The Importance of Web Penetration Testing by@smoothmaruf

The Importance of Web Penetration Testing

Web penetration testing is a web assessment tool used by cybersecurity professionals to evaluate the integrity and effectiveness of existing cybersecurity tools. It's a self-appraisal test to assess exploitable loopholes in your computer system and network. Web-based apps can give adversaries access to personally identifiable information–PII– intellectual property, protected health information, and unwanted access to classified networks and resources. A successful web penetration test can reveal operational and organizational flaws that can be fixed before an attack occurs. Each test method functions based on client the test is for different clientele and security auditors.
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Abubakar Maruf

An adroit cybersecurity technical writer

One landmark growth of IT in the present digital landscape is the digitization of corporate organizations and business enterprises. Many organizations are approaching the internet to expand their market reach and ease of business. This has led to a new wave of doing business where business environments are carved out on the internet space–the web. With this, official and confidential documents about companies and clientele are uploaded to the internet for easy access when needed.

Although websites are generally protected from adversaries' exploitations, the presence and protection of confidential documents and intellectual properties require robust security. This security is aimed at repelling cyber-attacks or brute force from adversaries. Web penetration testing is one of the best tools used by security professionals to prevent this web intrusion.

What is Web Penetration Testing?

A pen test or penetration test is a modeled cyber-attack on your computer system to look for vulnerabilities that could be exploited. It's a self-appraisal test to assess exploitable loopholes in your computer system and network.

Web penetration testing is a web assessment tool used by cybersecurity professionals to evaluate the integrity and effectiveness of existing cybersecurity tools. It is a detailed security assessment used to detect risk factors that threaten existing cybersecurity implementations. A security assessment is executed to detect any vulnerability where a company's digital resources and networks are analyzed and scanned. Once vulnerabilities are detected, they are examined to determine if adversaries can exploit them through a penetration test.

Web penetration testing targets applications with web-based clientele, which covers most applications used by corporate organizations nowadays. Web penetration testing is a key component of any cybersecurity solution due to the wide adoption of web-based applications. This is because these web-based apps can give adversaries access to personally identifiable information–PII– intellectual property, protected health information, and unwanted access to classified networks and resources. This makes the threat of an attack on web-based customers' apps severe.

A frequent assessment of cybersecurity implementation is significant because web-based applications have increasing exposure to external attacks. How an organization responds to a successful penetration can reveal operational and organizational flaws that can be fixed before an attack occurs.

Fundamentals of Web Penetration Testing

Web penetration testing can be carried out using various methods and tools. Cybersecurity experts occasionally use spyware readily available to adversaries on servers in a sandbox environment. At times, the expert might perform penetration testing against active systems to evaluate prevailing weaknesses. It isn't easy to simplify the process of conducting a web penetration test due to the range of methods that can be used. Below are the three types of web penetration:

  1. Black Box This penetration test occurs when the cybersecurity expert–tester– has no foreknowledge of the target. During the penetration test, the tester will learn about the target, evaluate the systems and applications, look for flaws, and try to take advantage of those flaws. This black box test has the virtue of accurately simulating the process of a cyber-attack. The tester must engage the target like a malicious actor, revealing vital information. A black box penetration test has the drawback of taking a lot of time and effort. A black box test is broader in scope than others, but its disadvantage is that it is laborious and time-consuming.

  2. White Box

    In a white box test, the expert has foreknowledge of the network, company, and the weakness being investigated. White box penetrations are more prevalent than the black box tests and are used to examine the dangers posed by certain flaws. Since the tester already has access to available information about the target, white box tests are not as laborious as black box tests. Among the advantages of the white box are that they are concentrated and reveal a clear image of a detected vulnerability.

  3. Grey Box

    Like the combination of black and white colors results in grey, the grey box test combines black and white box tests. Here, the penetration expert typically has some knowledge about the target but not detailed information as in a white box test. The company may offer basic information that an attacker could typically obtain as a starting point for the test. Each test method is for different functions based on clientele and security auditors. Black box tests are customized to resemble an attack from adversaries, which can provide vital information about how a company's vulnerability is evaluated and exploited externally. In contrast, white box tests are thorough and can be used for penetration testing across all clients' web applications

    Methods of Web Penetration Testing

    Just as penetration tests differ, the methods of deploying these tests to assess systems also differ. This is why it is challenging to identify a general approach used by all and sundry. Instead, a general overview of web penetrating methods can describe the steps in deploying a web penetration test.

    The methods are reconnaissance, scanning, vulnerability assessment, exploitation, and access maintenance & reporting.

    i. Reconnaissance

    A web penetration test often starts with reconnaissance, where the tester learns about the target as much as possible. This covers details about their operations, systems, and organizational structure. Specifically, information like the network topology, user accounts, operating systems and applications, and other relevant data are gathered. This knowledge could provide insight into prospective attack vectors.

    Reconnaissance may be limited or even entirely ignored in web penetration testing types like the white box penetration testing, which is usually deployed with adequate knowledge of the target and all data pertinent to the test itself. In a black box penetration test, the reconnaissance phase is generally cumbersome and time-consuming because it may require various information gathering methods, including social engineering.

    Reconnaissance can be active or passive; if the information gathered was obtained by engaging the target system and such information is not available to the public, it is termed Active Reconnaissance. But if the information collected is already available to the public, it is termed Passive Reconnaissance.

    ii. Scanning

    The scanning phase is next after gathering the required information about the target's system. The scanning process involves examining the targets for vulnerabilities. There are numerous methods for doing this with different tools and strategies. This phase aims to identify any flaws that could potentially provide the tester access to secured systems or data.

    Usually, all open ports are identified and scrutinized because open ports are access points for adversaries. A vulnerability scan can also be performed as part of a thorough security assessment and serves the same purpose: to reveal any weaknesses. But it won't reveal the level of threat it poses until a penetration test is conducted.

    iii. Vulnerability Assessment

    This phase is similar to scanning but goes beyond it. Here, all data gathered during reconnaissance and scanning are used or combined to detect possible flaws and check if adversaries can exploit them. This assessment usually becomes significant when merged with other penetration testing phases.

    iv. Exploitation

    After assessing the flaws in the system, the tester will attempt to access systems or data via the flaws detected; this is known as exploitation. These flaws are often caused by inadequate patch management or outdated software, which gives adversaries seamless access to sensitive systems. Exploitation is attempted by concentrating on the server vulnerabilities, the tester attempting to access internet applications or classified data using tools that simulate actual attacks.

    Exploitation is very delicate because the system security will be bypassed, so the tester must take caution not to compromise the system. This phase cannot be limited to a single attack strategy or method. There are many different approaches and technologies used during the exploitation phase because so many applications, networks, and devices are connected to the internet.

    v. Access Maintenance and Reporting

    After exploitation has been deployed, maintaining access is the last step of a web penetration test before giving a detailed report. The pen tester might evaluate their ability to maintain access to important data or systems over time without being discovered. The tester may try to increase their access within the system during this phase to gain access to additional systems or data; this will help for broader evaluation. This phase provides crucial information about security responses, access control procedures, and system resilience during cyber-attacks.

    After completing all phases, the tester will prepare a report documenting the penetration test's procedures and results. The detailed report entails technical risks and impacts assessment, remedy, and professional recommendations. This is then used as a guide to improving the system's security architecture.

    Benefits of Web Penetration Testing

    • Preventing cyber-attacks
    • Preventing costly security incidents
    • Maintaining compliance with laws and regulations
    • Helps to comprehend the potential of cyber defense
    • Take away bargaining chips from rivals or competitors
    • Keeping cybersecurity professionals updated with the latest trends and techniques.


    System insecurity is the bane of many organizations and businesses banking on IT-related products and solutions.

    The method of deploying penetration testing may be necessarily comprehensive if each penetration test is conducted differently. How thorough or broad the testing will depend on which penetration test is done. Generally, the aim is to find exploitable vulnerabilities and address them to prevent cyber-attacks.

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