Web Application Pentesting Approaches


Approaches to web application pentesting
What is Penetration Testing?

Penetration testing, also known as pen testing, is the practice of testing a computer system, network, or web application for security vulnerabilities. Penetration testers are hired to attempt to exploit vulnerabilities to determine if unauthorized access or other malicious activities are possible. The prime focus of the modern-day penetration testing market is on delivering tangible business value and real-world risk mitigation.


Penetration testers use a variety of methods to attempt to exploit vulnerabilities, including manual testing, automated tools, and reverse engineering. They may also attempt to exploit vulnerabilities in order to gain access to systems or data, or to cause damage to systems or data.

Penetration testing is often used to assess the security of systems and applications, to find and fix vulnerabilities before they can be exploited by attackers, and to verify the effectiveness of security measures.


Nowadays, penetration testing is a professional and well-defined activity, often governed by professional certifications, such as the Certified Ethical Hacker (CEH) credential offered by the EC-Council. Penetration testers are employed by organizations to attempt to exploit vulnerabilities in systems in order to assess the security posture of the organization.


Ethical hacking is the process of attempting to penetrate a computer system or network using the same methods as a hacker, but with the permission of the organization being tested. The purpose of ethical hacking is to find and fix security vulnerabilities so that the system remains secure.



Web Application Penetration Testing Methodology

The application penetration test methodology can be summarized in the following steps:

1. Identify the application

2. Review the application and understand its functionality

3. Identify potential vulnerabilities in the application

4. Exploit the identified vulnerabilities to gain access to sensitive data

5. Report the findings to the executives


The first step in any application penetration test is to identify the application. The second step is to review the application and understand its functionality. This includes understanding how the application works, what features it has, and how it is used. The third step is to identify potential vulnerabilities in the application. This includes identifying vulnerabilities in the application code, design, and functionality. The fourth step is to exploit the identified vulnerabilities to gain access to sensitive data. This includes using the vulnerabilities to gain access to user data, administrator accounts, and other sensitive data. The fifth step is to report the findings to the executive board of the company. This includes reporting the findings to the application owner, developers, and other stakeholders who may have a vested interest in the security of the application.


The results of application penetration testing are as follows:

1. Detailed analysis of vulnerabilities and their root causes.

2. Identification of specific remediation guidelines for vulnerabilities.

3. Improved understanding of the organization's internal processes and SDLC (Software Development Life Cycle).

4. Improved ability to assess the effectiveness of security controls.

5. Improved ability to assess the impact of vulnerabilities on the organization.


The final report is a comprehensive guide that helps organizations understand the security posture of their applications, identify and fix vulnerabilities, and improve their overall security posture.



Web penetration testing scope and approaches

A pentest scope defines the boundary and limits of a penetration test. The scope should be well-defined and agreed upon by both the pentester and the client before starting the test. The pentester should also be familiar with the organization's network, systems, and applications so they can plan their tests accordingly.

The following are some factors that should be considered when defining the pentest scope:

1. The business objectives of the organization

2. The systems and applications that need to be tested

3. The security posture of the organization

4. The pentester's expertise and experience

5. The time and budget constraints


Based on the factors above, the pentester can then identify the systems and applications that need to be tested, the type of tests that need to be performed, and the level of security risk that the organization is facing.


Open-source security testing methodology manual (OSTTM) is a popular, well-recognized open source framework for penetration testing. It is a comprehensive guide that covers the entire testing process, from planning to post-test reporting. OSTTM is written in a step-by-step style and provides a lot of detail, making it a good choice for experienced testers. However, it can be a bit overwhelming for newcomers.


PCI DSS (Payment Card Industry Data Security Standard) is a well-known framework for securing credit and debit card information. It is a comprehensive set of requirements for organizations that process, store, or transmit credit card data. While it is not specifically designed for penetration testing, it can be used as a framework for performing security assessments.


OWASP (Open Web Application Security Project) is a global, nonprofit organization that creates freely available resources on application security. One of OWASP's most popular resources is the OWASP Top 10, a classification of the most common application security risks. OWASP also provides a number of other resources, such as a guide to performing penetration tests. OWASP is a good choice for testers who are new to application security.


The OWASP Top 10 is the result of a global consensus process involving over 120 experts from around the world. The OWASP Top 10 is organized into the following categories:

1. Injection flaws

2. Cross-site scripting

3. Broken authentication and session management

4. Insufficient logging and monitoring

5. Insecure communications

6. Broken access controls

7. Security misconfiguration


This includes mapping out all digital and IT assets, understanding how they are interconnected, and assessing the potential security risks associated with each. Only after a full holistic assessment can AI Web Security application penetration testers identify the most effective and relevant attack vectors to test.