How to Do Penetration Testing & The Benefits of Outsourcing

Whether you’re a service-based business, B2B, government-affiliated, or non-profit organization, having a digital presence is absolutely essential in today’s market. The upside of this is that integrated advanced technologies such as cloud computing, IoT devices, and AI-driven systems enable companies to streamline operations, improve communication, and accelerate decision-making processes. The flip side, however, is the expanded attack surface that accompanies a robust digital infrastructure. In fact, organizations today have a greater number of vulnerabilities inherent in their digital networks than at any other time in history. Misconfigurations, outdated software/unpatched systems, access control, weak user credentials, and social engineering attacks are only a few examples. So what can organizations and their cybersecurity specialists do to mitigate these vulnerabilities? One answer is penetration testing. 

It’s important to note that there is no single method for detecting and accounting for all vulnerabilities. However, penetration testing is an invaluable method that should be a part of every organization’s cybersecurity strategy. It’s especially effective when handled by an MSSP who knows how to do penetration testing for maximum results.  

Shore up your cybersecurity — With custom-tailored services built to meet the needs of your organization, we help ensure operational continuity and data protection. Reach out today for a consultation. 

What is Penetration Testing? 

Penetration testing, or pen testing, is a method that involves simulating cyberattacks on a system, network, or application to identify vulnerabilities that could be exploited by attackers.  

Penetration testing is not a catch-all; but, it is highly effective in identifying a wide range of vulnerabilities, including: 

• Weak or compromised user credentials 

• Misconfigurations 

• OS and endpoint app vulnerabilities 

• Outdated software 

• Injection flaws (e.g. SQL) 

• Cross-site scripting 

If left unaddressed, these vulnerabilities can lead to unauthorized access, data exposure, system compromise, and other dangerous consequences. Penetration testing proactively flags these vulnerabilities so they can be addressed by cybersecurity professionals before bad actors can take advantage. 

How to Do Penetration Testing: An Inside Perspective 

When it comes to how to do penetration testing, there are a few different options available: 

• Open-box — Also known as white-box testing, this type requires the tester to have full knowledge of the system, including network maps, source code, and more. This type is best for simulating an insider attack or a well-informed external threat. 

• Closed-box — Also known as black-box testing, this is the opposite of open-box. The tester has no prior knowledge of the system and must rely on their own skills to discover vulnerabilities. This best simulates an attack from an outside bad actor. 

• Covert — Also called double-blind testing, a covert penetration test occurs when only a few people within the organization have prior knowledge of it. It’s useful for analyzing how well your cybersecurity team responds to a real attack without warning. 

• External — This type of penetration test focuses on externally facing systems, such as web applications, network servers, or other infrastructure exposed to the internet. It’s another method that is best for simulating an attack from outside the organization. 

• Internal — This test is conducted within the organization's network and simulates an attack by someone with insider access, such as an employee or someone who has breached the internal network. 

How to Do A Penetration Test: The Process 

Whatever kind of penetration test you’re running, it begins when your cybersecurity professionals (such as your MSSP) take on the role of “ethical hackers”. From there, if you want to know how to do a penetration test, you can expect a process that looks something like this: 

Step 1: Reconnaissance 

Reconnaissance, or recon, is where the penetration tester gathers as much information as possible about the target system. This may involve passive techniques, such as open-source intelligence (OSINT), where the tester collects data without directly interacting with the target. Or the tester may opt for active methods, such as network scanning, which involves probing the system for open ports, services, and other accessible information.  

In most cases, an experienced cybersecurity professional will use both active and passive methods. The goal is to build a comprehensive understanding of the system's architecture, potential entry points, and any exposed services that could be vulnerable to attack. 

Step 2: Identifying Vulnerabilities 

In this phase, the penetration tester analyzes the information gathered during reconnaissance to identify potential security weaknesses. This involves using automated tools, such as vulnerability scanners, as well as manual techniques to discover misconfigurations, outdated software, weak passwords, and other security flaws that could be exploited.  

The tester then maps these vulnerabilities to specific areas within the system that may be susceptible to attack, setting the stage for the next step. 

Step 3: Exploitation 

With vulnerabilities identified, it’s time for the next step: exploitation. This is the crux of how to do a penetration test. The cybersecurity professional attempts to exploit the vulnerabilities with the goal of analyzing the extent to which they could be leveraged by bad actors.  

This phase is conducted with care to preserve the system’s integrity and a number of specialized tools are typically implemented. If it falls within the scope of the test, the cybersecurity professional may even attempt lateral movement if the initial exploitation is successful. 

Step 4: Reporting 

Finally, once the test is concluded, the cybersecurity professional documents the findings in a detailed report. This report usually includes a summary of the test objectives, methods used,  vulnerabilities discovered, and the success or failure of exploitation attempts. 

The report also provides actionable recommendations for mitigating identified risks, prioritized based on their severity and impact. This step is crucial as it translates the technical results of the test into clear, understandable information that organization leaders can use to enhance their security posture. 

Why Outsource Penetration Testing to an MSSP? 

If you’re wondering how to do penetration testing for your own organization, consider outsourcing it to an MSSP. As specialists in cybersecurity, MSSPs bring a wealth of experience and resources to the table, all of which you’ll have full access to without the need to maintain a full-time, in-house security team. This ensures that the penetration testing is conducted with a high level of proficiency, leveraging the most current methodologies. 

It’s also sometimes important that penetration testing be conducted as objectively as possible, such as in the case of closed-box tests. Because an MSSP has no prior knowledge of the internal workings of the organization, they can approach the penetration test from the perspective of an external attacker. This objectivity is critical in identifying vulnerabilities that internal teams might overlook due to familiarity or assumptions about the security posture. 

And, perhaps most important, an MSSP allows you and your employees to focus on core business functions, leaving cybersecurity to the professionals. 

Stay Ahead of Cyber Attacks with Penetration Testing from Inversion6 

At Inversion6, we offer managed cybersecurity services specifically designed to address the unique challenges of your organization. Our solutions encompass everything from attack surface analysis and continuous 24/7 monitoring to managed SIEM and autonomous penetration testing, ensuring your digital infrastructure remains secure and resilient. With decades of experience, our team is composed of top-tier experts who bring deep industry knowledge to every aspect of your cybersecurity strategy. 

Don’t let a cyber attack expose the weak points in your digital defenses. Join forces with Inversion6 to fortify your cybersecurity and protect your most valuable assets. Reach out to us today to schedule a consultation.