It’s 2024, and for some reason, many businesses still underestimate the likelihood of an attack on their web apps. Ransomware damage costs are expected to skyrocket to 265 billion by 2031. Even the smallest error in your code can allow a nefarious hacker to wreak havoc.

Moreover, companies in several industries, such as finance and healthcare, must conduct pen tests to protect customer data following standardized regulations. Whether you’re required to conduct a pen test or not, consistent penetration testing is highly recommended to maintain the integrity of your web apps.

This article is your starting point for entering the world of web app penetration testing. Here are some of the key takeaways you’ll obtain from this article:

• What web application penetration testing is and why it’s important to your business
• The types of testing and steps involved in penetration testing a web app
• Pen testing requirements in your industry
• Questions to ask when interviewing a pen tester

Let’s begin.

What Is Web Application Penetration Testing In Cyber Security?

Web application penetration testing in cyber security is the process of analyzing web applications for security vulnerabilities. Penetration testers will employ a variety of tactics and tools to simulate an attack on your web application. The aim is to uncover weaknesses that a malicious actor can exploit, and in doing so, you’ll strengthen the security of your web application.

You can expect your pen tester to conduct a detailed and systematic overview of your web app from a hacker’s perspective. This mimics their adversarial approach.

Thus, the pen tester will attempt to bypass your security features, and test for vulnerabilities like SQL injection, cross-site scripting, and other common web security threats. The main goal is to find and resolve your application’s key security weaknesses before a hacker does.

Why Is Web Application Penetration Testing Important?

If you require a web application penetration test to comply with industry regulations, then there’s really no doubt. You need to get regular pen tests for your web apps if you want to continue doing business.

Furthermore, Milton Araujo, an EC council security expert says that Web apps have become the main target of attackers. Why is that? Web apps tend to contain the highest value information. As a consequence, their proliferation has been accompanied by an expanding cybersecurity perimeter.

So, given that web apps are one of the top attack vectors, penetration testing is one of your top defensive strategies. Penetration testing is unique in that it empathizes with attackers. Instead of merely scanning for weaknesses and taking preventative measures, it allows you to get to the root problems with your apps quicker. That can save you from a lot of damage to your organization’s reputation.

The 3 Types Of Penetration Testing: Picking The Right One

Picking the right type of web penetration testing isn’t black and white. In fact, it’s also gray.

Indeed, the three types of penetration tests are black box testing, white box testing, and gray box testing. They each have their own advantages and disadvantages, so let’s help you choose the right one.

1. Black Box Testing

In black box testing, the tester has no prior knowledge of the infrastructure or systems they are testing. This method simulates an external hack or cyber attack and is useful for understanding how an attacker would approach your system without inside information.

• Approach: Testers use publicly available information to find and exploit vulnerabilities, mimicking the tactics of a potential external attacker.
• Advantages: It can uncover weaknesses in your public-facing interfaces and reveal how an external attacker might penetrate your systems.
• Limitations: Without internal knowledge, you might not uncover deeper vulnerabilities within the system’s architecture.
• Best Suited For: Organizations looking to understand their vulnerabilities from an outsider’s perspective, such as testing the security of a website or web application.

2. White Box Testing

White box testing, also known as clear box or glass box testing, provides the tester with complete knowledge of the application or system. This includes access to source code, architecture documentation, and network information.

• Approach: Testers analyze the internal workings of the application, scrutinizing code and structures to identify any security flaws.
• Advantages: It allows for a thorough examination of your internal systems and can identify vulnerabilities that are not apparent from the outside.
• Limitations: This method can be time-consuming and requires skilled testers with a deep understanding of coding and system] architecture.
• Best Suited For: Organizations that need a comprehensive evaluation of complex applications or systems, often as part of a secure development lifecycle.

3. Gray Box Testing

Gray box testing is a hybrid approach that combines elements of both black box and white box testing. Testers have partial knowledge of the system, which might include some level of internal access, but not complete information.

• Approach: Testers utilize their limited knowledge to conduct a more focused and efficient assessment, bridging the external perspective of black box testing with some internal insights typical of white box testing.
• Advantages: It offers a balanced approach, uncovering both external and internal vulnerabilities, and is often faster than white box testing.
• Limitations: The partial knowledge might lead to missing some deep-seated issues that white box testing could uncover.
• Best Suited For: Organizations seeking a comprehensive understanding of their security posture without the resource intensity of white box testing.

Which Type Of Pen Testing Is Right For You?

White box testing is by far the most comprehensive, but it’s also the most time-consuming. If you have a small web app and a tight budget, then maybe it’s best to go with gray or even black box testing. On the other hand, organizations that have vital business processes integrated into their web apps are advised to spend as much as they can to protect them. In that scenario, white box testing is preferred.

How Penetration Testing Is Performed For Web Apps: Step By Step

The steps to pen testing are concrete, but the approach is somewhat flexible. Just as hackers can be erratic and unpredictable, a pen tester must be reflective and creative to emulate the behaviour of the world’s top hackers. After a complete analysis, a pen tester can bring order out of chaos, but their initial task is to bring about the chaos.

Here are the 6 steps to penetration testing for web apps.

Step 1: Planning & Reconnaissance

Firstly, the typical vulnerability scanner will figure out how your web app is supposed to work. They will spend a while toying around with your app seeing what it does and doesn’t do, its core features, and more.

Based on their knowledge of your app, the tester will brainstorm what kinds of attacks are possible. A typical example is when apps allow users to upload profile pictures, they are vulnerable to arbitrary file upload, which can be used to gain entry to your system.

Step 2: Vulnerability Scanning

While penetration testers try to stay away from overusing automated tools, vulnerability scanning is often automated. Employing tools like OWASP ZAP, Burp Suite, and Nmap, pen testers gather your web application’s known vulnerabilities. Many organizations will use vulnerability scans by themselves as a cybersecurity measure.

Step 3: Gaining Access Via Exploitation

With a full picture of your web app and its extant vulnerabilities, the pen tester will start breaking into your application. They’ll begin by testing each vulnerability one by one, moving down the list to see which exploits work and which don’t. Gradually, the tester can gain access.

Exploiting an app’s vulnerabilities often involves methodologies like SQL injection, cross-site scripting (XSS), and others. Once the tester gains access, they will also try to escalate their privileges to document the full extent of a potential breach. This helps them list which data and systems they can compromise.

Step 4: Maintaining Access

In the spirit of ethical hacking, the pen tester then simulates a persistent threat. That means they will try to remain in your system undetected by your system defenses for as long as possible, while continually gathering sensitive data from within your systems.

Step 5: Penetration Test Analysis

After a pen tester takes their breaches as far as they can, they’ll formulate a comprehensive report on your cybersecurity system. The notes they took during each process will guide their reflections. They’ll have recorded detailed logs, and taken inventory of your vulnerable systems. The report they eventually compile will prioritize vulnerabilities based on risk and recommend steps for mitigation.

Step 6: Remediation & Retesting

With every vulnerability laid out for all parties, the pen tester will often help you take measures to fix it. Fixes can include patching software, changing configuration settings, or improving security protocols. Following these fixes, you should also perform a retest to ensure that the remediations are effective and that no new vulnerabilities have been introduced.

What Information Does The Pen Tester Use To Make Their Findings?

When examining the target system, a pen tester needs many pieces of information to gain a comprehensive view. Here are the main pieces that are of interest to them:

1. System and Network Configuration

When the pen tester begins analyzing a web app, they often start with the basics: the system and network configuration. This includes:

• The network structure: internal and external networks, subnets, and DMZs.
• Server configurations, such as the extant server types, operating systems, open ports, services running, and software versions.
• The firewalls, if any exist, including their configuration and rule sets, alongside other security appliances.

2. Application Data

This goes back to that example we mentioned earlier regarding profile picture input. Your application’s input fields can easily be exploited based on how your app handles user input and data processing. This is where SQL injection and XSS vulnerabilities could lie. Your login systems and other authentication mechanisms pose a serious threat too.

Once a pen tester knows enough about your app, they might sit back and take a holistic view of your web application architecture, deciphering which front-end and back-end technology you use.

3. Code Analysis

In the case of a white box test, you would hand over your entire source code to the pen tester for review. They analyze your code to uncover security flaws, poor coding practices, and hardcoded sensitive information like passwords or API keys.

4. Network Traffic

One of your main concerns should be Data Transmission Security. Pen testers will analyze how data is transmitted over the network, looking for encryption flaws, insecure protocols, or data leakage.

HTTP Requests and Responses are another critical vector. Pen testers monitor web traffic to identify potential vulnerabilities or misconfigurations.

5. Existing Security Measures

Again, assuming a tester has white-box-level access to your systems and protocols, they can examine your security policies and procedures to find flaws. Moreover, they might check for outdated software or missing security patches. Clear evidence of weaknesses in your internal security policies.

6. User Behaviour and Privilege Levels

Once a pen tester breaks into your system, one of the first things they do to escalate is to identify privilege escalation opportunities. To do this, they usually find ways to manipulate User Role Definitions.

They might also examine Audit Trails and Logs to understand normal behavior patterns and detect anomalies or signs of previous breaches.

10 Helpful Penetration Testing Tools

The penetration tester needs the above information, from network configuration all the way down to user behaviour. To extract it, they often use a selection of the following tools.

We’ve discussed at length what types of penetration testing tools you could use in the linked article. Here’s a quick rundown:

1. OWASP ZAP (Zed Attack Proxy)

Information Analyzed: Identifies vulnerabilities in web applications.

Role in Pen Testing: It’s an open-source tool used for finding security vulnerabilities in web applications during testing. ZAP provides automated scanners as well as a set of tools that allow you to find security vulnerabilities manually.

2. Burp Suite

Information Analyzed: Analyzes web traffic to identify security issues and vulnerabilities.

Role in Pen Testing: This integrated platform is used for attacking web applications. It contains a variety of tools with powerful interfaces that can be used to speed up and automate the process of attacking an application.

3. Nmap (Network Mapper)

Information Analyzed: Discovers devices running on a network, identifies open ports, and detects security risks.

Role in Pen Testing: Primarily used for network discovery and security auditing. Nmap is useful for inventorying network devices, managing service upgrade schedules, and monitoring host or service uptime.

4. SQLMap

Information Analyzed: Automates the detection and exploitation of SQL injection flaws.

Role in Pen Testing: It provides support for database fingerprinting and data retrieval. You can also use it to access the underlying file system and execute commands on the operating system.

5. Metasploit

Information Analyzed: Helps in identifying security weaknesses and vulnerabilities.

Role in Pen Testing: A powerful tool for developing and executing exploit code against a remote target machine. It is used for penetration testing, exploit development and vulnerability research.

6. Hydra

Information Analyzed: Focuses on cracking login credentials to find password vulnerabilities.

Role in Pen Testing: Known for its fast and effective online password cracking capabilities. It can perform rapid dictionary attacks against more than 50 protocols, including telnet, FTP, HTTP, HTTPS, SMB, and more.

7. John the Ripper

Information Analyzed: Analyzes password strength and recovers lost passwords.

Role in Pen Testing: Primarily used for password cracking. This tool automatically detects password hash types and includes a customizable cracker.

8. W3af (Web Application Attack and Audit Framework)

Information Analyzed: Detects and exploits web application vulnerabilities.

Role in Pen Testing: It provides a penetration testing framework for securing web applications by finding and exploiting web application vulnerabilities. Great for internal penetration testing.

9. Ratproxy

Information Analyzed: Monitors web traffic to identify security loopholes.

Role in Pen Testing: A semi-automated, passive web application security audit tool. Used for analyzing web application traffic and identifying security weaknesses.

10. Wfuzz

Information Analyzed: Discovers common vulnerabilities such as SQL Injection, XSS, LFI, or RFI. Role in Pen Testing: A flexible tool for brute forcing web applications. Used for applications enumeration like parameters, forms, directories/files, and more.

How To Comply With Regulations In Your Industry: Pen Testing Best Practices

Aside from keeping your cybersecurity posture robust, penetration tests are a vital step in building trust in your industry. Regulations are often required, but pen testing is far more than just ticking a few boxes. If you do them properly and consistently, not only will you discourage cyber attackers from targeting your business, but you’ll also set a high standard for security within your organization. That can pay dividends for your brand’s reputation in the future.

Here are some best practices for penetration testing across all industries.

1. Regular Testing: Conduct pen testing routinely and after any major changes to your systems or applications.
2. Scope Definition: Clearly define the scope of penetration testing to ensure comprehensive coverage of all critical systems.
3. Expertise: Utilize experienced and skilled penetration testers for unbiased testing. Pen testers can help you at every stage of the process.
4. Remediation and Retesting: After identifying vulnerabilities, promptly remediate and conduct retests to confirm fixes.
5. Documentation and Reporting: Maintain thorough documentation of pen tests, findings, and remediation actions for audit purposes.
6. Employee Training: Regularly train employees on security awareness as human error often leads to security breaches.
7. Follow Cybersecurity News: Keep abreast of evolving cyber threats and update your pen testing strategies accordingly. This is important as common cybersecurity practices are rapidly becoming obsolete.

Now let’s look at some best practices and regulations you should observe in the following industries.

1. Financial Services

• Regulations: PCI DSS, GLBA, SOX
• Best Practices: Regular pen testing focusing on protecting financial data, transaction security, and customer privacy. Special attention should be paid to payment processing systems and compliance with PCI DSS requirements for regular testing.
• Compliance: Ensure encryption of data transmissions, secure handling of customer data, and regular audits.

2. Healthcare

• Regulations: HIPAA, HITECH
• Best Practices: Pen tests in healthcare should prioritize patient data security and integrity. Emphasis should be on securing electronic health records (EHRs) and ensuring that health information exchanges are secure.
• Compliance: Regularly update security measures to protect PHI, implement access controls, and conduct risk assessments as per HIPAA guidelines.

3. Retail

• Regulations: PCI DSS
• Best Practices: Focus on securing Point of Sale (POS) systems and e-commerce platforms. Regular testing for vulnerabilities in web applications and databases that store customer data is essential.
• Compliance: Adherence to PCI DSS requirements for secure payment processing and data protection.

4. Education

• Regulations: FERPA, COPPA
• Best Practices: Secure student data and educational records. Regular pen testing should be performed on student information systems and online learning platforms.
• Compliance: Ensure proper data management policies are in place and access to student records is controlled and audited.

5. Government

• Regulations: FISMA, GDPR (for European data)
• Best Practices: Focus on securing public data and internal communication networks. Pen testing should include social engineering aspects to test for data leaks and employee awareness.
• Compliance: Regular audits and assessments as per FISMA guidelines, with a focus on protecting sensitive government data.

6. Technology and Telecommunications

• Regulations: GDPR, CCPA
• Best Practices: Regular testing of network infrastructure and cloud services. Ensure the security of data centers and cloud storage, along with customer data protection.
• Compliance: Strong focus on data privacy, with adherence to GDPR and CCPA for customer data protection.

Penetration Testing Checklist: Everything You Need To Ask A Cybersecurity Expert

By now, you’re probably far more knowledgeable in the subject of pen tests than you were before. However, even if you have the skills to complete all the necessary tasks, they’re likely so time-consuming that attempting to execute a pen test in-house would be a huge drain on your resources.

That’s why it’s better to leave it to the pros. But before you do, you should develop some airtight criteria. A poorly done pen test could be more risky than not having one at all. Here is a list of questions you should ask a prospective pen tester when you interview them.

1. What is your testing methodology?
2. What kind of tools and technologies do you use?
3. Can you provide case studies or references?
4. How do you ensure the security of data during testing?
5. What is the expected timeline for the testing process?
6. How do you handle the discovery of vulnerabilities?
7. What kind of support do you offer post-testing?
8. Do you offer retesting services after remediation?
9. How do you stay updated with the latest security threats and vulnerabilities?
10. What are your qualifications and certifications?
11. How do you ensure compliance with relevant laws and regulations during testing?
12. What is your pricing structure?
13. How do you prioritize the vulnerabilities found?
14. Can you provide a sample report?

Secure Your Web Application With EliteSec

Now that you’re equipped with enough information to make the right decision about pen testing, we’d like to humbly put our name forward to conduct your next test.

With over 15 years of experience in cyber security, we’re well-equipped to handle cybersecurity projects of any size and complexity. Moreover, we pride ourselves on taking a collaborative approach with our clients. For us, that means answering every question they have about their cybersecurity posture truthfully and advising them about all the possibilities. Reach out to us for a free consultation to see what we mean.

If you want to further your knowledge, we have a lot more information about penetration testing best practices on our blog.