10 Skills Needed to be a Successful Pentester

  1. Mastery of an operating system. I can’t stress how important it is. So many people want to become hackers or systems security experts, without actually knowing the systems they’re supposed to be hacking or securing. It’s common knowledge that once you’re on a target/victim, you need to somewhat put on the hat of a sysadmin. After all, having root means nothing if you don’t know what to do with root. How can you cover your tracks if you don’t even know where you’ve left tracks? If you don’t know the OS in detail, how can you possibly know everywhere things are logged?
  2. Good knowledge of networking and network protocols. Being able to list the OSI model DOES NOT qualify as knowing networking and network protocols. You must know TCP in and out. Not just that it stands for Transmission Control Protocol, but actually know that structure of the packet, know what’s in it, know how it works in detail. A good place to start is TCP/IP Illustrated by W. Richard Stevens (either edition works). Know the difference between TCP and UDP. Understand routing, be able to in detail describe how a packet gets from one place to another. Know how DNS works, and know it in detail. Understand ARP, how it’s used, why it’s used. Understand DHCP. What’s the process for getting an automatic IP address? What happens when you plug in? What type of traffic does your NIC generate when it’s plugged in and tries to get an automatically assigned address? Is it layer 2 traffic? Layer 3 traffic?
  3. If you don’t understand the things in item 2, then you can’t possibly understand how an ARP Spoof or a MiTM attack actually works. In short how can you violate or manipulate a process, if you don’t even know how the process works, or worse, you don’t even know the process exists! Which brings me to the next point. In general you should be curious as to how things work. I’ve evaluated some awesome products in the last 10 years, and honestly, after I see it work, the first thing that comes to my mind is “how does it work”.
  4. Learn some basic scripting. Start with something simple like vbs or Bash. As a matter of fact, I’ll be posting a “Using Bash Scripts to Automate Recon” video tonight. So if you don’t have anywhere else to start, you can start there! Eventually you’ll want to graduate from scripting and start learning to actually code/program or in short write basic software (hello world DOES NOT count).
  5. Get yourself a basic firewall, and learn how to configure it to block/allow only what you want. Then practice defeating it. You can find cheap used routers and firewalls on ebay, or maybe ask your company for old ones. Start with simple ACL’s on a router. Learn how to scan past them using basic IP spoofing and other simple techniques. There’s not better way to understand these concepts than to apply them. Once you’re mastered this, you can move to a PIX, or ASA and start the process over again. Start experimenting with trying to push Unicode through it, and other attacks. Spend time on this site and other places to find info on doing these things. Really the point is to learn to do them.
  6. Know some forensics! This will only make you better at covering your tracks. The implications should be obvious.
  7. Eventually learn a programming language, then learn a few more. Don’t go and by a “How to program in C” book or anything like that. Figure out something you want to automate, or think of something simple you’d like to create. For example, a small port scanner. Grab a few other port scanners (like nmap), look at the source code, see if you can figure any of it out. Then ask questions on forums and other places. Trust me, it’ll start off REALLY shaky, but just keep chugging away!
  8. Have a desire and drive to learn new stuff. This is a must; It’s probably more important than everything else listed here. You need to be willing to put in some of your own time (time you’re not getting paid for), to really get a handle on things and stay up to date.
  9. Learn a little about databases, and how they work. Go download mysql, read some of the tutorials on how to create simple sample databases. I’m not saying you need to be a DB expert, but knowing the basic constructs help.
  10. Always be willing to interact and share your knowledge with like minded professionals and other smart people. Some of the most amazing hackers I know have jobs like pizza delivery, janitorial, one is a marketing exec, another is actually an MD. They do this strictly because they love to. And one thing I see in them all is their excitement and willingness to share what they’ve learned with people who actually care to listen and are interested in the same.

Keatron Evans is a Senior Instructor for InfoSec Institute. InfoSec Institute is a security certification company that has trained over 15,000 people including popular CEH and CCNA certification courses.


  • anon

    This reads more like how to be a black hat rather then pentester.