Searching for Web Pentesting Roadmap? If so then here is the best roadmap which you can follow to become a web penetration tester.

Are you concerned about the security of your website? In today’s digital world where everything is accessible online, it’s essential to ensure that your site is protected from potential cyber threats.

That’s why web pentesting or website penetration testing has become an indispensable practice for businesses and organizations worldwide. By identifying vulnerabilities in a website, you can mitigate risks before they turn into costly disasters.

In this blog post, we’ll take you through a step-by-step guide on how to conduct successful website pentesting by following a comprehensive roadmap. So buckle up and get ready to learn the art of finding vulnerabilities!


Methodology is the backbone of any successful web pentesting roadmap. It provides a structured approach to identify and exploit vulnerabilities in a website systematically. Following a well-defined methodology helps ensure that all possible attack vectors are explored, and no defects are left uncovered.

The most common methodology used for web penetration testing is the Open Source Security Testing Methodology Manual (OSSTMM). This methodical approach consists of seven phases including information gathering, threat modeling, vulnerability analysis, exploitation, post-exploitation, reporting and reassessment.

In addition to using an established methodology such as OSSTMM or Penetration Testing Execution Standard (PTES), it’s also essential to have a customized plan based on specific business requirements. A bespoke strategy can help uncover unique vulnerabilities that may not be detected by standard approaches.

Moreover, during the web pentesting process, ethical hackers need to document every step they take carefully. Accurate documentation ensures transparency throughout the entire process and offers insights into what was tested and how it was tested.

Following a comprehensive methodology while conducting website penetration testing ensures thorough coverage of all attack surfaces within an application or platform while minimizing risks associated with missed vulnerabilities or incomplete assessments.

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Footprinting is one of the most crucial steps in web pentesting, as it involves gathering information about the target system. This phase provides a foundation for further analysis and helps build an attack strategy.

During footprinting, we collect data such as IP addresses, domain names, email addresses, contact numbers and employee details to map out our target’s digital presence. We can use several tools like Whois Lookup or Google Search Operators to obtain this information.

Once we have all the necessary information about our target website or application from open sources, we move on to more advanced techniques like social engineering or network scanning for additional data.

It is important to note that footprints should be left behind in a controlled manner and not affect the availability of services on the targeted website/application. As ethical hackers, it is our responsibility to ensure that there are no negative consequences while performing penetration testing.

Footprinting plays an essential role in understanding how attackers might approach your systems by providing valuable insight into security vulnerabilities. It also underlines why organizations must prioritize cybersecurity measures to protect sensitive data from cyber threats.


Reconnaissance is a crucial phase in web penetration testing that involves gathering information about the target system and its environment. This step helps to identify potential vulnerabilities, weaknesses, and entry points for exploitation.

During reconnaissance, it’s essential to collect as much data as possible from both public and private sources. Open-source intelligence (OSINT) techniques such as social engineering, dumpster diving, and searching online forums can be used to gather valuable information about the target system.

Moreover, passive reconnaissance methods like WHOIS lookup or DNS enumeration can reveal critical details such as IP addresses or domain names of the target server. Network mapping tools like Nmap can also be used during this phase to discover open ports on the network.

Additionally, active reconnaissance involves probing the target system using various scanning tools like vulnerability scanners or port scanners to determine potential vulnerabilities that could be exploited by attackers.

Reconnaissance is a vital step in web pentesting since it provides a comprehensive understanding of the target environment before launching an attack on it.


Scanning is the third step in a web pentesting roadmap, and it involves probing the target website to identify possible vulnerabilities that could be exploited. The goal of scanning is to gather as much information about the website’s infrastructure as possible, including its network topology and any open ports or services.

One of the most popular tools for scanning is Nmap, which can help you discover hosts and services on a network. You can also use vulnerability scanners like Nessus or OpenVAS to automatically check for known vulnerabilities in web applications.

During scanning, it’s important to pay attention to any anomalies or unexpected results that might indicate a potential weakness. For example, if you find an open service on an unusual port number, this could suggest that there’s something out of place.

However, it’s worth noting that scanning can sometimes generate false positives or trigger security alerts from intrusion detection systems (IDS). It’s therefore important to have permission from the owner of the target website before conducting any scans.


Exploitation is the phase where a pentester uses his technical skills to take advantage of the vulnerabilities found in the previous phases. This is where all the hard work and preparation finally pays off. The objective of exploitation is to gain access to sensitive data, elevate privileges, or even take over an entire system.

The first step in exploitation is identifying which vulnerability can be exploited and how it can be leveraged to achieve the set goal. A pentester may use various techniques such as SQL injection, cross-site scripting (XSS), buffer overflow attacks, or social engineering tactics depending on what was discovered during reconnaissance and scanning.

Once a vulnerability has been identified, a proof-of-concept must be created to verify that this vulnerability exists and can indeed be exploited. A successful proof-of-concept demonstrates that an attacker could exploit this vulnerability if they wanted to.

After testing out different exploits for each identified vulnerability, a pentester will attempt to execute them against the target system. It’s important at this stage not only to have technical expertise but also knowledge of legal boundaries because executing these exploits without permission might lead you into trouble with law enforcement agencies.

When all vulnerabilities have been exploited successfully by using different techniques tested before; documented evidence should be collected about every compromise made so that they can provide valuable feedback about potential security improvements needed on clients’ systems while ensuring confidentiality throughout reporting procedures via secure communication channels between parties involved in penetration testing process.

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After the web pentesting process is completed, reporting is an essential step. The report should be detailed and include all of the vulnerabilities that were found during the testing. This report will help developers to understand how their website can be exploited by hackers and what measures they need to take in order to fix these issues.

The web pentester needs to clearly communicate any potential risks associated with each vulnerability. They also need to provide recommendations on how these vulnerabilities can be fixed efficiently. It’s important for this information to be presented in a clear manner so that developers can easily understand it.

Moreover, the report must contain actionable steps that developers can take right away. The goal is not only finding vulnerabilities but also providing solutions and guidance on how they can address them quickly. It’s important for pentesters not just point out problems, but collaborate with development teams offering possible solutions.

In addition, it’s crucial for the report to prioritize findings according to severity level – High/Medium/Low- so that developers know which issues require immediate attention and which ones are less critical.

Creating an easy-to-understand yet comprehensive report is a vital part of the web pentesting process as it helps organizations improve their website security posture while making sure attackers cannot exploit any weaknesses within their system(s).

Read More : How to Write Bug Bounty Report


Resources are crucial when it comes to web pentesting. Having access to the right tools and knowledge can make a significant difference in finding vulnerabilities effectively.

One of the essential resources for web pentesters is books. There are numerous books available on various aspects of web application security, such as OWASP Top 10, SQL injection, Cross-Site Scripting (XSS), etc. These books provide an in-depth understanding of concepts and practical examples that can help you identify vulnerabilities.

Online courses and tutorials are also valuable resources for learning about web penetration testing. Platforms like Udemy, Pluralsight, Coursera offer several online courses specifically designed for beginners who want to learn about web app security or hone their skills further.

Another resource widely used by professionals is bug bounty programs offered by companies ranging from small startups to large corporations. Bug bounty programs allow you to test real-world applications while getting paid bounties for discovering vulnerabilities.

Online communities like Reddit’s r/NetSec subreddit or HackerOne community forums can be excellent resources for getting answers to technical questions or participating in discussions with other experts in the field of cybersecurity

Having access to diverse resources is essential when it comes to building your knowledge and expertise as a web pentester.

Conclusion: Web Pentesting Roadmap

Web pentesting is a crucial aspect of securing any website or online platform. The process requires technical knowledge and expertise in various fields, including networking, programming, and security systems.

By following the roadmap outlined above, you can develop a reliable methodology for finding vulnerabilities on any website. Remember to use all available resources and stay up-to-date with the latest techniques to ensure that your approach remains effective over time.

Web pentesting is an ongoing process that requires constant attention to detail and a willingness to adapt as new threats emerge. By committing yourself to this important work, you can help keep the internet safe for everyone who uses it.


Web penetration testing, also known as web pen testing, is the process of testing a web application or website for security vulnerabilities.

Some common web application vulnerabilities include SQL injection, cross-site scripting (XSS), cross-site request forgery (CSRF), file inclusion vulnerabilities, and authentication bypass vulnerabilities.

There are many tools used in web penetration testing, including Burp Suite, OWASP ZAP, Nmap, Metasploit, and Nessus, among others.

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