Security Challenges

2 minute read

a.k.a. “How the sausage gets made”

Cyber security is being widely accepted by companies around the world as a mean for defending their precious data and try to find the best cyber security experts on the market. But HR often turns a blind eye on how security experts become good security experts: can you imagine a cop who’s not able to put himself in a thief’s shoes? Good security experts usually have a deep understanding on how an attack is carried out and they often have to try and attack their own systems to check for vulnerabilities. How does a security enthusiast become a security expert? More often than not, they resort to borderline legal means, choosing random targets to hone their skills (that’s mostly what happened in the 90s / early 2000s, since a widespread company security culture didn’t exists), but over the last years a plethora of CTF sites came to life, allowing security enthusiast to try and attack a system while staying in a safe and legal environment.

Online Challenges

Some sites offer online security challenges (usually for Web Security) where attacks are carried out in sandbox so that they don’t affect the host system.

  • HackThisSite Challenges are presented as missions, with some fun background that helps the user to stay motivated on the task, but they are usually not clean cut and you have to find out on your own which are the best tools to complete the mission.
  • RingZer0 TeamChallenges are split in categories (shellcoding, javascript, binary, etc.) and get gradually harder.
  • W3Challs Challenges are split in categories as in RingZer0Team. This particular Challenge site asks his user not to post any solution online (except for the “afterwards” forum, as they call it, only accessible to users who completed that specific challenge), but you get some help from the Help forum of each challenge (spoiler-free).
  • OverTheWire Wargames Each Wargame has his own theme (Natas is WebSec-based, Bandit is for unix shell commands, etc.) and each level of a wargame contains the password for the next level.

Offline Challenges

Instead of offering online challenges, developers often release source codes to be deployed on a local stack (usually LAMP). Be careful!

  • Mutillidae 2 Being an OWASP project, it mainly focuses on the “OWASP Top 10 Web Application Security Risks” guide; challenges are then split by Security Risk (e.g. A1 - Injection) Languages: PHP + MySQL
  • DVWA (Damn Vulnerable Web Application) Challenges are split by type (Brute Force, Command Execution, etc.) and can be tweaked to be harder or easier by selecting an appropriate Security Level parameter (can be low, medium or high). Source code can be found hereLanguages: PHP + MySQL

Virtual Machines

Prebuilt virtual machines to be deployed on a local hypervisor (usually VirtualBox or VMware)

  • Metasploitable2 An Ubuntu based VM designed to be vulnerable and exploitable using the Metasploit framework.
  • VulnHub A website containing multiple vulnerable-by-design VMs. Environments are usually challenge specific, a mission is stated in the download page and the user has to try and carry it out on the downloaded VM.
  • Exploit Exercises There’s a smaller number of VMs, each with its own theme and challenges (Nebula is for simple to intermediate privilege escalation, Protostar and Fusion are for memory exploits), but in each VM you can find different levels, much like in Wargames.
  • WebSec Tutorial Also known as “shameless self-advertising”, this is my homemade Web Security gym. (Suggestions and contributions are welcomed