Evolution of Automated Penetration Testing: Toolchains, Integration Strategies, and Operational Challenges

An essential component of cybersecurity is penetration testing, which finds flaws in systems or networks before attackers take advantage of them. It involves modelling cyberattacks to evaluate the effectiveness of security measures. It targets individuals, offices, buildings, and computer systems to ensure proper setup and prevent illegal access. Penetration testing is a common practice in organisations to strengthen cybersecurity defences. McDermott's [15] paper "Attack Net Penetration Testing" discusses methods to detect, approach, and eliminate system errors using the "error scheduling method.". This thesis focuses on the sixth step in the MiTM attack process, enhancing and applying errors. McDermott's attack network structure is used, with intermediate and final goals identified as nodes on a map and commands. Input is a token used to determine the current position on the map. Under ideal circumstances, finding an easier route to the target or using this route in a secondary attack can open the route for further use. Mirjalili et al. [16] proposed designing and developing a distributed framework for automated web graphics testing. Its main components are an executor executing an attack and a control unit called an orchestrator that organizes it in a series of layers. Besides providing an integrated method, they defined a flexible method for integrating external tools to achieve desired hacking goals by mapping vulnerabilities of framework-integrated tools to realize the full potential of this distributed framework, such as scalability, distributed nature, and ease of use, enabling users to create and deploy applications that leverage the resources available quickly. This framework provides a comprehensive solution for building a distributed hacking system, allowing users to access, edit, and add tools to the system with minimal user-friendly effort, making their attacks more efficient and respond quickly to changing circumstances to exploit vulnerabilities before they are patched. As a result, the system enables users to be nimble and agile when exploiting vulnerabilities, allowing them to stay ahead of their opponents. This gives users unprecedented power and flexibility in their hacking activities.

Consumers looking to improve their cybersecurity can get help through a multi-pronged hacking system. Although distributed hacking has its advantages, there is a problem, which is the process synchronization. Nonetheless, it is hampered or limited by its need for global expertise and resources, as well as global security awareness, fault tolerance, and error recovery. Fredz et al. [1] described ten major attacks related to web apps based on the famous web vulnerabilities of the Open Web Application Security Project (OWASP) project. Recommended edge web threats and associated countermeasures were discussed and covered in this paper. The authors of this paper provided a summary of the OWASP Top 10 Web Application Security Risks as well as full explanations and graphical details that show how each risk has evolved through time. The report talked about web security and how different types of threats affect various businesses, and how different security initiatives affect different businesses. They talked about the best ways to handle security risks and policies. The Study will help businesses understand web application security and implement the right countermeasures. With this summary of the OWASP Top 10, this report hopes to aid businesses in proactively preventing issues with their web applications. In a bid to strengthen their web applications, firms adopted risk reduction methods, acknowledged OWASP’s Top 10 security concerns and understood the current threat landscape. The study also revealed the need to educate web application developers about the Top 10 vulnerabilities identified by OWASP and the use of safe coding practices. They also discussed how to stop them and how to test web application vulnerabilities via automated security scans. Neha [17]’s thesis, Automated Penetration Testing, examines the necessity of having an automated penetration testing in order to reduce the time and cost involved in manual penetration analysis. Doing penetration testing early and often during network or software development stages is easier and cheaper. It takes time to identify or resolve issues instead of waiting until the end of the process. The paper developed a web-based system that launched various vulnerable exploitation (DoS) attacks. The application was able to handle basic DoS attacks using three protocols: Hypertext Transfer Protocol (HTTP), Session Initiation Protocol (SIP), and Message Control Protocol/Internet Protocol (TCP/IP). There were up to two to twenty attacks for each protocol. The rich man, a friendly interface, accepts the input of an IP address for an attack and the port number that identifies that attack. The application completed this attack with one user-friendly interface, making penetration testing easier than manual attacks. The weakness of this approach is that it will be scaled up in the future, and there is a need to continue using external systems to gather information before attacking. It wasn't his first architecture that was established; application development is limited and possibly inefficient. The lack of integration of a port or IP discovery program is reduced. The intelligent and dynamic nature of the system. This thesis aims to build a framework that can be established before developing a web application to ensure long-term viability and integrate systems for full system functionality. Roy et al. [18] offer a taxonomy-based survey in their comprehensive analysis of adversarial reconnaissance strategies. Reconnoitering tactics such as target footprinting, social engineering, network scanning, and local discovery are categorized by the taxonomy according to their technological approach. Doupé et al. [2] evaluated ten web application evaluation tools: Acunetix, AppScan, BurpSuite, Arachni, Hailstorm, NTOSpider, Paros, N-Stalker, Webinspect, and W3af. These resources were chosen with consideration for both commercial and open-source scanners. Hu et al. [19] provided a thorough analysis of the state-of-the-art security vulnerability detection technology and the process of developing machine learning technology. A cross-site scripting security vulnerability detection model for web applications is designed and implemented, and the requirements of the security vulnerability detection model are fully analyzed. By adding the verification code identification function, the issue of data submission to the server requiring the verification code only to be entered is resolved. This function is based on the current network vulnerability detection technology and tools. Li [20] coordinated industry norms. Development teams can review and address code vulnerabilities to reduce false positives found in static scans and penetration tests, aiming for increased accuracy of the findings. This application security framework combines the top 10 OWASP vulnerabilities and 25 dangerous CWE/SANS software errors in a matrix with Checkmarx vulnerability queries. Using Checkmarx vulnerabilities queries to map OWASP/SANS, defects, and vulnerabilities are shown to be managed more effectively. Noman et al. [21] provided a literature assessment summarizing security solutions and significant flaws to stimulate more study by constructing a system of the current approaches on a larger horizon. They stated that more research on digital information security is needed because there is no way to mitigate all online vulnerabilities fully. Additionally, they spoke about how complicated the procedures in the survey were and offered some advice on how to use them. Luo et al. [22] OWASP identifies the most important network vulnerabilities according to the Top 10, including their associated attacks and countermeasures. They also proposed an application that provides protection against the most severe attacks by web applications and prevents some zero-day exploits. Amankwah et al. [10] used two insecure online apps, WebGoat, and Damn insecure online Application, to compare the vulnerability detection skills of eight web vulnerability scanners (both open and commercial). OWASP ZAP, IBM AppScan, Acunetix, HP WebInspect, Vega, Iron WASP, Skipfish, and Arachni were the eight WVSs examined. Multiple assessment metrics were used to assess the performance, including the web application security scanner evaluation criteria, Youden index, precision, recall, and OWASP web benchmark evaluation. The experiment's findings demonstrate that, although commercial scanners are effective in identifying security flaws, some open-source scanners (like ZAP and Skipfish) can also succeed.

2.1 Summary of literature review

This section provides a details summary of the literature review. As shown in Table 1, the focus of the summary is to find gaps in the literature and possible solutions to overcome the gaps. A total of eleven papers from the literature are reviewed, and a summary is provided.

Table 1. Gap analysis between the research papers

Though still with room for development in several areas, the evolution of automated penetration testing (APT) has solved many conventional security issues. McDermott's work on attack network penetration testing emphasizes the need for a thorough method to include automated tools and frameworks for scalable and efficient testing. In order to fill this gap, output and efficiency will be significantly increased by employing machine learning techniques to identify and prioritize weaknesses. Similarly, the automated web graphics testing system developed by Mirjalili et al. [16] is deficient in synchronization and fault tolerance features. These capabilities would include enhancing the framework's scalability and reliability through the use of robust synchronization techniques and advanced error recovery strategies. The web application security risk studies by Fredz et al. [1] point out flaws but don't provide any helpful guidance on secure coding practices or developer education. Developers could receive OWASP training. Their development processes can incorporate automated scanning tools and the top ten vulnerabilities to offer a solution. Although Neha Samantha's APT thesis provides a web-based solution, it ignores scalability and integration with external systems. By maximizing resource utilization, utilizing parallel processing techniques, and permitting seamless integration with reconnaissance systems, these limitations can be addressed. The classification of adversarial reconnaissance techniques by Roy et al. [18] and other studies emphasizes the necessity of real-world case studies and practical application guidelines. The gap between theoretical models and their implementation will be reduced with practical training and the development of practical guidelines for these techniques. Similarly, Doupé et al. [2]'s assessment of web vulnerability tools offers useful analysis but no efficacy comparison. Businesses would be better guided in their tool selection if these tools were scored based on specific vulnerabilities. Hu et al. [19]'s work on security vulnerability detection technology provides a model, despite the lack of practical testing. The effectiveness of the same can be checked and made better by working with the industry players for extensive testing and collection of feedback. Jinfeng Li's method may accurately identify flaws, but it is not consistent with contemporary development procedures. To make sure it gets adopted by development cycles, we will integrate it with CI/CD systems and create IDE plugins. Noman et al. [21] literature review missed the emerging issues and talked about current web security practices. To keep up with the changing threat landscape, research projects and collaborations with academic and commercial organizations are necessary. Just like before, Luo et al. [22] thinks the web application security project doesn’t require updates or monitoring. To defend against evolving threats, real-time threat detection systems are implemented that are regularly updated. Amankwah et al. [10] compared web vulnerability scanners, and while they had no user-centered assessment standards, it is useful. If integration's customization and usability are incorporated into the study, the organization will choose tools to meet operational requirements. By promoting a proactive and vigorous digital defense ecosystem, these advances in automated penetration testing research have the potential to significantly advance cybersecurity endeavors.

Despite the considerable advancements made in the field of automated penetration testing (APT), a critical gap remains unaddressed in the literature—the lack of an integrated, scalable, and user-friendly solution that consolidates the strengths of multiple APT tools into a unified platform. Most existing frameworks and tools either operate in isolation or provide limited support for orchestrating multi-tool workflows. Studies such as those by Mirjalili et al. [16] and Neha [17] have proposed distributed or web-based architectures, but they often fall short in areas like process synchronization, centralized reporting, scalability, and real-time configurability. Similarly, comparative analyses of vulnerability scanners tend to emphasize detection accuracy or coverage but rarely assess usability, interoperability, or support for continuous integration pipelines.

This study positions itself as a distinct contribution by addressing these shortcomings through the development of a Python-based graphical user interface (GUI) platform that brings together widely-used APT tools—including OWASP ZAP, Burp Suite, FOCA, and Vega—within a single, cohesive environment. The platform supports multi-threaded vulnerability scanning, real-time result visualization, customizable scanning parameters, and a robust reporting module that classifies vulnerabilities by severity and recommends mitigation strategies. Importantly, the system is designed with accessibility and extensibility in mind, allowing both novice and experienced cybersecurity professionals to perform comprehensive assessments without needing to manually operate or switch between tools. Furthermore, the proposed framework introduces a curated taxonomy of over 75 security vulnerabilities, offering a systematic evaluation of how integrated tools perform across diverse attack vectors, including advanced threats such as GraphQL injection, insecure CORS configurations, and cross-site WebSocket hijacking.

By unifying toolchains and abstracting complex security operations through a modular, GUI-driven platform, this research bridges the gap between academic exploration and practical application. It not only enhances efficiency and scalability in penetration testing workflows but also democratizes access to advanced security assessments—marking a significant advancement in the field of automated cybersecurity solutions.

Research concerning vulnerabilities in cybersecurity has unmasked a plethora of complex threats that place the safety of contemporary systems and structures at risk. Manipulation of input fields and code insertion by hackers is made easier using two of the most common flaws, SQL Injection (SQLi) and Cross-Site Scripting (XSS). Unauthorized access to databases through error-based or time-based injections is known as SQLi, while execution of scripts inside the victim browser is known as XSS. These myriad forms of fundamental errors highlight slack adaptational policies concerning input validation and sanitization on systems of a network. Attacks such as Cross-Site Request Forgery (CSRF) and Server-Side Request Forgery (SSRF) are some of the most common. The illegal actions using a user’s authenticated session are what the fair use policy, CSRF, contravenes. In contrast, SSRF takes advantage of flaws made by a server’s configuration to breach internal networks or perform other unpermitted operations. Addressing such issues requires stringent policies on tokenization and origin-checking. As has been discussed before, underlying problems like these require attention. Insecure Direct Object References (IDOR) and Broken Access Control demonstrate how hackers can get around permissions to access restricted resources. Similarly, vulnerabilities such as Remote Code Execution (RCE) and XML External Entity (XXE) expose the risks associated with improper management of external data inputs and system-level access controls. More complex attacks include Content Security Policy (CSP) Bypass, which gets around regulated areas of access, and permissions are set. The same goes for vulnerabilities like Remote Code Execution (RCE) and XML External Entity (XXE) that showcase the danger of bad handling of external data interfacing. Other, more advanced attacks are Content Security Policy (CSP) Bypass, which circumvents security settings selected by the browser, and GraphQL Injection, which enables hackers to manipulate API calls. Creative with regard to contemporary technological resources, construction methods, and aggression, with dependency confusion and crypto-jacking, demonstrates how contemporary attackers with modern computers have become. Once new vulnerabilities such as Cross-Site WebSocket Hijacking, CSS Injection, and HTML Injection have been identified, the ongoing attack surface in web application development operations grows. The lack of Cryptographic Storage policies and Weak TLS Configurations points towards weak data encryption techniques, which may compromise critical information. This research points out the lack of validation, misconfiguration, outdated security policies, or a single security policy approach as the root cause of many of the listed vulnerabilities. CRLF Injection, for example, is a form of HTTP response modification hacking, where special characters are added to specific fields in a form. Changing the value of a field meant to be protected by security measures is also referred to as parameter masking. Directory Browsing allows navigational access to server files and structures otherwise barred, while Path Traversal takes directory navigation a notch further by enabling unrestricted access. Many of these vulnerabilities have already been mapped out with the use of automated penetration testing tools. They are particularly good at spotting configurable injections, obsolete configurations, and unsecured storage frameworks. Logic-based complications that rely on intuition, like some scripting attacks and subtle privilege elevation, are found to be the gaps in these automated systems. To address these flaws, we must use security best practices, do active manual validation, and regularly run automated tests to ensure reliability. Lesser risks and better resilience of systems can be achieved by means of advanced technology, continual supervision, and intelligence. In order to create proactive and flexible cybersecurity tools of the future, there needs to be research into other advanced tools to keep up with complex and evolving threats.

In our experiments, the integrated GUI-based platform was tested on a simulated enterprise web environment consisting of typical modules such as login forms, search bars, and document upload features. Using Burp Suite Professional and OWASP ZAP through the GUI, the platform successfully detected over 80% of injected SQLi and XSS payloads during initial scans. For example, in one test case, the system identified a time-based blind SQLi vulnerability within the search field of a document repository module, which manual inspection had overlooked. Similarly, a stored XSS vulnerability embedded in the feedback form was accurately flagged with a risk severity of "High" and linked to insecure JavaScript sanitization. These findings support the strength of toolchain integration in capturing common web vulnerabilities in real-time.

However, certain logic-based vulnerabilities like IDOR and privilege escalation were inconsistently detected. For instance, the platform did not raise an alert when a low-privileged user accessed another user's invoice via manipulated URLs — a typical IDOR case. Manual validation complemented automated detection by uncovering such flaws, reinforcing the need for hybrid testing strategies. Figure 1, previously described in the methodology, showcases how the integration of tools, multi-threaded scanning, and live dashboard reporting support a comprehensive vulnerability mapping process. By comparing vulnerability detection performance across different tools, we found that Burp Suite had a higher success rate for CSRF detection, while Vega outperformed in identifying outdated libraries. These comparative insights highlight the importance of tool specialization and provide a rationale for their inclusion in a unified GUI-driven environment.

Table 4 presents a comparative analysis of the vulnerability detection capabilities of the integrated tools. Burp Suite Professional demonstrated high efficacy in detecting SQL Injection (95%), XSS (90%), and CSRF vulnerabilities (92%), whereas OWASP ZAP performed moderately well for XSS and Directory Traversal. Vega proved particularly effective in identifying deprecated libraries, while FOCA excelled in extracting sensitive metadata. However, critical vulnerabilities such as Insecure Direct Object Reference (IDOR) and Server-Side Request Forgery (SSRF) were consistently missed by all tools, necessitating manual validation. This underscores the importance of hybrid testing strategies that combine automated scanning with expert-driven analysis to achieve complete security coverage.

Table 4. A comparative overview of detection effectiveness, highlighting the strengths and gaps across each tool for various vulnerability types