Sparring Partners

If you want to check your systems for security vulnerabilities, you need the right tools and a massive helping of experience. Prospective pen testers can get some practice by breaking into prefabricated training VMs.

- By Tim Schürmann

When you buy a new food processor, it will take you three glances at the manual, two creamy pea soups, and maybe a piece of your finger before you can correctly assess the danger of the blender blades at speed 6. Pen testing is not much different:

Hacking tools are only efficient if you know what they were designed for, how to use them, and what limits they have. Before you launch a full-scale attack on your own web server via its open ports, you will want to first get to know the most important tools and attempt a couple of simpler break-ins. It’s actually great fun.

Requirements

The starting point and basis for pen testing is your current technical skill set. Experience as an administrator is extremely useful. To crack an NGINX web server, for example, you need to understand the internal workings of the software and at least be able to set up the instance you are running.

Ideally, you will also have already hardened various systems against attacks. In other words, you know which vectors could be promising for intrusion attempts. Attacks usually start on the network and end up on the command line at some point. When you get there, you need to know what you are doing. Many hacker tools are designed as command line-only programs. DIY shell and Python scripts can also automate your attack attempts. Phishing can play a role in pen testing as well (see the box entitled “Phishing for Newcomers”). It is a massive advantage to have basic network knowledge, familiarity with the command line, and scripting skills.

DIY Store Visit

The first step is to obtain a toolbox with a selection of frequently required security tools. You can find these tools in Linux distributions that are explicitly designed for pen testers (see Table 1). Kali Linux [1] is particularly popular, as are Parrot [2], BackBox [3], BlackArch [4], and the Network Security Toolkit (NST) [5].