Web applications are like children—they grow every day, need constant care, and often get into trouble. They change daily, if not hourly, with new features, third-party integrations, and API updates, and each modification introduces new potential security vulnerabilities.
Critical security findings within web applications rose a staggering 150% in 2024. Yet, many organizations rely on yearly penetration tests to uncover these issues. This infrequent testing leaves massive gaps in coverage, exposing businesses to potential data breaches and financial losses.
Continuous penetration testing ensures that security keeps pace with development, allowing organizations to detect and remediate web application vulnerabilities in real-time.
Continuous penetration testing is a security assessment methodology that, like other web app pen testing types, involves simulating real-world attack scenarios to uncover vulnerabilities. However, unlike traditional penetration testing, which happens at point-in-time intervals, continuous testing is an ongoing scan that provides real-time insights into evolving attack surfaces and emerging vulnerabilities.
Web applications are intricate and ever-changing by nature, making them moving targets for attackers. This makes them difficult to secure with static, point-in-time testing.
Aside from being susceptible to common risks, such as OWASP's Top 10 risks, they are also exposed to complex threats like zero-day to API vulnerabilities. Continuous pen testing requires a blend of automated scans and expert-led manual testing to spot and adapt to these threats.
Security is not a one-time event, and neither should your security tests be. As web applications grow more complex and threats evolve rapidly, relying on traditional, point-in-time penetration testing is no longer enough. Comparing traditional and continuous penetration testing helps highlight the advantages of investing in a more modern tool and approach.
Traditional penetration tests, typically done once a year or quarterly, often miss vulnerabilities introduced between testing cycles. Continuous penetration testing, however, provides near-real-time visibility into new risks, identifying vulnerabilities as soon as they are introduced (such as through code changes or new features), making it a proactive and ongoing process.
Business logic involves deeply understanding an application’s unique use cases, target customers, potential ‘worst-case scenarios,’ and specific risks. It enables more tailored and context-driven testing, prioritizing identified vulnerabilities based on their relevance and potential impact on the business.
Solutions like Terra Security make this approach truly effective. Terra leverages AI agents to perform continuous testing, create tailored attacks, and deliver context-based findings specific to your company's business risks.
A core objective of continuous testing is ongoing compliance, which is particularly crucial for organizations in highly regulated industries. Achieving compliance is one hurdle, but the challenge lies in maintaining it as web applications evolve and change over time. Continuous penetration testing ensures compliance requirements are consistently met with every code deployment, minimizing the risk of penalties for non-compliance.
Continuous penetration testing helps identify vulnerabilities early, allowing security teams and developers to prioritize and fix issues quickly. Reducing the time between detection and resolution minimizes disruptions to user journeys and limits exposure to potential attacks.
Web applications are complex ecosystems spanning APIs, authentication mechanisms, third-party integrations, and more. Continuous penetration testing aims to identify vulnerabilities across the entire attack surface.
Most continuous web app pen testing tools, like network-focused tools, rely on hardcoded attack scenarios. However, web apps are unique. Their critical vulnerabilities hide in deep, complex, multi-step attack chains that hardcoded methods can’t replicate. To find these vulnerabilities, teams need more than AI tools: they need real-time reasoning from experienced human testers.
Traditional tools lack human reasoning and real-time adaptability, leading to shallow scans, false positives, and missed critical findings. Without understanding the business context, they fail to prioritize real risks or offer meaningful remediation, leaving security teams with more noise than insight.
Terra changes that by training AI agents to think and adapt like humans. It delivers deeper, more accurate testing while involving humans in critical decisions.
Now, let’s look at how to implement and execute continuous penetration testing. There are multiple tactics involved, including:
Continuous penetration testing typically relies on automated tools for ongoing scanning and monitoring, with occasional manual testing for more complex or nuanced vulnerabilities. Testers identify potential exploits and use tactics and custom payloads to attack the weakness.
If a vulnerability is exploitable, it is automatically prioritized based on its potential business impact, with actionable remediation recommendations provided. On the other hand, non-exploitable vulnerabilities are deprioritized, as the core objective of pen testing is to identify threats that can cause actual harm to the business rather than those lacking proof of exploitability or significant impact.
It’s essential to log and record every change continuously. Attack surface mapping involves identifying all assets within an attack surface, whether inside or outside the organization’s direct control. Then, you need to categorize these assets and check them for vulnerabilities. Business logic helps here, as you can easily understand the connection between various assets and gauge the criticality of a vulnerability.
Adversary emulation simulates attacks by replicating the tactics of specific cybercriminal groups, mimicking their behavior and methods. On the other hand, breach simulation uses tools to simulate specific attack events, testing how well security measures respond to targeted threats. Both leverage ethical hacking strategies to identify vulnerabilities, but adversary emulation focuses on attack strategies, while breach simulation tests specific incidents.
Each web application has its architecture, dependencies, and security protocols, as well as use cases, data, and risk profiles. Exploitation testing is even more powerful when tailored to a specific web application. This approach aims to get as close as possible to real-world attack scenarios. It’s one thing to say an attack is potentially possible, but another thing to point to a vulnerable API endpoint that can be used to modify API requests and gain unauthorized access.
This continuous exploitation doesn’t stop at finding a single exploit but continues with attacks to find even more. Pivoting means moving laterally within the system after the initial breach. This technique is effective because this is precisely how an attacker behaves in the real world. The initial breach is only the start- an attacker would typically look to move laterally within the system and gain additional privileges.
Any business that runs a web application benefits from continuous pen testing, but here are a few examples of industries where it is imperative in:
E-commerce companies are prime targets for cyberattacks, as they handle vast amounts of sensitive customer data and rely on complex digital ecosystems, from payment gateways to e-commerce price monitoring tools. Cybercriminals constantly probe these systems for weaknesses, aiming to exploit vulnerabilities in checkout flows, APIs, and third-party integrations. Continuous penetration testing helps e-commerce businesses reduce the risk of payment fraud, ensure PCI DSS compliance, and protect consumer trust.
Modern manufacturing facilities use IoT devices and lab automation software to enhance productivity, and these integrations introduce new security challenges. They also have many web applications and thus have a vast web attack surface. By adopting continuous penetration testing to secure their factory infrastructure, manufacturers can uncover sensors and other equipment vulnerabilities, preventing potential attacks that can cause production downtime and customer data leaks.
Banks, digital wallets, and fintech startups face increasing cyber threats, ranging from API exploitation to account takeover fraud and sophisticated phishing schemes. Continuous pen testing is crucial for these institutions to identify threats early and prevent fraudulent transactions. It also helps improve customer confidence in online banking services.
Continuous penetration testing is crucial for organizations operating in high-risk, customer-facing industries. As new vulnerabilities rapidly emerge and web app environments become more dynamic, continuous penetration testing ensures real-time vulnerability detection, rapid remediation, and compliance adherence.
Terra takes continuous penetration testing to the next level with the first-ever agentic AI platform for offensive security. By combining the scalability and coverage that only AI agents can provide with the expertise and precision of human testers, Terra empowers organizations to secure their web apps proactively.
It scans your web applications continuously, delivering context-aware insights relevant to your business. With almost complete attack surface coverage, continuous compliance checks, and tailor-made attacks, it helps you uncover every vulnerability and risk within your web applications. Request a demo to learn more.
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