Windows Pen Testing:
10 Powerful Tools and How to Perform It

Windows has long been the preferred platform for people all around the globe. The majority of offices rely on windows platforms to get their job done. As a result, when it comes to pen testing windows systems, there is a greater need for skilled individuals who can effectively find and mitigate vulnerabilities in these systems. This article will guide you through pen testing windows systems and will introduce you to the ten most powerful tools for the task.

What Is Pen Testing?

Pentesting, also known as ethical hacking, is the process of identifying vulnerabilities in a system and exploiting them to assess the security of that system. It can be used to check the strength of networks, systems, and applications against attacks.

Can You Do Pen Testing On Windows?

Yes! pen testing can be performed on any platform, including Windows. In fact, Windows is one of the most commonly targeted by cybercriminals and hence pen testing it is essential.

Additionally, it also includes assessing the security posture of Windows systems and the damage that could be caused by an attack on these systems.

Why Should You Know About Windows Pen Testing?

Knowing how to perform windows pen testing is important because most businesses rely on Windows-based systems. As a result, these systems are often targeted by hackers. By knowing how to pen test windows systems, you’ll be in a better position to defend against attacks.

10 powerful tools for windows pen testing

1. Astra Pentest:
Astra Security’s Astra Pentest is comprehensively one of the best penetration testing tools. It does an excellent job testing applications against 3000+ known vulnerabilities. It also gives you tips to fix them and determines the risk score. Additionally, Astra Security provides 24/7 support and can work remotely, so you can always get the help you need instantly.

2. OWASP ZAP:
This is an automated web application security scanner with a simple user interface. It is also free and open-source. OWASP ZAP can identify a variety of web application vulnerabilities including Cross-Site Scripting (XSS), Broken Authentication and Session Management, Injection Flaws, and more.

3. Nmap:
Nmap is a port scanner that can be used for windows pen testing. It is a free tool and comes included in Kali Linux. You can use Nmap to detect open ports.

4. Metasploit Framework:
The Metasploit Framework is usually the go-to pen testing tool for beginners. It is free to use and also comes included with Kali Linux. It allows you to exploit vulnerabilities and also write your own exploits.

5. Burp Suite Pro:
This is a commercial tool for web application pentesting. It includes many features such as an intercepting proxy, spider, scanner, and more. Burp Suite Pro is also available as a free trial.

6. Wireshark:
Wireshark is a network analyzer that can be used for windows pen testing. It allows you to capture and inspect packets, and also includes filters and features to help you analyse the data.

Wireshark is available as a free download.

7. SQLmap:
SQLmap is a tool for detecting and exploiting SQL injection vulnerabilities. It can be used for Windows pen testing as well as other platforms.

SQLmap is free to use and is also included in Kali Linux.

8. John the Ripper:
John the Ripper is a password cracking tool that can be used for cracking Windows passwords. It is free and also comes included in Kali Linux.

9. Hydra:
Hydra is another password cracking tool that can be used for Windows passwords as well as cracking network login passwords. It is another free tool and you can find it included in Kali Linux.

10. Nessus:
Nessus is a vulnerability scanner that can be used for windows pen testing. It is a paid tool, but there is also a free edition that you can use. Nessus can scan for a variety of vulnerabilities including weak passwords, open ports, and more.

How To Perform Windows Pen Testing?

Now that you know a little bit about the different tools that can be used for windows pen testing, let’s look at how to actually perform a penetration test.

First, get a clear idea about the target system. You can do this by scanning for open ports using Nmap or another port scanner.

Once you have identified the target system, you can start performing tests against it. Escalation of privileges is perhaps one of the most crucial aspects of Windows pen testing. To perform some tests, you will need elevated privileges. There are many ways to escalate privileges, including using Metasploit Framework or PowerShell scripting.

Once you have gained access to the system, you can start assessing the security posture and looking for vulnerabilities. The goal is to find as many vulnerabilities as possible and exploit them until you have control over the target system.

Conclusion

Windows pen testing can be a very powerful tool for assessing the security of your systems. By using the tools listed above, you can identify a variety of vulnerabilities and exploit them until you have control over the target system. Remember to always use caution when performing pen tests, as it is possible to damage or destroy data if you are not careful. Always test on a copy of the target system first to ensure that you do not cause any damage.

Ankit Pahuja is the Marketing Lead & Evangelist at Astra Security.
You can contact Ankit on Linkedin: linkedin.com/in/ankit-pahuja/