What is penetration testing?

In today’s digital age, cyberattacks are becoming more prevalent, with hackers discovering new ways to attack using the most secure systems. This rise of cyberattacks popularized the concept of penetration testing: an active security technique in which an honest security professional attempts to break into your systems before an attacker does.

Penetration testing is a complete procedure in which cybersecurity professionals reproduce real-world attacks on your computer systems, networks, and web applications, all with your consent and in a controlled environment. This technique has grown in importance as organizations meet more security risks, with regular testing helping identify and correct vulnerabilities before hackers use them.

“Penetration testing is not just about finding vulnerabilities—it’s about understanding how those vulnerabilities could impact your business in the real world,” says Chris Nickerson, a Red Team Security expert and founder of LARES Consulting.

While standard security testing searches for known flaws, penetration testing goes beyond that by actively attempting to exploit these flaws.

Penetration testing in the testing process

Penetration testing is the final step in the security testing process, following basic security scans and risk evaluations. While standard security testing searches for known flaws, penetration testing goes beyond that by actively attempting to exploit these flaws. The process of penetration testing is meant to find all the potential points of risk in your system before a Bad Actor exploits them.

Who does it?

Penetration testing is frequently carried out by qualified security professionals known as “ethical hackers.” These individuals combine extensive technical knowledge with innovative problem-solving abilities. They can be internal security teams or external consultants, each providing their perspective to identify dangers you may have missed.

What are its goals?

The main goals of penetration testing include:

1. Identifying security weaknesses—Find vulnerabilities in your systems before real attackers do, allowing you time to address them.
2. Testing your defense systems—Check that your security measures perform as expected in real-world attack scenarios.
3. Meeting compliance requirements—Help your firm comply with security requirements and regulations by demonstrating effective security measures.
4. Improving incident response—Test your team’s ability to recognize and respond to security breaches, which will help them prepare for real-world attacks.

Types of penetration testing

“The key to good security testing is knowing that different attack surfaces require diverse testing methods. One size does not fit all in penetration testing,” says Dr. Charlie Miller, a former National Security Agency hacker and well-known security expert.

Network penetration testing

Network penetration testing involves a security specialist investigating all possible weak spots or entry points of your office network. Whether it is an old wireless network that is not secure, a firewall that has a blind spot, or others, network penetration testing makes sure your system is protected against potential attacks.

Web application testing

This is similar to assessing the security of your online business or bank website. Testers attempt to get into your website by using techniques such as logging in as another user, stealing client information, or manipulating prices in your online store.

For example, they may attempt to adjust the price of a product in your shopping cart from $100 to $1 or view other customers’ orders. That helps in identifying weak points before actual attackers can exploit them to steal data or money.

Mobile application testing

This focuses on testing apps for phones and tablets. Testers determine if your mobile app manages user data safely, such as passwords and credit cards. For example, they check to see if the app accidentally saves passwords in plain text, where anyone can see them, or if data is stolen when a user makes a purchase. They also ensure that the app is secure even when linked to public WiFi in coffee shops.

Social engineering testing

This checks for human security by tricking staff into making security errors. Testers may send bogus emails claiming to be the CEO and requesting passwords, call pretending to be IT assistance or attempt to enter the office by following an employee through the door.

For example, they could send a bogus urgent email to employees requesting that they log into a duplicate of your company’s website to obtain their passwords. This helps identify which staff members require more security training.

Physical penetration testing

This includes assessing your actual building security. Testers attempt to enter restricted places such as server rooms or offices. They could try to sneak in by following personnel, picking locks, or pretending to be delivery people.

For example, they could leave a USB drive in the parking lot and observe whether employees plug it into corporate computers, or they could try to gain access to the server room by acting as maintenance staff. This aids in detecting vulnerabilities in your physical protection before real thieves can exploit them.

How does penetration testing work?

“A thorough penetration test should mirror real-world attack scenarios as closely as possible,” emphasizes Dave Kennedy, founder of TrustedSec and creator of the Social-Engineer Toolkit.

The penetration testing process follows a structured approach that helps ensure nothing is missed during the security assessment:

Planning and monitoring

Testers begin by gathering all available information about your systems, much like a detective researching a case. They examine your network topology, identify the systems you’re using, and decide which regions require testing.

This step also includes establishing specific goals, timetables, and engagement rules, which define what testers can and cannot do throughout their evaluation. They may even look at your company’s public information and social media to identify potential weaknesses.

After the planning is completed, testers use specialized tools to examine your systems for potential vulnerabilities.

Examining the system

After the planning is completed, testers use specialized tools to examine your systems for potential vulnerabilities. Imagine a doctor utilizing an X-ray machine to look for issues. They investigate how your network responds to various types of connection attempts, determine which services are running on your systems, and uncover any security flaws.

This phase includes static analysis (evaluating systems while they are not running) with dynamic analysis (testing systems while they are running).

Gaining access

Now comes the actual “testing” phase. Using the information acquired, testers attempt to exploit the vulnerabilities they have identified. They might try password cracking, exploiting software flaws, or deceiving security systems.

Simulating persistent threats

After getting access, testers attempt to stay inside your systems for a long period. This helps them understand whether your security staff can discover unwanted access and how long it will take.

They may attempt to install hidden software or set up secret user accounts. This phase shows how much damage a real attacker could do if they got into your systems and were not detected quickly.

Analysis and reporting

Finally, testers compile everything they’ve found into detailed reports. These reports include vulnerabilities they discovered, how they managed to exploit them, what sensitive data or systems they accessed, and clear step-by-step recommendations for fixing each problem.

Benefits of penetration testing

“The true value of penetration testing lies not just in finding vulnerabilities, but in understanding how they could impact your business,” says Mark Burnett, a cybersecurity researcher and author.

1. Early detection of security weaknesses: Find and repair vulnerabilities before attackers exploit them. This approach enables you to correct security gaps before they become major breaks, saving both money and reputation.
2. Real-world risk assessment: Develop a solid awareness of your current security concerns. Practicing genuine attacks allows you to see exactly how attackers can target your systems and the damage they could cause.
3. Compliance validation: Regular testing ensures compliance with regulations such as GDPR, HIPAA, and PCI DSS while also providing evidence to demonstrate your security efforts.
4. Improved security awareness: Help your staff have a better understanding of security threats and responses. When employees observe actual examples of security flaws, they are more likely to comply with security rules and spot possible threats.
5. Cost-effective security: Early detection and resolution of vulnerabilities can help to avoid costly security breaches. The expense of frequent testing is significantly less than the potential financial impact of a serious security breach, which includes fines, legal fees, and lost revenue.
6. Enhanced customer trust: Show customers that you care about their security. Regular testing indicates your dedication to preserving client data, which can help you gain a competitive advantage and develop customer relationships.
7. Better decision-making: If you gather data that guides you clearly about the security investments, testing results assist you in prioritizing security spending and focusing resources on the most critical areas, ensuring that your security budget is spent efficiently.

Challenges of penetration testing

“Every penetration test faces unique challenges, but the key is finding practical solutions that balance security needs with business operations,” notes Kevin Johnson, CEO of Secure Ideas.

1. Resource intensity: Complex testing demands a large amount of time and skill, which can put a strain on your resources. Organizations frequently struggle to strike a balance between extensive testing and preserving normal business operations, especially with limited security personnel.
2. Risk of system disruption: Testing can accidentally disrupt routine corporate operations or harm systems. Even well-planned tests might have unexpected effects on production systems, requiring careful coordination and backup procedures.
3. Incomplete coverage: It is challenging to test every possible scenario, so certain vulnerabilities may remain uncovered. Because IT systems are continually changing, even thorough testing may overlook some security flaws.
4. Keeping up with new threats: New attack strategies arise regularly, requiring the ongoing upgrading of testing procedures and tester knowledge.
5. Timing and scheduling: Determining the optimal time for rigorous testing without disrupting corporate activities can be challenging. Organizations must strike a delicate balance between security, business continuity, and customer service.

Tools for penetration testing

Modern penetration testing relies on various specialized tools. Here are the key tools you should know about:

Nmap (Network Mapper)—Think of Nmap as a digital explorer for your network. It helps you discover what devices are connected to your network, what services they’re running, and what potential entry points exist for attackers. This tool is particularly valuable because it can quickly scan large networks and provide detailed information about each discovered device, making it essential for the initial phases of security testing.

Wireshark—This tool is like a microscope for your network traffic. It captures and analyzes the data flowing through your network in real time, helping you spot suspicious activities, troubleshoot network problems, and identify security issues. Security professionals use it to understand how their applications communicate and to detect any unusual or malicious network traffic patterns.

Metasploit—It serves as a complete toolkit for testing security vulnerabilities. It includes a collection of tested exploits, a database of known vulnerabilities, and tools for developing new security tests. This platform helps security teams verify if their systems are vulnerable to specific attacks and understand how attackers might exploit these vulnerabilities.

Burp Suite—This tool specializes in testing web applications for security weaknesses. It acts as a security checkpoint between your browser and web applications, allowing you to intercept, analyze, and modify the traffic between them. Burp Suite is particularly useful for finding common web vulnerabilities like SQL injection or cross-site scripting attacks.

Kali Linux—An entire operating system built specifically for security testing, it comes pre-loaded with hundreds of security tools, making it a one-stop shop for penetration testers. This system includes everything from password crackers to wireless network testers, making it an essential platform for security professionals.

Conclusion

The success of your security systems is only as strong as your penetration testing strategy- without engaging in thorough testing of potential weak spots in your security systems, you and your team cannot provide the proper defenses against cyberattacks. With knowledge of the testing method, its benefits, and problems, you can make more educated judgments about implementing penetration testing into your security plan.

This post was written by Gourav Bais. Gourav is an applied machine learning engineer skilled in computer vision/deep learning pipeline development, creating machine learning models, retraining systems, and transforming data science prototypes into production-grade solutions.