Are you looking to become a Professional Penetration Tester? Here are the Top 5 Things You need to know before becoming a Professional Penetration Tester: Number 5 is the most important.
College Doesn’t matter:
Over the years I have worked with a lot of people. And in that time, I have found that Traditional College degrees do not matter. Some of the smartest and most talented people I have had the pleasure of working with were merely High School Graduates. They never spent a single day in a Traditional College. On the flip side, some College Graduates I have worked with that had their computer science degrees were very book smart, but when it came to putting those book smarts to their hands to action their skills, they were clueless.
Certifications do Matter:
While Traditional College degrees are falling by the wayside, even less required by employers, industry certifications however, are taking place of that. Let’s be honest, I think even that is going to be phased out in the next decade. Why? Just take a look around, there are a myriad of Professional Certifications these days. CEH, LPT, CISSP, OSCP, Sec+, to just name a few. And for the most part, they all test basically the same skills. And here’s the thing about these Certifications. Most of them have a re-test period, in which that Certification you worked so hard for expires in a period of time. Now, don’t get me wrong, this industry of Penetration Testing and Information Security does change rapidly, so it’s not really a bad thing to re-test. But think of the amount of money and time you have to devote to a re-cert every 2 or so years. It ads up quickly.
This is a MUST in my experience. Most of the tools we use in every day Penetration Testing tasks simply do not exist in the Windows Space, and only about half of them exist in the Apple/Mac space. There are many reasons for this. The most important reason is because Linux is open source, and the networking stack is very much more robust than its windows counterpart. So, while you do not need to be a Master Linux Super Guru, you do need to understand the basics of how it works, and some simple commands before you can pentest from a Linux Environment.
This is another must. You must know the basics of how a Network and it’s basic protocols work in order to be successful at Penetration Testing. Now again, you don’t need to be a network engineer here, but you should have a basic understanding of TCP/IP, Packet Structure, and other protocols such as HTTP, UDP, ICMP, OSI Model, just to name a few. The more you know in this area, the better and faster you will be.
The weakest link in any security environment is the human element. And that is a fact. Now you don’t need to be a psychology major here, but you should understand how people tend to think.
For instance, lets say that you Pentester a Company called XYZ Widgets International, and you simply can not find a way in. They are super secure. So, in your Information Gathering phase, you find a company directory, full with names, numbers, and most importantly email addresses. You have also managed to stumble upon a portion of their website, where you can see their “Partners” i.e. other companies they deal with. You pick the partner ABC Widget Wholesalers, Inc, who has a manager of partnerships named Michael Dawson.
So, in the company directory of XYZ Widgets you find Mary Adams. She’s a secretary for the office. You also found in that list a higher level employee, such as a manager of partner relations named James Matthews.
So you craft yourself a pdf with a reverse_tcp meterpreter shell, pack it with your packer of choice, and craft a spoofed email from firstname.lastname@example.org. In this email, you put a subject line of: “URGENT – Partner Application”. In the body of the email you put something like “Mary, I need your help. My boss Michael Dawson is having issues with his email or something. Ugh, you know how that is. He’s screaming at me about it, like I know anything about computers! Anyway, I am trying to help him, so he asked me to email this Partner Application to you. Could you please download it and print it out. It needs to be signed by James Matthews, and returned by email to me by no later than 2pm today. Thanks! – Sam Smith – Assistant to Michael Dawson”
Lets talk about this for a minute.
Mary Adams, being just a secretary probably doesn’t know much about computers, and to be honest, she’s probably on some shoe shopping site, browsing for a new set of heels or something. Bing, email pops up. She quickly glances at the subject line and see’s “URGENT – Partner Application”, looks at the sender, and it comes from abcwholesaler.com – one of their partners. Mary doesn’t want to get in trouble, so she quickly opens the email, see’s her first name which builds validation of legitimacy. Then she sees her name again, this time followed by “I need your help” — she’s a secretary, she’s always doing something for bosses. This set’s her mind back into work mode, and away from shoe shopping mode. You mention your boss, so that immediately lets her know that you are a lower level person in the company, just like her. You then follow by saying that your boss is having email problems (tells her why you are emailing her instead of Mr. Dawson), and throw in the UGH at the end. This gets her mind into a place of compassion, because likely she’s been there too. You heighten the sense of urgency saying “He’s screaming at me about him email problems”, builds on the URGENCY clause you had in the subject line, and followed up with “Like I know something about computers”, which builds trust again that you are a low level employee just like her, and how bosses can be unreasonable. Now, you give her the Call To Action with sincerity – “Can you please download this, and print it out?” The Call To Action tells her brain that she needs to do this. You then follow with “It needs to be signed by James Matthews” – probably one of her many bosses. This one sentence alone does 3 things here: Again another sense of Urgency by mentioning her bosses name, Persuades her not to be lazy and forward it, since it needs to be printed, to be signed. You give her a dealine, sealing the urgency deal.
You should now have a shell on Mary’s machine. Social Engineering is one of the most important things to know in becoming a Penetration Tester.