What to Know for Your First Web Application Penetration Test

web application penetration testing

Your library of cybersecurity measures and strategies should include web application penetration testing. It’s one of the most important security testing techniques for web applications. If you haven’t had one performed before, there are many things you should know about how they work, the benefits, and best practices for choosing a testing partner.

These tests can help you quickly and accurately identify and remediate threats before a cybercriminal takes advantage of any vulnerabilities. While web application penetration tests are a common and standard practice, that doesn’t mean there aren’t a lot of factors to consider. In this post, you’ll learn everything you need to know for your first web application pen test.

What Are Web Application Penetration Tests?

Web application pen tests are simulations conducted by ethical hackers in an attempt to access sensitive data. In this process, testers assess the architecture, design, and configuration of your web applications, which consists of anything delivered over the internet through a browser interface. Since these are public-facing, web applications are a favorite target for hackers. Thus, their risk priority is high.

These tests aim to find the vulnerabilities before the hackers do. Pen testing is different from vulnerability scanning, however. They are both vital to cybersecurity, but vulnerability scanning isn’t a substitute for pen tests.

Vulnerability Scanning vs. Pen Tests

As you design your pen test strategy, ensure you understand how they complement vulnerability scanning. Vulnerability scans alert you of known weaknesses in an application, followed by methods to improve or resolve them. So, in this tactic, you confirm that patches are installed, and configurations are correct.

A pen test is a simulated hack that provides insights from the cybercriminal perspective, using the same tricks that real threat actors use. Pen tests are preventative cybersecurity, whereas scans are a detective control mechanism.

Before initiating testing, it’s a good idea to differentiate between the two. This positioning also highlights the importance of and need for pen tests.

Why You Need to Conduct Penetration Testing

Pen testers become your covert detectors to identify what’s exploitable. They serve a pivotal role in a proactive cybersecurity strategy. They are valuable because they:

  • Detect both known and unknown vulnerabilities and prioritize them for remediation
  • Check the effectiveness of security policies
  • Test the elements that are public-facing, like firewalls, routers, and DNS servers, to evaluate your infrastructure
  • Define the most vulnerable route for an attack to occur
  • Find loopholes that can result in a data breach so that you can address them
  • Support compliance programs and adherence to regulations for industries like healthcare and banking

Next, we’ll look at where to start. Your first decision will be the level of access you provide the testing team.

Web Application Pen Tests: Black, Gray, or White Box

As you begin planning, you’ll need to decide on the access level. There are three options:

  • Black Box Penetration Testing: In this approach, testers have no prior knowledge of the target system’s internal structure. It’s the most realistic simulation, as testers play the role of hackers seeking to exploit web applications by any means.
  • Gray Box Penetration Testing: In this scenario, there’s more context. Testers gain some general information about a target system. Those items can include algorithms, codes, or data structures. You can also provide them with credentials to emulate an inside attack from an authenticated user on your application. Often, organizations opt for Gray Box for specific use cases around the security of an application. Many gray box tests also include a black box, unauthenticated test.
  • White Box Penetration Testing: With this access level, testers can access systems and artifacts like source code and containers. Additionally, they may have the ability to access servers running the system.

For first-timers, Black or Gray Box testing is where to start. Black Box, as noted, is a real-world simulation. Understanding the threat landscape from this perspective is a foundational building block. After learnings and remediation, move on to Gray and then White Box.

The next thing to discuss is web penetration testing methods.

Web Application Pen Testing Methodologies

The methodology describes the set of security industry standards that guide the testing. Determining which is the best fit depends on the use cases and types of applications. You should talk about these with the testers to hear their recommendations. The most common methodologies include these standards.

OWASP (Open Worldwide Application Security Project) Top 10

The top 10 is a consensus on the most critical risk to web applications. It’s widely used and includes these categories:

  • Broken Access Control
  • Cryptographic Failures
  • Injection
  • Insecure Design
  • Security Misconfiguration
  • Vulnerable and Outdated Components
  • Identification and Authentication Failures
  • Software and Data Integrity Failures
  • Security Logging and Monitoring Failures
  • Server-Side Request Forgery (SSRF)

OSSTMM (Open Source Security Testing Methodology Manual)

The OSSTMM provides a methodology for security testing that’s consistent and repeatable. It’s open source so many testers can contribute to the output. This option is used primarily for testing against industry or regulatory requirements. Its framework provides instructions for testing operational security.

PTF (Penetration Testing Framework)

PTF is a database of scanners, tools, and exploits that penetration testers can use. It’s a Python script that enables testers to keep their toolkit current. It can do retrieval, compilation, and installation of tools.

ISSAF (Information Systems Security Assessment Framework)

The ISSAF is another resource for pen testing. It includes guidance across numerous areas. Its intent is to evaluate application controls and has three phases and nine steps. It basically gives an ethical hacker a model to follow when conducting a pen test.

PCI DSS (Payment Card Industry Data Security Standard)

The PCI Security Standards Council has its own pen test framework for the industry. It includes pen testing components, methodologies, and reporting guidelines. For those in this vertical that must conduct pen tests, this framework is necessary.

There’s still more to know about web application pen tests. Next, we’ll cover the general steps.

Web Application Pen Tests: Seven Steps

These are the seven steps you can expect your pen-testing partner to follow. This is the penetration testing methodology that Blue Goat Cyber uses. Any reputable penetration testing company should follow something similar. You’ll want to have a conversation about this to ensure alignment of objectives and requirements.

Step One: Planning and Preparation

The first step occurs before the test begins. It can include a variety of actions for testers to define their attack strategy. Those may involve:

  • Defining the scope
  • Ensuring testers have information if provided
  • Understanding the environment

Step Two: Reconnaissance/Discovery

Next, the testers investigate the target system to collect data. Scanning of the applications usually occurs in this step. This phase is about building the attack strategy.

Step Three: Vulnerability Enumeration/Analysis

In this step, testers assess vulnerabilities. They are using a variety of tactics to detect weaknesses. The goal is to tie threat sources to a vulnerability for later prioritization.

Step Four: Initial Exploitation

At the conclusion of step three, testers then move to exploitation. Testers attempt to establish access to applications using the vulnerabilities discovered.

Step Five: Expanding Foothold/Deeper Penetration

If the tester succeeds with the first exploitation, they will try to escalate this further. The deeper the person can go, the more insights they can gather on all the weaknesses.

Step Six: Cleanup

Once the tester has exploited and detected as much as possible, it’s time for them to leave. They leave the application and return it to its former state.

Step Seven: Report Generation

The final phase is the delivery of the report. This analysis would include all details on vulnerabilities, their priority, and how to remediate these items. Keep in mind that not all reports are the same. Often, they can be overly technical and use complex language. It’s an essential thing to evaluate when choosing your pen test firm.

Choosing a Web Application Testing Provider: What to Evaluate

Finding a reliable, experienced, and reputable partner for pen testing requires some research and comparisons. Since it’s your first time, it can be overwhelming. Here are some key things to remember during your assessment:

  • Training, experience, and credentials. You want to work with a firm with extensive experience and can demonstrate that. In terms of credentials, those that matter in pen test expertise include CISSP, CSSLP, OSCP, ECSA, LPT (Master), and CEH.
  • Automated vs. human-led. There are many great pen test tools, but organizations that automate all aspects won’t deliver the best results, as too many false positives and negatives happen. Human-led testing is always going to be the best option.
  • Methodology expertise. There are lots of methods to pen test, as we’ve reviewed. Testing specialists should have one that’s proven and that they continue to improve.
  • Inclusion of remediation validation tests (RVTs). After you deploy fix actions, your pen testers should run an RVT so you know it was accurate.
  • Reporting that’s concise and clear. The reports don’t have to be long. They do need to be actionable, prioritized, and straightforward.
  • Reputation. A professional cyber firm will have strong respect within the industry, which demonstrates reliability and honesty.

Initiating your first pen test is a critical occurrence for your organization. Getting it right starts with education, guidance, and support. If you’re ready to learn more, contact us today for a discovery session.

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