Web application penetration testing: The beginner's guide

Web application penetration testing is the practice of simulating attacks on a system to gain access to sensitive data and determine if the system is secure. It remains an important part of a defence strategy, too. In 2023, over 26,0001 vulnerabilities were published by the National Vulnerability Database (NVD) - an increase of over 1,500 on the previous year. 

So, if you want to keep hackers out of your web application, security testing is the best approach to find vulnerabilities and configuration errors before they are exploited. Keep reading to find out how you can do it. 

What is web application pentesting? 

Web application pentesting is the process of examining a web application to find and fix security gaps. To ensure that the application can withstand any potential threats, Pen Testers run it through a series of tests using real-world scenarios.  

The primary goal of web application pentesting is to locate and document vulnerabilities in all sections of the programme (source code, database, back-end network). It's useful for prioritising the detected vulnerabilities and threats and the possible countermeasures against them. 

Web application pentests are often performed on the apps people can access via a web browser. This category includes the majority of software used in modern organisations. 

Through web-facing apps, hackers can get access to sensitive systems and assets, as well as personally identifiable information (PII), protected health information, and intellectual property. This increases the risk of an attack on a web-based client. 

However, that's not the only reason to implement web application pentesting. 

Why is web application pentesting important? 

Web application pentesting is an important part of any holistic security strategy. Here are four benefits: 

  • Satisfies compliance requirements - Compliance standards for industries often require certain security measures. Websites must also be compliant, and for risk management, their security must be checked and recorded. Web application pentesting makes it easier to meet these criteria. 
  • Tests digital infrastructure - The public may access infrastructure components like firewalls and DNS servers. Any modification to the underlying infrastructure increases the system's vulnerability to attacks. Pentesting can help uncover real-world threats that potentially compromise a web application.
  • Validates cybersecurity policies - If your company wants to build, document and uphold a culture of security, then you'll also need effective cybersecurity rules and procedures. And if you want to maintain the smooth running of your website's backend, it will also need strict standards for validating user input. Web application engineers can verify the accuracy of these guidelines. 
  • Identifies cybersecurity weaknesses - Outdated software and weak administrator passwords are examples of vulnerabilities that hackers can exploit. Spotting the damage is the first step toward fixing it. A pentest can reveal outdated software and poor permission settings. A cybersecurity risk assessment can detect non-technical concerns like insufficient user awareness training or the lack of an incident response strategy. All of these programmes aim to detect and address system flaws. 

What are the types of web application pentesting? 

Depending on your organisational requirements, you can conduct either internal or external web application pentesting. 

  • External pentesting 

External pentesting is all about simulating assaults on a website or web app that is already live on the internet. This type of hacking test uses the Black Box testing strategy, where a third-party pentesting service is often responsible for the attack. 

In this phase, the Pen Tester is typically given a list of the organisation's IP addresses and domain names. They'll then attempt to breach the target using only those two pieces of information, exactly as a hacker would in the real world. 

This type of testing involves evaluating servers, firewalls, and IDS to provide you with a complete picture of the state of your application's publicly accessible security measures. 

  • Internal pentesting 

Internal pentesting is performed on a web app because it is housed on the organisation’s private network. Therefore, it helps avoid assaults brought on by the exploitation of flaws in the organisation's firewall. 

Having an internal pentest of the web app is an often-overlooked step. Most people think it's impossible for a threat to operate within an organisation. This is no longer the case. When an online application has been externally compromised, it undergoes internal pentesting to determine the hacker's point of entry and follow their subsequent lateral movement. 

Learn more about external vs internal penetration testing and how they differ. 

How do you conduct a web application pentest? 

There are four phases of a web application pentesting. They are: 

Phase 1: Planning 

Several key decisions are made during planning that could affect subsequent steps of the pentesting process. The scope, duration, and participants must all be specified. Both the organisation and the web application pentesting service provider need to be on the same page about what they'll test. 

Before moving onto the testing phase, the first step is establishing the scope of the security assessment. Things like needing to test application pages and determining whether to test internally, externally or both, for example.

Establishing a timeframe is also essential. This speeds up the evaluation process, allowing you to put in place security measures sooner rather than later and better protect your application. 

Phase 2: Pre-Attack 

Reconnaissance work is completed at this stage, laying the groundwork for the following testing phase. Open Source Intelligence (OSINT) and other forms of publicly available information that can be exploited against you are a particular focus. 

In this stage of testing, activities like port scanning, service discovery, vulnerability analysis, and so on are conducted. You may use programmes like Nmap, Shodan, Google Dorks, dnsdumpster, and others for this purpose. 

Because of the widespread usage of social media within organisations, hackers may easily trick workers into giving up their social media passwords. So Pen Testers also use social engineering attacks, that aim to target companies with inadequate internal security measures. 

Phase 3: Attack 

The Pen Tester would attempt to take advantage of the flaws discovered in the previous step during the attack phase. Further, they may pinpoint and chart potential entry points for attackers. 

To compromise the host, a Pen Tester would delve deep into the functions of a web application during this phase. This might include phishing emails sent to employees or the organisation’s senior leadership, vulnerabilities in online applications, breaches in physical security, and so on. 

Phase 4: Post-Attack 

After the conclusion of the pentest, you'll recieve a comprehensive report. The format of this report changes depending on the organisation conducting the pentest or the nature of the application they're evaluating. 

Typically, a pentest report would detail any vulnerabilities that they had found, provide an explanation of those flaws, suggest solutions, and draw a conclusion. In addition, when an attack has been stopped, the Pen Tester will return the systems and networks to their original configurations. 

What are some top web application pentesting tools? 

Web application pentesting can be performed manually, automatically, or with a combination of the two. There are several advantages to automated pentesting, including increased speed, efficiency, and coverage. Manual pentesting is useful for locating Business Logic-related vulnerabilities. 

As a result, it aids in the elimination of false positives generated by automated scanning. It is usually recommended to conduct both to achieve the greatest possible results. 

Here are some top rated tools for web application pentesting: 

  • Cobalt 
  • Nmap Fingerprinting 
  • Shodan Network Scanner 
  • AppTrana 
  • Gobuster 
  • Invicti 
  • Burp Suite 

Conclusion 

Pentesting is a crucial part of the Secure Software Development Lifecycle (SSDLC) if you want to build safe, flaw-free web applications. It not only protects users from cyber threats like data theft and leaks, but also helps build trustworthy and legally compliant organisations. 

To know more about pentesting for information security compliance, check out our guide to ISO 27001 penetration testing. 

Schedule a free demo with our Infosec experts today to see DataGuard’s Infosec-as-a-Service solution in action. 

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