Penetration Testing on Windows: 7 Essential Tools You Will Need

cyber attack

Are you worried about the security of sensitive data that is sitting in that Windows system right now? If yes, then rightfully so. Operating systems are in the end still computer codes put together. And just like any other computer code, Windows systems too have their flaws. Penetration testing your Windows system might be an eye-opening experience, and it just might be what you need to shore up your security posture.

But is penetration testing on Windows even possible? Let’s find out.

Windows Security Issues: The Elephant in the Room

There are numerous security concerns when it comes to Windows operating systems. Microsoft has long been known for its lax attitude towards security. This was one of the main reasons for the rise of Windows viruses in the early days of computing. Though they have upped their security game since then, hackers have been quick to adapt to them. A typical Windows system today is prone to:

  • Password cracking and reverse hashing
  • Network attacks
  • Powershell scripting attacks and privilege escalations
  • Exploit codes and malicious files
  • Human error

Your firewall and antivirus software could do half the job in protecting you against these risks but then again, there is only so much they can do. Most Windows systems don’t even ship with an antivirus solution that’s not just a free trial.

What is penetration testing and can you do it on Windows systems?

Penetration testing, or ethical hacking as some like to call it, is nothing but the process of hacking your own systems and networks to find security flaws. With that being said, Windows systems are hackable, and performing online penetration tests on them doesn’t void your warranty like it would for a macOS.

3 types of penetration testing

White-box pentesting: This is the most common type of pentesting, where the testers have full knowledge of the internal workings of the system.

Black-box pentesting: This is where the testers have no knowledge whatsoever about how the system works and they are given access only to what’s visible from the outside.

Grey-box pentesting: This is a mix of the two, where the testers have some knowledge about how the system works but not all of it.

Now that we know what penetration testing is, let’s take a look at how it works.

How does penetration testing work?

5 stages of penetration testing

The process of pentesting can be broadly divided into five stages:

  1. Reconnaissance: This is the first step where the tester attempts to collect as much data as possible about the targeted environment for testing. This might be accomplished through online research, social engineering, and footprinting.
  2. Scanning: In this stage, the tester scans the target system for vulnerabilities using various tools and techniques.
  3. Exploitation: This is where the tester tries to use a variety of hacks, tools, etc. to obtain unauthorised access to the systems.
  4. Maintaining Access: In this stage, the tester tries to maintain access to the system by installing backdoors and Trojans.
  5. Covering up tracks: This is where the tester cleans up any evidence of their activities on the target system.

Not all of the five stages need to be performed. If the tester is an insider and has direct access to the Windows system, stage one can be easily skipped. Stages four and five, are not entirely necessary since by this point you have found out some vulnerabilities and can move on to fixing them.

7 best penetration testing tools for windows

  1. Astra Pentest: This is a comprehensive pentesting tool that performs vulnerability assessments. Based on the initial scan it will then perform penetration tests against 3000+ known vulnerabilities. In the end, you get to view threats it protects you against, risk scores and severity of each vulnerability along with tips to fix them. Astra Security, the company behind this tool, is always available via chat support. You can also rely on their security experts should you need manual software penetration testing done.
  2. Metasploit: This is a popular framework for developing payloads (malicious code). It tailors the exploit code to work successfully against specific Windows versions if specified.
  3. Nmap: This is a powerful network scanning tool that can be used to scan for vulnerable ports and services on a target system.
  4. Wireshark: This is a network analysis tool that can be used to capture and inspect packets on a network.
  5. John the Ripper: This is a free tool widely used for cracking and revealing passwords. It works on all platforms and also comes pre-installed in Kali Linux.
  6. OpenVAS: This is a comprehensive vulnerability scanning tool that works for all operating systems including Windows systems. It also tells you how to fix each security flaw or direct you towards the Windows update that addressed said flaw.
  7. Kiwi (formerly Mimikatz): This is a tool for escalating privileges and gaining access to systems including Windows. You can also extract passwords and other sensitive data from Windows memory dumps.


Windows systems are not as secure as we would like them to be, but with proper pentesting, you can find and fix the vulnerabilities before they are exploited by attackers. The tools mentioned in this article will help you do just that. Go ahead and apply these measures to protect your networks. And keep in mind that security isn’t something you do once and then forget about; it’s a continuous commitment that requires constant attention.

So there you have it – penetration testing on Windows in a nutshell. As you can see, it’s a long, complicated procedure with several distinct phases and tools. But with the right knowledge and tools, you can secure your systems against even the most determined attackers.