So, you want to become a penetration tester, where do you start?

Introductions

Really the place to start is Robin Wood's two "Breaking in to Security" blog posts, which are here and here.

After that watch this great twenty minute interview with John Carroll on what it's like to be a penetration tester.

Now you have some context, work through "Start In InfoSec", put up by Rob Fuller, also known as Mubix. His Twitter feed is here: https://twitter.com/mubix. There's a considerable number of resources there, don't be afraid to pick and choose, move on to the next entry if the subject matter or the tone isn't relevant.

There's also a lot of information listed in "Getting Started in Information Security" on the netsec sub-reddit wiki here: https://www.reddit.com/r/netsec/wiki/start. While not directly useful this is handy to see the breadth of the subject matter, and what resources are available. Overall "/r/netsec" is worth your time as long as you aggressively filter. The regular hiring threads, while mainly focused on North America, are also worth following.

Attack Platforms

Kali is definitely the attack platform that many penetration testers use, and the most common. However it's also worth looking at BlackArch .

I would recommend running these as a virtual machine, however if you're looking at attacks at Layer 2, such as VLAN Hopping, you may have issues and ideally you'll run your attack platform directly from your laptop.

There are other platforms available, and also you may prefer to "roll your own" rather than having the platform maintainer decide how you work and what interface you use.

Offensive Tools

Depending on where you'll focus as a penetration tester you'll either need to become very familiar with very few tools, or at least have an understanding of a wide range of tools. These are good ones to start off with:

  • Nmap - the industry default for port scanning.
  • Nessus - this tends to be the vulnerability scanner that companies will use, and expect you to know.
  • Metasploit - a well maintained collection of attacks and an industry default.
  • Nikto - useful to see just how simple some tools can be, and the strengths and weaknesses of that approach.
  • SqlMap - SQL injection is still a major weakness on websites, this program automates exploiting it.
  • Burp Suite - the free version is enough for you to get the hang of this software, which is an industry default for web application testing.
  • Kismet - for analysis wireless networks.
  • Aircrack-NG - for testing wireless networks.

Targets To Attack

Of course you should only be attacking systems that you control, and have authorisation to do so. I always think it's much better to attack something locally that you're running as a virtual machine rather than to attack a Virtual Private System ( VPS ) you've paid for on the Internet. The best resource I've found is Awesome Cyber Skills as a list of systems to download, or access online.

Other Notes

As per my presentation, if you're interested in physical Social Engineering look at films such as Sneakers or the TV series Leverage just for flavour, look at the YouTube videos of Jayson Street and Johnny Long to see how professionals do it. Also check out the "career" of Karl Power and the book "The Complete Guide To Gatecrashing" to obtain interesting and entertaining insights into what's possible, and the mental challenges involved.

I expect similar examples of real world security failures to be present in Channel Four's "Britain's Greatest Hoaxer" documentary, which is on this week.

For real world examples of where this is important, look at the "KVM Hack" of Santander, and much more recently, the taping of members of the Republican Party...