Different Operating Systems for Different Tests
In general, penetration testers like to use Linux distributions for most of their work. The high levels of control and customization that are offered make it an easy choice. Linux also comes with the advantage of being open-source. Within Linux, there are many different distributions that come with different advantages. It is not necessary to use different ones for different tasks, but many people prefer the segmentation.
Some popular general-use operating systems are Kali, Parrot, and Black Arch. All of these provide the tools needed to start performing penetration tests out of the box. They are all preloaded with various tools, scripts, wordlists, and settings that greatly cut down on the time required to get started. Kali and Parrot are based on Debian. Debian is a very fast and powerful distribution. It is often thought of as slightly more complex than other distributions, such as Ubuntu, but can provide more granular control. Black Arch is based on Arch Linux, which is known for being extremely fast and lightweight. Arch will often require more work to set up properly and is a bit more minimal, but can work great for penetration testing once properly configured.
Penetration testing operating systems can also have more narrow use cases. Samurai is an operating system based on Ubuntu that is geared towards web application penetration testing. Samurai cuts out many of the tools that will not have much use for other types of tests and comprehensively covers anything that a tester could need during a web application assessment. Being based on Ubuntu, it is very user-friendly and simple to use, allowing beginners to easily introduce themselves to web application testing.
Digital investigators have some operating systems geared towards what they will need. These operating systems are largely focused on passive investigation and stealth as opposed to active exploitation. Some examples of these are Buscador and Trace Labs OSINT VM. Buscador is based on Ubuntu, while Trace Labs OSINT VM is based on Kali. These OSes come preloaded with all of the tools an investigator could need to perform passive reconnaissance on their target. Much of this is focused on open-source intelligence or OSINT gathering.
Usage of Windows for Penetration Testing
Windows machines can provide value to penetration testers in a few different ways. Typically, during tests, clients will have much of their infrastructure running on Windows. Knowledge of how this works can allow the tester to properly navigate their network. Especially during an internal penetration test, Windows machines have native capacity that can greatly assist testers. Many commonly used tools are available for Windows that can assist testers in gaining and elevating access within internal networks.
Many testers even choose to use Windows as their main operating system. This has the advantage of being very user-friendly and familiar to many people, as Linux can be a bit foreign to some. Common tools are increasingly being produced with Windows binaries that make this more and more possible. Windows coming with PowerShell natively installed is also a great bonus, as it is an extremely powerful scripting language.
Matching the Target Environment
There are many cases where it can be in the penetration tester’s best interest to simply emulate the OS of whatever they are testing. This has the advantage of allowing them to test certain potentially dangerous exploits in a safe environment. This can also be helpful when trying to develop custom exploits. Various dependencies and components can make it difficult to properly compile exploits on different machines. If the tester can closely recreate the client’s device, then it will be much easier to develop a working exploit.
Consult Our Team of Penetration Testers
Our penetration testers have developed a mastery of many different operating systems and tools to give us an edge when it comes to security. We can work with you to apply our expertise and provide your organization with lasting defense against cyber attacks. Contact us to learn more.
