Web Application Penetration Testing: Why It’s Important

by | Sep 25, 2022 | Penetration Testing

Security experts often employ web application penetration testing to examine the reliability of web-facing cyber assets and systems. Web application penetration testing is required to identify risk variables linked to critical cybersecurity system initiatives. Despite the need to do frequent penetration tests, many individuals outside of the cybersecurity sector do not understand their significance. We will define web application penetration testing in this post and look at web application penetration testing techniques, and talk about why it is a crucial part of any security program.

Web Application Penetration Testing: What is it?

Cybersecurity experts utilize web application penetration testing to evaluate the effectiveness of current cybersecurity initiatives. For your team to handle threats and vulnerabilities, a thorough security assessment should include penetration testing. An organization’s cyber assets and systems are analyzed and scanned for vulnerabilities during a security assessment. Through penetration testing, vulnerabilities are examined to see if bad actors may use them to their advantage. Penetration testing attempts to determine if a vulnerability is genuine and the likelihood for it to be exploited.

Applications with browser-based clients are mainly targeted by web application penetration testing. The great majority of apps utilized in modern enterprises fall within this category. Web application penetration testing is a critical component of any current cybersecurity solution due to the widespread usage of web-based applications. Web-facing apps can potentially provide bad actors access to sensitive assets and systems, personal identifiable information (PII), protected health information, and intellectual property (IP). The danger of an attack on a web-based client is thus severe.

In contrast to physical systems and assets, web-based applications are more vulnerable to outside threats. As a result, it’s crucial to routinely evaluate a cybersecurity solution to see whether any weaknesses may be exploited. Web application penetration testing may also assess the efficacy of a current cybersecurity posture. How a company responds to a successful infiltration may reveal organizational and operational flaws that can be fixed before an attack occurs.

Basics of Web Application Penetration Testing

A cybersecurity expert must launch an attack against a web application to do web application penetration testing. This attack aims to try to access systems that an attacker shouldn’t be able to. The penetration tester will try to use that access to penetrate the system further after they have achieved entry through a vulnerability. In other words, a web application penetration test entails a benign actor attacking a system like a malicious actor.

Web application penetration testing may be carried out in many ways and using various tools. On systems in a sandbox environment, a cybersecurity expert could sometimes try to employ hacking tools accessible to hostile actors. In other situations, a cybersecurity expert could do penetration testing on active systems to evaluate prevalent real-world vulnerabilities. It isn’t easy to simplify the process of conducting a web application penetration test due to the range of methods that may be used. We’ll break down the web application testing technique rather than try to.

Web application penetration testing
BurpSuite Tool

There are primarily three methods used to perform web application penetration tests. These exams go by the names black box, white box, and grey box. Although each of these penetration test methodologies has benefits and drawbacks, they all aim to achieve the same objective.

White Box

When the penetration tester has no previous knowledge of the target, a black box web application penetration test is conducted. During the penetration test, the tester must learn about the target, evaluate the systems and applications, look for vulnerabilities, and take advantage of such weaknesses. A black box test has the benefit of accurately simulating the progression of a malicious attack. The tester will have to approach the target in the same manner as a malicious attacker out of necessity, which might provide important information. A black box penetration test has the drawback of taking a lot of time and effort. A black box test is broader than a white or grey box test.

Black Box

When performing a white box test, the penetration tester is familiar with the organization, system, and vulnerability they are testing. White box penetration testing is far more frequent than black box tests and is used to examine the dangers of particular vulnerabilities. Since the tester already has quick access to knowledge regarding the test target, white box tests lack the thorough reconnaissance necessary for a black box test. Because white box tests are concentrated, targeted penetration testing that may provide a clear image of a discovered vulnerability are helpful.

Gray Box

Both white and black box test components may be found in a grey box test. The penetration tester will normally have some knowledge of the target during a grey box test but not the amount of specificity that you could see during a white box test. The client may provide information that an attacker might typically get as a starting point for the test.

Clients and security assessors employ many web application penetration test methods to accomplish various tasks. White box tests are thorough and may be used to do penetration testing on all of a client’s web apps. Contrarily, black box tests are set up to seem as if an evil actor was carrying them out, and they may provide crucial information on how an organization’s vulnerabilities and weaknesses are evaluated and exploited from the outside.

The testing technique that security experts employ to evaluate web systems varies, just as there are variances between the many penetration tests. As a result, it is difficult to identify a single, universally accepted technique. Instead, it may be beneficial to describe the procedures required in web application penetration testing with a broad summary of the method. Web application penetration testing consists of four main stages. These include access reconnaissance, scanning, exploitation, and maintenance.


A web application penetration test often starts with the reconnaissance phase. The tester will learn as much as possible about the target. This covers details about their operations, systems, and organizational structure. Information collecting may be limited or skipped altogether in some web application penetration testing situations. This is often true for white box penetration testing, frequently carried out with a full-field view of the target and any data pertinent to the test itself. The reconnaissance phase of a black box penetration test will be drawn out and time-consuming, and it may entail social engineering or other types of information gathering.

Shodan Recon OSINT Tool
Shodan OSINT Tool


The second step of a web application penetration test entails system scanning for the target. The list of systems to target and their corresponding IP addresses may be acquired by testers or made available during the first step. Assessing these cyber assets for vulnerabilities is the process of scanning. There are several ways to do this, as well as numerous tools and strategies that may be used. The scanning step aims to identify flaws that might provide the tester access to secured systems or data. A vulnerability scan is performed as part of a thorough security assessment and serves the same purpose.

BurpSuite Scanning Module
BurpSuite Scanning


An attempt is made to access systems or data during the exploitation phase of a web application penetration test using the vulnerabilities found during scanning. By concentrating on server-side vulnerabilities, the tester may try to access web-based apps or sensitive data during the exploitation phase of a web penetration test. These flaws are often caused by inadequate patch management or outdated software, which gives hostile actors simple access to delicate systems. Particularly when discussing web-based attacks, the exploitation phase cannot be reduced to a single attack strategy or vector. Many different approaches and technologies are used during the exploitation phase since many apps, systems, and devices are linked to the internet.

SQLMap Tool to Exploit SQL Injection
SQLMap to Exploit SQL Injection

Maintain Access

After an attack payload has been released, sustaining access is the last step of a web penetration test. The penetration tester could evaluate their ability to continue having access to vital data or systems over time without being discovered. Penetration testers may not always replicate the data extraction and attack obfuscation characteristic of malicious attacks. The penetration tester may try to increase their privileges inside the system during this phase to access other systems or data. When an attacker has penetrated your network, the last round of penetration testing may provide crucial information about security responses, access control procedures, and system resilience.

The attack pattern that a hostile actor would use to access protected data or systems may be precisely tracked by penetration testing for web services, as is evident from the approach described above. The stages of a penetration test replicate how someone unfamiliar with a company or network might behave. The following approach must be comprehensive since each penetration test may be conducted differently. Whether a penetration test is a white, black, or grey box test and whether the tester has in-depth knowledge of the target systems might affect this. The ultimate objective of a penetration test is to identify a weakness in a system, exploit that weakness, and demonstrate the repeatability of the attack. As a result, penetration testing is a crucial yardstick for gauging how vulnerable a web-based system or application is to outside attacks.

Reverse Shell for penetration test
Metasploit Reverse Shell

Why Does Web Application Penetration Testing Matter?

Some businesses could question the value of web application penetration testing. The truth is that companies now face a far broader range of risks than they had in the past. This is especially true for gadgets and programs with an online connection. Understanding and defending how devices and applications interact with one another on internal networks is necessary, and hardening them against external attacks is necessary. The prevalence of personal devices used for routine corporate operations raises the risk factor for today’s enterprises even more.


A web penetration testing service is an essential tool that businesses may employ to guarantee the success of their cybersecurity deployment. A security assessor may establish whether the web application vulnerabilities identified during a security scan are genuine via web penetration testing. A penetration test will assist in determining the risk involved with a vulnerability if it can be exploited in the real world. Web penetration testing is sometimes difficult and time-consuming, but it’s still essential to evaluate how well your present cybersecurity posture is working. It is crucial to remember that web application penetration testing operates by evaluating your current cybersecurity efforts, which is why its significance cannot be overstated. Penetration testing does nothing more than confirm what you already know if your cybersecurity is shoddy. To succeed, penetration testing must be performed in concert with other technologies that cybersecurity experts use to thoroughly evaluate every aspect of your organization’s cybersecurity. Consider hiring a third-party security assessor, like Artifice Security professionals, to conduct a thorough security audit of your cybersecurity solutions if you are unsure if your cybersecurity is sufficient for your firm’s risks. Before a bad actor launches an attack, you may find and resolve security vulnerabilities, risks, or defects using independent experts to evaluate your cybersecurity efforts and posture. Additionally, enterprises can maintain the proactive cybersecurity posture required in today’s environment to fight against sophisticated, persistent attacks thanks to the continuous data protection provided by third-party security assessors.

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