organisations to maintain a continuous risk management cycle. Scheduling automated pen tests across your environment is a proactive way to verify you’re regularly assessing the effectiveness of your security controls—an integral part of ISO 27001.
Many industries have unique standards—HIPAA for healthcare, PCI DSS for payment card data, and so on. Most emphasise the need for regular testing. Automated testing not only ensures you meet those benchmarks but also generates documented proof of recurring scan activities, which proves invaluable during audits.
Regular testing means you won’t have to scramble at the last minute to satisfy an auditor’s request. Instead, you’ll demonstrate a steady approach to securing customer data and other sensitive information.
Cybersecurity threats are not slowing down—if anything, they’re getting more sophisticated. Regular automated penetration testing is a practical way to keep pace with these changes. It flags vulnerabilities early, lowers costs compared to solely manual testing, supports alignment with industry regulations, and allows you to spend more time managing your business rather than constantly firefighting security issues.
Why wait to discover a critical security hole only after it’s been exploited? By integrating automated security tests into your regular business processes, you can address threats head-on and show customers and stakeholders that protecting their data is a top priority.
We understand that rolling out frequent security tests across all your systems might feel daunting—especially if you’re accustomed to manual testing or you’re a smaller team with limited resources. Our services provide a streamlined, user-friendly way to embed automated penetration testing into your daily operations, helping you:
Interested in regular automated pen testing? Have compliance queries? We’re here to support you every step of the way. Staying ahead of cybercriminals is far easier—and more cost-effective—than dealing with the fallout of a breach. Let’s work together to ensure your business remains fully prepared. Feel free to contact us at any time to learn more about our services or to discuss a bespoke testing plan.
Remarkable are one of the world’s leading digital experience agencies. As a double Platinum Sitecore and Optimizely partner, we offer technology solutions to help brands build experiences that convert.
