Web application penetration testing refers to testing the security of web application firewalls (WAFs), which filter, monitor, and block incoming and outgoing web service traffic, to make them as impenetrable as possible. To do it, penetration testers or pen-testers, for short, can attempt to breach a company’s applications, such as application protocol interfaces (APIs) and frontend and backend servers, to see if they have weaknesses that can be exploited through code injection attacks.

The results and findings of web application penetration tests are useful in fine-tuning WAF security policies and patching uncovered vulnerabilities.

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Web application penetration testing is a useful security measure because WAF data from logs can locate and exploit any application’s weak spots. WAF administrators can use this information to update configurations for added security.

Web application penetration testing also satisfies some security and auditing compliance requirements, such as the Payment Card Industry Data Security Standard (PCI DSS) and SOC 2.

But what does web application penetration testing entail?

5 Stages of Web Application Penetration Testing

Stage #1: Planning and Reconnaissance

As with any scientific or technical process, the first stage in web application penetration testing involves defining the test’s scope and goal. That includes identifying the systems that need to be tested and the methods to use. Observation or intelligence gathering comes next. The entire network should be scoured to pinpoint all vulnerabilities.

Stage #2: Scanning

After identifying all the applications and their weaknesses, learning how these can be targeted for exploitation comes next. That can be done using static and dynamic analysis.

Static analysis requires inspecting an application’s code to know how it behaves while running. It’s best to use tools that can scan an entire code in one pass. Dynamic analysis, meanwhile, refers to application code inspection while it’s running. As such, it provides a real-time view of how an application works.

Stage #3: Gaining Access

This stage of the web application penetration testing process is where pen-testers attack the applications. They typically launch cross-site scripting (XSS), SQL injection, and backdoor attacks to uncover a target’s weak spots. Exploiting these vulnerabilities typically involves escalating privileges, stealing data, intercepting traffic, and the like to see how much damage they can cause.

Stage #4: Maintaining Access

In this web application penetration testing stage, pen-testers determine if threat actors can use any of the vulnerabilities found to stay long enough in the target system to gain in-depth access. It primarily serves to mimic advanced persistent threats (APTs) that go undetected for months, allowing the bad guys to steal the most sensitive data.

Stage #5: Analysis

All of the web application penetration test results are compiled into a report that details the following:

  • Specific vulnerabilities the pen-testers exploited
  • Sensitive data the pen-testers accessed
  • The amount of time the pen-testers were able to stay in the system undetected

All the information is analyzed by security personnel so they can reconfigure the settings of WAFs and other application security solutions. Vulnerabilities are also patched in this stage to protect against future attacks.

Web application penetration testing can be done in several ways, as the next section shows.

5 Web Application Penetration Testing Methods

Companies can use various web application penetration testing tactics to ensure their networks are protected from all kinds of threats. These include the following:

External Testing

External web application penetration tests target Internet-facing assets, such as the web applications themselves, company websites, and email and Domain Name System (DNS) servers. The pen-testers’ goal? Gain access and extract valuable data.

Internal Testing

An internal web application penetration test is applied to applications that sit behind a company’s firewall. Pen-testers typically simulate an attack by a malicious insider. The usual scenario used is when an employee’s credentials are stolen through a phishing attack.

Blind Testing

In this kind of web application penetration test, all the pen-tester gets is the target organization’s name. As such, the company’s security personnel can get a real-time view of how an actual application assault would occur.

Double-Blind Testing

A double-blind web application penetration test does not give security personnel a warning regarding the simulated attack. As a result, the team won’t have time to beef up the network’s cybersecurity posture.

Targeted Testing

In this kind of web application penetration test, the pen-testers and security personnel work together. It is a valuable training exercise that gives security teams real-time feedback from hackers’ point of view.

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Web application penetration testing is a crucial security process that all companies with a web presence should engage in. It serves to prepare their security teams for attacks and ensures that none of their Internet-accessible assets are exposed.