Security Audit

Web Server Pentesting- What, Why, and How

Updated on: October 24, 2023

Web Server Pentesting- What, Why, and How

In today’s world, the performance and security of web servers are critical to the success of an organization. Web servers are a target of cyber attacks on a daily basis, and it is critical that they remain secure and protected at all times. 

While the specific attacks may change, the techniques used to gain access to web servers remain the same. These techniques are not easy to master and require specialized tools and knowledge.

This blog will look at the different aspects of web server penetration testing and why it is a critical practice. It will also look at how Astra Security can help you perform this penetration testing.

What is Web Server Pentesting?

Web Server Penetration Testing is a security assessment of a web server conducted to find vulnerabilities that attackers could exploit. It includes automated and manual server security testing, configuration, and architecture.

This type of penetration testing service is used to find flaws in the server software, hardware, or configuration that attackers could exploit. Web server penetration testing can also be used to test the security of the web server itself, as well as the applications and data hosted on the server.

A web server pentest aims to identify all security vulnerabilities and recommend mitigations to improve the security posture of the server.

Why is Web Server Penetration Testing Essential?

Organizations that rely on the internet for their day-to-day operations can’t afford to have their web servers hacked. That’s why web server penetration testing is essential. 

By conducting a web server pentest, organizations can identify and fix vulnerabilities in their web servers before attackers can exploit them. A web server pentest can also help organizations understand their web servers’ risks and develop strategies for mitigating those risks. 

Organizations that don’t pentest their web servers are leaving themselves open to attack. Hackers can exploit vulnerabilities to gain access to sensitive data, launch attacks against other systems, or disrupt services. By pentesting their web servers, organizations can reduce their systems’ risks and keep their data and operations safe.

Also Read: What is Penetration Testing (In Cyber Security)- Definition, Purpose and How to Perform

Best Practices for Web Server Security
Image: Best Practices for Web Server Security

What is the Difference Between Black Box and White Box Pentest?

There are two main types of pentesting: black box and white box. Black box pentesting is when the pentester does not have any prior knowledge of the system being tested. White box pentesting is when the pentester has complete knowledge of the tested system. 

Black box pentesting is more like a real-world attack because the attacker does not have any insider knowledge of the system. This makes it more difficult to find vulnerabilities, but it is also more realistic. 

White box pentesting is more like a system test because the pentester has complete knowledge of the system. This makes it easier to find vulnerabilities, but it is not as realistic. 

Which type of pentesting is better depends on the goal of the pentesting. If the goal is to find all possible vulnerabilities, then white box pentesting is better. If the goal is to find vulnerabilities that are more likely to be exploited in the real world, then black box pentesting is better.

Also Read: Top 5 Software Security Testing Tools [2022 Reviewed]

3 Common Vulnerabilities in Web Servers

Web servers are vulnerable to several attacks. Here’s an overview of the most common server vulnerabilities:

1. Unsecured Administrative Access

Most web servers come with an administrator interface that allows for managing the server remotely. However, these interfaces are often left unsecured, allowing attackers to gain control of the server if they can exploit the vulnerability. 

In many cases, the administrator interface is left open to the public internet, which makes it even easier for attackers to gain access.

2. SQL Injection Attacks

SQL injection is an attack that allows attackers to execute malicious SQL code on a web server. This code can be used to modify database content, delete data, or even gain access to sensitive information.

To protect against SQL injection attacks, web server administrators should ensure that their SQL databases are correctly configured and that all user input is carefully sanitized.

3. Denial of Service

A denial of service attack is a type of cyber attack that seeks to disable a server or a network by flooding it with requests, overwhelming its resources, and preventing it from being able to respond to legitimate requests. 

Denial of service attacks can be incredibly disruptive and may even render a server or network unusable. While denial of service attacks are not typically used to steal data or cause other damage, they can still be extremely costly in terms of the resources required to recover from the attack and the lost productivity and revenue.

Also Know: Penetration Testing Quote

How is Web Server Penetration Testing Performed?

Web Server penetration testing is a complex task, so it’s essential to understand how it is performed. We have divided the whole process into 5 different steps; let’s understand each one of them.

1. Identify the Scope of the Testing: This includes determining which systems and applications are in scope and what type of testing (e.g., black box, white box) is appropriate.

2. Perform Information Gathering: This step involves collecting information about the target systems and applications, such as IP addresses, operating systems, and application versions.

3. Identify Vulnerabilities: This step involves using various tools and techniques to identify system and application vulnerabilities.

4. Exploit Vulnerabilities: This step involves exploiting the identified vulnerabilities to access the systems and applications.

5. Perform Post-Exploitation Activities: This step involves performing activities such as privilege escalation and data exfiltration.

By following these steps, organizations can ensure that their web servers and web applications are secure and free from vulnerabilities.

Reading Guide: Top 5 Penetration Testing Methodologies and Standards

3 Open-Source Tools for Web Server Penetration Testing Testing

There are several open-source tools available for testing web servers. These tools can be used to test the security of web servers under various conditions.

1. ZAPOWASP Zap is a powerful tool that can test web applications’ security. It offers a wide range of features, including the ability to spider web applications, identify vulnerabilities, and launch attacks.

2. MetasploitMetasploit is an open-source penetration testing platform that enables security professionals to test the security of their systems and applications. It provides a comprehensive framework for security testing that includes a wide range of tools and capabilities

3. FFUF: The FFUF Directory Brute Force Tool is a powerful tool that can help you find hidden directories and files on a server. This tool works by accessing a list of common directory and file names on a website, then reporting any that are found. 

Also Read: 11 Top Penetration Testing Tools of 2022 [Reviewed] | API Penetration Testing: What You Need to Know

Astra Security: A Go-To Web Server Penetration Testing Company

Astra is a leading provider of web security solutions, and our expert team has extensive penetration testing experience. We offer a comprehensive range of services, from vulnerability assessment to full-scale penetration testing. 

Our approach is tailored to each client’s needs, and we work closely with them to ensure they are satisfied with the results. 

Our experienced security experts will work with you to identify and assess the risks to your web server. We will then provide you with a detailed report that includes recommendations for improving your web server security.

Why Choose Astra for Web Server Penetration Testing
Image: Why Choose Astra for Web Server Penetration Testing

It is one small security loophole v/s your entire website or web application

Get your web app audited with Astra’s Continuous Pentest Solution


Here at Astra, we know that many kinds of security threats can put your business at risk. Whether you run an eCommerce store, a portfolio of web properties, or an in-house solution for your business, you need to be sure that you have the best security in place to protect your company’s digital assets and your personal information from hackers.

Astra is the right fit for the job if you are looking for a web server penetration testing solution. Don’t hesitate to reach out to us; we’ll be happy to assist you.

What is the timeline for web pentesting?

It usually takes 4-7 days to complete penetration testing for a web server. It may take half as much time to complete the retests.

What is the cost of penetration testing?

Depending on the scope and the depth of pentesting the cost can vary between $100 and $500 per month.

How frequently should penetration tests be performed?

It is ideal to have at least one manual pentest a year along with quarterly vulnerability assessments.

Keshav Malik

Meet Keshav Malik, a highly skilled and enthusiastic Security Engineer. Keshav has a passion for automation, hacking, and exploring different tools and technologies. With a love for finding innovative solutions to complex problems, Keshav is constantly seeking new opportunities to grow and improve as a professional. He is dedicated to staying ahead of the curve and is always on the lookout for the latest and greatest tools and technologies.
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