Web Penetration Testing, also known as a web pen-test, simulates a cyber attack on your online digital assets to identify exploitable vulnerabilities. Pen-testing is often used to complement a Web Application Firewall (WAF) in the context of web application security.

Web Penetration Testing may include attempting to penetrate any number of application systems (e.g. Application Protocol Interfaces or APIs, front-end/back-end servers) to discover vulnerabilities such as unsanitized entries vulnerable to Remote Code Execution (RCE), SQL Injection, and other types of attacks.

The penetration test results may be used to fine-tune your WAF security rules and address the vulnerabilities found.

Web Penetration Testing Stages

The web pen-testing methodology is divided into five main steps.

1. Planning and Reconnaissance

This first step entails:

  • Defining a test’s scope, including the systems to be evaluated and the testing framework to be used.
  • Obtaining OSSINT or Open Source Intelligence (e.g., network and domain names, mail server, whois) to understand better how a target operates and potential weaknesses.

2. Vulnerability Scanning

This stage determines how the target application will react to various intrusion attempts. This is usually done via:

  1. Static Scanning – inspecting an application’s code to estimate how it will behave while operating. These tools are capable of scanning the entire code in a single pass.
  2. Active Scanning – The technique of analyzing an application’s code while it is running is also known as dynamic analysis. This scanning method is more practical since it gives a real-time picture of an application’s performance.

3. Exploitation

This stage employs web application assaults such as cross-site scripting, SQL injection, and backdoors to identify weaknesses in a target. To understand the potential impact of these flaws, testers attempt to exploit them by increasing privileges, stealing data, intercepting conversations, and so on.

4. Persistence

The purpose of this step is to determine whether the vulnerability can be abused to maintain a presence in the compromised system long enough for a bad actor to get in-depth access. The goal is to mimic sophisticated, persistent attacks, which may stay in a system for months and steal an organization’s most sensitive data.

5. Evaluation and Reporting

The penetration test findings are then collected into a report that includes:

  • Executive summary and risk score
  • All vulnerabilities found within the engagement
  • Specific flaws that were successfully exploited
  • Evidence of access to sensitive information
  • The length of time the pen-tester was undetected by the system
  • Recommendations for mitigation and remediation

Security experts use this data to assist tune an enterprise’s WAF settings and other application security solutions in order to fix holes and guard against future assaults.

Most Common Web Penetration Testing Methods

External Test

External penetration test targets a firm’s internet-visible assets, such as the web application itself, the corporate website, emails and Domain Name Servers (DNS). The objective is to obtain access to and extract useful information.

Internal Test

In an internal test, a tester having access to an application behind the company’s firewall mimics a hostile insider attack. This is not always emulating a renegade employee. A frequent starting point is an employee whose credentials were obtained due to a phishing attempt.

Blind Test

In a blind test, a tester is merely provided with the name of the targeted organization. This gives security workers a real-time view of how an actual application assault might occur.

Double-Blind Test

Security professionals in a double-blind test have no prior information about the simulated attack. As a result, they won’t have time to shore up their reinforcement before an attempted breach, much as in the real world.

White Box Testing

In this scenario, the tester and the security staff collaborate and keep each other informed of their movements. This excellent training exercise offers a security team real-time feedback from a hacker’s perspective.

Finally, pen-testing meets some of the requirements for security auditing procedures, such as PCI DSS and SOC 2. Specific requirements, such as PCI-DSS, may only be met using a certified WAF. However, because of the benefits mentioned above and the flexibility to upgrade WAF settings, doing so does not make pen testing any less helpful.


Rhyno delivers a range of activities that combine to fully protect your infrastructure and data from cybercriminals, anywhere and everywhere, 24/7/365.


About Rhyno Cybersecurity Services

Rhyno Cybersecurity is a Canadian-based company focusing on 24/7 Managed Detection and Response, Penetration Testing, Enterprise Cloud, and Cybersecurity Solutions for small and midsize businesses.

Our products and services are robust, innovative, and cost-effective. Underpinned by our 24x7x365 Security Operations Centre (SOC), our experts ensure you have access to cybersecurity expertise when you need it the most.

immediate help

This website uses cookies to improve your online experience. By continuing, we will assume that you are agreeing to our use of cookies. For more information, visit our Cookie Policy.

Privacy Preference Center