Web Server Penetration Testing: Definition, Checklist & Tools

As web servers become an increasingly popular target for cybercriminals, it is more important than ever for businesses to ensure that their systems are secure. One of the best ways to do this is through web server penetration testing, which involves simulating a cyberattack to identify vulnerabilities. 

This blog will introduce web server penetration testing and how to carry it out effectively. We will give a cursory overview of the web server penetration testing checklist, some of the most widespread vulnerabilities in web servers, and what you can anticipate during a pen-testing engagement.

What is Web Server Penetration Testing?

Web server penetration testing, also known as web application security assessment or server pen test, is a process of identifying vulnerabilities in a web server. To carry out an effective test, businesses need to understand their web server architecture and how it works clearly. They should also know what type of data is stored on the server and how it is accessed.

This type of test is used to look for vulnerabilities in the server software, hardware, or set-up that attackers may exploit. Web application security testing may also be used to evaluate the web server's security and any applications and data hosted on it.

Importance of Server Penetration Testing

One of the main reasons why hackers target web servers is that they often contain sensitive information such as customer data, financial records, and intellectual property. If malicious individuals obtain this information, it might be used for identity theft, fraud, or other harmful activities. In certain situations, attackers may also gain access to the server and use it to launch attacks on other systems.

Another reason web servers are attractive targets is that they are often connected to the internet, giving hackers a more comprehensive range of attack methods to choose from. For example, they can exploit vulnerabilities in the web server software or carry out denial-of-service attacks that disable the server.

Vulnerabilities in Web Servers

Several common vulnerabilities are often found in web servers. These include:

  • Unsecured administrative access: This is one of the most common problems found during web server penetration testing. Suppose an attacker is able to gain administrative access to the server. In that case, they can view and modify sensitive information, install malicious software, or carry out other activities that could jeopardize security.

  • SQL injection attacks: An SQL injection attack occurs when an attacker is able to inject malicious code into a website's SQL query. They might be able to get access to critical data, as well as take control of the server.

  • Denial of service: An attack on a web server's availability is known as a denial-of-service attack. This is usually done by flooding the server with requests until it becomes overloaded and unavailable.

Web Server Penetration Testing Checklist

When planning a web server penetration test checklist, you should keep some essential things in mind. 

Here's a checklist:

  • Protocols: The first step is identifying which protocols are being used on the web server. This will help determine which attacks can be carried out and what data is transmitted.
  • Accounts: It is important to know who has access to the web server and what level of privileges they have. This data may be used to launch targeted assaults or gain unlawful access.
  • Files and Directories: You should also look at the files and directories stored on the web server. Both static and dynamic content is included. These may be used to launch assaults or obtain sensitive information.
  • Shares: In some cases, web servers may be configured to share resources with other systems. This can provide attackers with a way to gain access to the server or launch attacks against other systems.
  • Ports: A web server's ports are used for various reasons, just like any other computer. These need to be adequately secured to prevent unauthorized access.
  • Auditing and Logging: It is vital to have auditing and logging enabled on the webserver to detect and track any suspicious activity. This data may be used to study assaults or improve security procedures.
  • Server Certificates: In some cases, web servers may use SSL certificates for encryption. These need to be configured correctly to prevent man-in-the-middle attacks.

Top Tools for Web Server Penetration Testing

Several different tools can be used for web server penetration testing. Here are some of the most popular:

  • Astra's Pentest: Astra is a prominent internet security technology supplier with a seasoned team of penetration testers. Astra provides a comprehensive range of services, from vulnerability assessments to total-scale penetration testing. Its experienced staff has significant pen testing expertise. The professionals at Astra are trained in a specific approach and work with clients to ensure they are pleased with the outcomes. Astra's security specialists will work with you to assess and evaluate the risks to your web server and recommend mitigation techniques. Astra will then provide a thorough analysis, including suggestions for enhancing your web server security.

  • ZAP: The ZAP is a full-fledged penetration testing tool that can test the security of web applications. It includes features such as spidering web applications, detecting flaws, and launching attacks.

  • Metasploit: Metasploit is a free and open-source penetration testing platform that allows security experts to assess the security of their IT systems and applications. It's a comprehensive vulnerability assessment framework with many utilities and functions.

  • FFUF: The FFUF Directory Brute Force Tool is a powerful directory and file-finding tool for servers. This tool scans a website's list of popular directories and file names, then reports any that are discovered.


Web server penetration testing is a process of assessing the security of a web server in order to identify vulnerabilities that attackers could exploit. 

This type of testing can be used to assess the security of web applications, web services, and web servers. Many different tools may be used for web server penetration testing, and it's crucial to pick the right one for the task. In addition, a number of factors need to be considered when planning for a web server penetration test, such as protocols, accounts, files and directories, shares, ports, auditing and logging, and server certificates.


Published on Oct 28, 2022
Ankit Pahuja
Written by Ankit Pahuja
Ankit Pahuja is the Marketing Lead & Evangelist at Astra Security. Ever since his adulthood he began finding vulnerabilities in websites & network infrastructures. Starting his professional career as a software engineer at one of the unicorns enables him to bring "engineering in marketing" to reality. Working actively in cybersecurity for more than 2 years makes him the perfect T-shaped marketing professional. Ankit is an avid speaker in the security space and has delivered various talks at top companies, early-age startups, and online events.


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