Updated March 1, 2025
Keeping your data and network safe and secure is a priority for any business. However, it’s a complex initiative that includes preparation for the many ways hackers can exploit vulnerabilities. As a result, organizations need various tools and practices to be as cyber-secure as possible. One of the best ways to understand risk and weaknesses is to conduct penetration testing.
In this article, we’ll discuss what penetration testing is, how it works, its benefits, and more.
What Is Penetration Testing?
A penetration test involves a simulated cyberattack to identify vulnerabilities in your network that would enable cybercriminals a way inside. Such an exercise can include attempted breaches for all types of application systems.
Penetration testers use the same techniques, tools, and strategies as attackers so that attacks mimic real-world situations. They are an effective way to determine if your network can withstand various attacks, both authenticated and unauthenticated.
How Does Penetration Testing Work?
Penetration testing has many aspects and considerations. We’ll cover access levels, testing methods, what you can test, and the phases of the exercise.
Access Levels
The first consideration in setting up penetration testing is how much information the penetration testers will have. There are three main levels of this:
- Black Box Penetration Testing, also known as Opaque Box: Teams have no prior knowledge of the target system’s internal structure. They play the role of a hacker, looking for any weakness to exploit.
- Gray Box Penetration Testing, also known as Semi-Opaque Box: In this option, testers have some context of the target system, including data structure, code, or algorithms, and may receive credentials. The strategy to penetrate is different, with users possibly developing test cases related to an architectural diagram of the system.
- White Box Penetration Testing, also known as Transparent Box: The final level provides pen testers access to systems and artifacts like source code and containers. They may also be able to enter servers running the system.
These levels coincide with penetration testing methods, which we’ll review next.
Penetration Testing Methods
You can experiment with different testing methods to understand many aspects of cybersecurity. Depending on what you want to test and what matters to you relating to data security, you can request any of these types of testing from a cybersecurity services firm.
- External testing: In this approach, the testers target visible assets of a company (e.g., web applications, company website, email, and domain name servers) to achieve access and extract data.
- Internal testing: This test happens behind the firewall to simulate what could happen after a human error, such as credentials stolen through phishing.
- Blind testing: A blind test only provides the tester with the company’s name. It gives security professionals a real-time view of how an application assault could happen.
- Double-blind testing: A double-blind test means the internal security teams do not know it’s happening. In such a scenario, staff would have to respond immediately to the threat.
- Targeted testing: Testers and technical folks work together in this option. It’s great training for your team and enables them to get feedback from a hacker perspective.
So, what can you test?
Types of Pen Tests
You can request to test everything, but you may not get the granularity that you need to understand vulnerabilities. Each type of penetration test focuses on different areas of IT infrastructure.
- Web applications: Tests the overall security and possible risks, such as code errors, broken authentication, and injections.
- Network security: Uncovers the exploitable issues on different networks that are associated with routers, switches, or network hosts. The test often uses weak assets or misconfigured assets to breach.
- Cloud security: Validates that the cloud deployment security is accurate and outlines overall risk and the likelihood that the infiltration could occur in cloud properties. It’s possible to do these for public, private, and hybrid clouds.
- IoT security: Uses a layered methodology to analyze devices and their interactions. As IoT devices are often a favorite way for hackers to gain entry, these weaknesses are critical to correct.
- Social engineering: Leverages phishing mechanisms and emails to test a network’s defense, detection, and reaction capabilities. It also critiques security training and if employees are applying what they learned.
- Medical device security: Tests medical devices, such as implantables and surgical robots, for vulnerabilities.
Next, let’s look at the phases of a penetration test.
Penetration Testing Phases
Most exercises for penetration involve six steps. Here’s what to expect in each.
Reconnaissance and Planning
In step one, the penetration testing team will gather information about the target from public and private sources to build an attack strategy. They may proceed with internet searches, domain registration information, social engineering, network scanning that’s not intrusive, and other tactics.
Additionally, this phase defines the scope and goals of a test, such as what to attack and how to attack.
Scanning
Next, penetration testers will employ tools to target the system for weaknesses. They typically look for open services, application security problems, and open-source vulnerabilities. The objective is to understand how the system will respond as a result of attempts of intrusion. This often includes both static (code inspection) and dynamic (code in running state) analysis.
Gaining Access
In step three, the testers launch attacks to gain access. They’re deploying the tools and techniques to breach the designated scope. Some of the most common tactics are cross-site scripting, SQL injection, malware, social engineering, or backdoors.
The aim is to find a vulnerability and go after it to see if the penetration testers can steal data, intercept traffic, or other means that would compromise the security of the system.
Maintaining Access
After gaining access, the penetration testers will try to maintain it to see if they achieve a persistent presence. Accomplishing this enables the testers to see how deep they can penetrate the network. The time frame could be months, as many real-world attacks can involve a lot of time for a hacker to do damage.
Analysis and Remediation
At the end of the test, the penetration testing firm delivers the results. The report will provide you with information regarding:
- What vulnerabilities were they able to exploit, and how
- If they were able to obtain sensitive data and extract or manipulate it
- The period of time the tester was able to remain in the system without detection
From this information, you would then work with security stakeholders internally and externally to formulate a plan to address these issues.
Retesting
Keep in mind that after you do these things, you’ll want to continue using penetration testing to determine effectiveness. Thus, it should be an ongoing practice because of all the value it brings. You should consider testing and retesting when you:
- Add network infrastructure or applications
- Apply security patches
- Upgrade infrastructure or applications
- Modify end-user policies
- Establish new locations
The Value of Penetration Testing
Penetration testing does require an investment of budget and time. However, it can deliver valuable results that keep you breach-free and compliant. You’ll be able to determine what security risks are most glaring. Since you have information regarding actual security threats, your organization can be more proactive about cybersecurity. Focusing on prevention is just as important as responding.
A penetration test also delivers insights into how your existing security protocols are working. It’s a new level of visibility into your digital environment. It’s an unbiased view of your security posture.
What Are the Benefits of Penetration Testing?
Even security-focused organizations that perform due diligence on how they build their tech stack and cloud properties have risks. The only way to eliminate them is to go offline, and that’s not an option in the modern world.
Instead, companies must be diligent about protecting their digital assets, and penetration testing offers insight into blind spots.
When you engage ethical security hackers to test your system, you can realize many more benefits, including:
- Identifying weaknesses that you may have previously been unaware of throughout your network
- Evaluating the robustness of your controls in place to divert attacks
- Ensuring compliance mandates relating to data privacy and security requirements, such as FDA, PCI DSS, SOC 2, HIPAA, and GDPR
- Finding “holes” in security assurance practices upstream (e.g., automated tools, configurations, coding standards, etc.)
- Locating unknown software flaws, even those that aren’t high-risk
- Determining qualitative and quantitative examples of current security posture to define areas that need more attention and likely more budget dollars
With the value and benefits that penetration testing offers companies, your next consideration is choosing a firm.
How to Select a Penetration Testing Provider
Penetration testing is a service that many cybersecurity businesses can conduct. There is a certain standardization of it, as demonstrated by the methods, types, and phases discussed above.
Ideally, you want to hire a firm with significant experience in the field. You want to look for technical prowess and ensure the company is excellent at communicating and collaborating. You need someone to guide you and keep you in the loop, as these projects can be complicated and last for months. Finally, find a partner to help you remedy what you discovered in the test so that you can fortify your security posture.
If you’d like to learn more about how we carry out penetration testing and our experience, contact us today.
