What is a Penetration Test and How Does it Work?

July 14, 2020 Eric Dosal Eric Dosal

6 Min Read

Cybersecurity companies offer a wide range of services to their customers to prevent the majority of cyberattacks from succeeding. One of the most common services offered by managed security service providers (MSSPs) is penetration testing (also known as “pen tests”). Since their inception, penetration tests have become a core cybersecurity service, helping organizations of all sizes and industries identify potential weak points in their network security architecture so they can be fixed.

However, what is a penetration test, exactly? And, how do pen tests work?

For those who are curious about penetration testing and how modern cybersecurity companies handle this service, here is a brief explanation of the basics:

What is a Penetration Test?

The SANS Institute provides a definition for penetration testing in their Conducting a Penetration Test on an Organization whitepaper: “Penetration tests are a great way to identify vulnerabilities that [exist] in a system or network that has… existing security measures in place. A penetration test usually involves the use of attacking methods conducted by trusted individuals that are similarly used by hostile intruders or hackers.” In short, pen tests are a critical vulnerability management tool that help uncover weaknesses in a cybersecurity architecture by using simulated attacks carried out by trusted people.

Penetration tests have been a critical part of cybersecurity for decades—ever since government and business organizations first realized that the growing interconnectivity and remote communications of computers were vulnerable to being accessed illicitly. In fact, according to the Infosec Institute, “since the mid-1960s, and with increasing sophistication, white hat testers have worked to ensure that computer systems remain secure from hackers.”

How Does a Penetration Test Work?

Penetration tests can work in different ways—there is no one comprehensive testing method that everyone uses. Part of this is because cyber threats are continuously evolving—and pen tests need to simulate whatever attack methods the organization is likely to encounter.

Some of the “broad strokes” of a penetration test include:

  1. Assigning a person or team to act as “white hat” hacker(s) to conduct the test at a randomized date and time.

  2. Vulnerability management team members scanning the IP addresses of different assets on the network to identify assets using services or operating systems with known vulnerabilities.

  3. The penetration testing team conducting a series of simulated attacks against the network using different attack methods. These attacks may target known vulnerabilities from the preliminary scan.

  4. The organization attempting to contain, stop, and investigate the attack as if it were a real one (depending on how the attack is conducted, the cybersecurity team may not know it is a pen test instead of a real attack).

It is important for the pen test team to be careful when conducting the test. If the test is carried out poorly, it could cause actual damage to the target systems—resulting in congestion or outright system crashes for some network assets.

Why Run a Penetration Test?

Right after “what is a penetration test and how does it work?” the next question most people ask is “why should I run a pen test?”

There are a couple of reasons why most people perform penetration testing:

  1. To identify specific vulnerabilities in their network’s cybersecurity architecture so they can be fixed—including any flaws in the incident response plan; and

  2. To increase awareness about cybersecurity issues amongst the organization’s upper management—which can encourage increased cybersecurity budget allocation for new defenses and security education, training, and awareness initiatives.

Both objectives contribute to improving a business’s overall cybersecurity, which is always beneficial.

However, it is important to remember that penetration testing is not a “one and done” solution. Over time, there may be changes to the assets on the network, the software on those assets, or even new attack methods that emerge which target previously-unknown vulnerabilities. To maintain strong vulnerability management, organizations need to periodically run new pen tests.

The frequency of penetration tests will vary from one organization to the next, though. How frequently should your own organization run a pen test? The answer depends on how large your organization is, how frequently you add new software or hardware to your network, and the specific cybersecurity regulations that govern your industry.

Penetration Testing Approaches

There are a few different approaches cybersecurity experts can take when performing a penetration test. The key difference usually comes down to how much knowledge the theoretical attacker is assumed to have.

Black Box Penetration Test

This test is conducted without any knowledge of the targeted network or the systems running on it. The tester doesn’t know anything about the internal code or software and lacks any access credentials or sensitive information. This form of testing is realistic because it forces the tester to think like a potential hacker when searching for vulnerabilities. While it may seem like the most accurate form of testing, black box tests are constrained by time limits. The tester usually has a limited period of time to evaluate a system and try to gain access, whereas a hacker does not have similar constraints and could identify weaknesses that are not immediately obvious.

Gray Box Penetration Test

In this form of penetration testing, the tester possesses some baseline knowledge about the system. This could be lower-level credentials, a network infrastructure map, or application logic flow charts. The test will still produce very realistic results because many cyberattackers won’t even attempt to launch an attack without some information about the target environment. Since this approach essentially skips over the “reconnaissance” step and gets straight to the actual pen test, it can be performed more quickly and focus specifically on systems that are already known to be high-risk.

White Box Penetration Test

The final approach to penetration testing is less a simulated cyberattack than a thorough examination of a system at the source code level. Testers are granted the highest level of access privilege, allowing them to assess the system thoroughly for logic vulnerabilities, misconfigurations, poorly written code, and deficient security measures. While very comprehensive (and especially effective for preventing insider threats), it may not recognize gaps that an attacker would be able to exploit from the outside using unconventional tactics. For this reason, it’s often helpful to perform a white box test in conjunction with black or gray box testing.

Types of Penetration Tests

There are several different types of penetration tests used to evaluate the overall security of a network. Here are a few of the most common forms of penetration testing:

  1. Social Engineering Test: These tests attempt to make an employee reveal secure information, such as a password or a piece of sensitive data. They can be conducted by phone or through online communication and help to identify human-related security vulnerabilities.
  2. Network Services Test: This common test identifies openings in a network to determine where hackers may be able to gain access into a system.
  3. Web Application Test: An automated test that determines whether or not web applications and software programs running in the network environment contain security vulnerabilities.
  4. Physical Penetration Test: A brute force test that seeks to gain access through every physical network device and access point within a facility. This form of test is usually required for military and government organizations.
  5. Wireless Security Test: This test identifies open or unauthorized hotspots and WiFi access points and attempts to gain network access through them.
  6. Remote Dial-Up Test: Modems represent a potential weak point in a network. This test searches for modems in a network environment and tries to log into them using brute force methods to gain system access.

Penetration Testing Tools

There are a variety of automated tools testers can use to identify vulnerabilities in a network. Penetration testing tools typically scan code to look for any errors, loopholes, or malicious scripts that could increase the potential of a security breach.

While any managed security services provider will typically have a preferred penetration testing tool that they use, there are a few key features that any testing tool should possess.

  • Easy to Use: This may seem obvious, but deploying overly complicated and hard to manage pen testing software makes it more likely that something won’t be configured correctly or some vulnerability will be missed due to oversight.
  • Automated Verification: A good pen testing program should be able to verify any potential vulnerabilities automatically.
  • Vulnerability Prioritization: Any vulnerabilities should be categorized and prioritized according to their severity so that testers will know which security gaps require immediate attention.
  • Reverification: Known exploits should be easy to locate after they’ve been identified to facilitate speedy remediation.
  • Detailed Reporting Features: Once the penetration test is complete, the software needs to be able to generate a detailed, customizable log report that provides information about identified vulnerabilities.

Enhance Your Penetration Testing with Compuquip!

As a dedicated managed security services provider for companies in Florida and the Caribbean, Compuquip Cybersecurity has extensive experience with both automated and manual penetration tests. We use the latest techniques to evaluate your network systems and locate potential security gaps that could endanger your data and mission-critical applications. 

To learn more about our vulnerability assessment and penetration testing services, contact our team today and tell us all about your organization’s unique cybersecurity needs.

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