Breaking into InfoSec: A Beginners Curriculum

While perusing /r/netsecstudents, it seems that every other day there is a thread asking for advice on how to break into the InfoSec world and where to start studying.
As helpful as the responses are, they tend to vary widely and are dependent on who can be bothered replying with the same answer each and every time.

As such, I thought I’d post up a rough guide for beginning your adventures should you be a newbie looking to move into information security (primarily pentesting, bounty hunting, and red teaming). This is by no means comprehensive and is simply based on my own experiences. It’s also incredibly video-heavy, so that’s something I guess.

Everything you do will be based on networking fundamentals and as much as it sucks, the old adage of “You have to walk before you can run” really does apply.

Feel free to jump around the list. If something is draining your soul, move on and come back. Seriously, until you get to the OSCP stage in this list it can be crushingly boring and if your mind starts to wander you will begin glazing over and miss something pretty important.

The greatest lesson you can take from dealing with the fundamentals is developing patience and learning to manage frustration. If you cannot learn to control apocalyptic levels of frustration, then it’s probably not advisable to read any further because this whole industry feeds on frustration; it’s basically a kink.

I am currently a Managing Security Consultant for a small spearhead team in a global corporation. We perform red teaming, phishing training, pentests, vuln scanning, breach assessments, and baseline security assessments. I come from a healthcare IT and applications background and teach people how to go fast on motorbikes on the side.

*Word of caution: Be aware that a large majority of people who move into this industry come with at least 5 years experience in other IT fields (often more) and without being a downer, you’ll probably never out-dance an ex dev; those dudes turn into raid bosses.
While there are plenty of young guns straight out of uni and some naturally talented freaks in their teens doing this, it is an industry that heavily benefits those with career and life experience. It requires a constant desire to learn and significant mental fortitude.

*Second word of caution: This writeup is beginning to age, and some sites may have since changed for better or worse. If you feel something seems out of place or dodgey then please leave a comment and I’ll look into replacing it.

Networking Fundamentals:

• CompTIA Network+ N10-007 Playlist
  • 101 videos taking you from an absolute beginner to competent in networking.
  • Set the videos to speed x1.25 or x1.5 to save yourself a lot of time and boredom.
  • Take notes to reference in the future (seriously, do it)
    *Updated to N10-007
• CompTIA A+ Playlist 1 – Playlist 2
  • 137 total videos
  • This is really aimed at less experienced people. If you’ve got any IT background, you can skip it.
    *Updated to 220-1001 and 220-1002

Active Directory
This should give you an understanding of how AD works.

• Introduction to AD infrastructure in Windows Server 2012
• Installing AD, DNS, and DHCP to Create a Windows Server 2012 Domain Controller
• Adding Windows Computers to a Windows Server 2012 Domain

Linux Essentials Playlist
An understanding of Linux, and comfort using it is a must. Install a VM or dual boot it; using it every day is the quickest way to learn. It’s pretty alien if all you’ve known is Windows, but boy is it beautifully efficient and simple once you understand it.
You can use the Linux Newbie Guide to quickly help you find or remember commands; bookmark it and then forget about it for years like I did.

Windows SysAdmin Essentials (suggested by LonerVamp)
This is a Lynda course which requires a membership, or you can try it for free. Well worth investing a months sub to go through it.
This course focuses on Server 2012, though it’d be worth browsing other material.
Server 2008 is a common find in the real world, and unfortunately, 2003 is all too common as well, so try become familiar with them all. Server environments are different beasts to everyday desktops.

Additionally, the Microsoft Video Courses ‘Windows Server Administration’ series is extremely well done, and you feel like you’re watching a sports show.

Security Fundamentals:

• CompTIA Security+ Playlists
  • Part 1 – 189 videos
  • Part 2 – 73 videos
• CISSP Playlist (For those completely new to security) *Updated to 2018 playlist. The old one was taken down. Be aware I have not watched this specific list.
• Computerphile Channel
  • Watch everything from Tom Scott and Dr Mike Pound. They give extremely user-friendly explanations of common security concepts.
  • Tom’s SQL Injection Explanation
  • Mike’s SQL Injection Practical Example

Courses:

At this stage, you would be more than comfortable beginning your OSCP (Offensive Security Certified Professional) adventures. If you’re not feeling it, jump down to VulnHub and HackTheBox to get a bit more ready for free.
The OSCP is one of (if not) the best certifications out there and is birth by fire approach. You will receive detailed course material and VPN access to a virtual lab filled with machines you can learn to hack.
Lab access is from 15 to 90 days, with the ability to extend as much as you want so long as you have the dosh.
At the end is a 24-hour exam.

The OSCP is run by Offensive Security and worth every penny.

In the event you cannot afford to sign up for the OSCP yet (or you just want more stuff) then see below for a DIY approach.

Oh, and download Kali Linux here. *Don’t run Kali as your daily OS, it’s not designed for that and makes you look like a skiddy.

Cybrary Courses
Cybrary is a wonderful platform filled with a plethora of courses for the aspiring <insert role>. It’s free, and you can get little certification pictures to put on your LinkedIn. Neat. They’re not overly weighty when it comes to resume’s but they do show a commitment to learning which is taken into consideration.
*I was recently informed that Cybrary is no longer a primarily free resource and now requires an upgraded account for many of the courses – including the original recommendations below.
I have had a quick squizz at what is available for free and linked them instead. Please be aware that I have not done these newer linked courses and as such, I cannot speak to their quality. If you give them a try, let me know what you think.

• Ethical Hacking and Penetration Testing with Kali Linux Certification Training Course
• Web Application Penetration Testing Course
• Introduction to IT & Cybersecurity Course
• Penetration Testing and Ethical Hacking Course

Pentester Academy offers detailed video courses for an affordable subscription fee.
If you have not done the OSCP course work then I’d recommend completing at a minimum:

• Pentesting with Metasploit Link
• Network Pentesting Link
• Web Application Pentesting Link
• Python for Pentesters Link
• Exploiting Simple Buffer Overflows on Win32 Link

Hacksplaining is a free to use site with expertly crafted mini-courses on all the fundamentals of web application hacking. You can chew through the whole site in an afternoon and it will greatly improve your understanding of website attack concepts.

PentesterLab is another site with short, self-contained lessons, both free and subscription-based. There are badges to complete which can also be displayed on your LinkedIn.

HackTheBox is a free to use virtual lab where you can practice your hacking skills. The only caveat is you have to hack your own invite code. There are videos and guides all over the net on how to do this, but I implore you, DON’T CHEAT. Get the code yourself, it’s not too hard and you will gain a tremendous amount of satisfaction from it. Also, if you can’t get the code, you sure as hell won’t get any of the boxes inside.

HTB is definitely one of my favourites on this list; they have a good-sized admin team with continuous development, a stream of new community-made vuln boxes to play with that rotate in, retired boxes available to VIP’s, and professional labs. The VIP memberships are well worth it as you get placed on a much smaller VLAN which avoids the hassle of other people hitting the same box as you.

Practical Pentest Labs is another virtual lab environment to practice hacking. I have not personally played in here yet, but I’ve heard good things so far.

Coding
A lot of people ask what is a good first language to learn, and without a doubt, one of the handiest to have in security is Python.
Practice Python takes you from a complete and utter novice to a hardcore Python programmer. Seriously, I suck at coding and always have. This site was the FIRST thing that has ever got me to understand programming language, and I can even write baby scripts to do things I’m too lazy to do now. I cannot recommend this site highly enough.

PHP is another must-have language as it is extremely common when dealing with web content.

VulnHub is a user-driven site filled with virtual machines to try and hack. You download them and host them yourself, then battle away. They range from easy to bananas. Check out beginner ones first and definitely look up Metasploitable.

OverTheWire is a site for war games where you move through levels designed to encourage skill growth and self-learning. This was suggested by a reader (Leithreas), and I have since gone and completed the ‘Bandit’ challenges, which were a tremendous amount of fun.
The learning process is very similar to ‘Practice Python’ and gives a lot of insight into messing around in Linux.
I did notice the difficulty has certain spikes and is not necessarily linear, but the knowledge gained is invaluable.

Books
If you enjoy reading or want to start building your collection, then a good start is anything from the list below. Obviously, there’s a tremendous (DT) amount of books to recommend, but I can’t remember them all so here’s a few. Be aware that the RTFM and BTFM won’t exactly “teach” anything, but are just excellent command reference books to have on hand.

• RTFM – Red Team Field Manual
• BTFM – Blue Team Field Manual
• Violent Python
• Nmap Network Scanning (only for those who chew through books like candy)
• The Hackers Playbook 2
• Basic Security Testing with Kali Linux 2
• Intermediate Security Testing with Kali Linux 2

Podcasts
To play on the train or in your car.

• Security Weekly Podcast
• Risky Business Podcast
• Secure Digital Life Podcast/Videos (Amusing as well as interesting)
• Daily Information Security Podcast (5-10 mins, easy short listening)

Continued Learning

• SecurityTube Site
  • It’s YouTube. For security. A never-ending pit of stuff to watch.
• The Big Blog Post of Information Security Training Materials
  • A recent collection of resources put together by u/667SlaysAyysForDays

Blogs

If you don’t already follow certain blogs, then you’ll soon realise just how valuable random people posting stuff can be. Often you can find answers to anything you need on a blog or a forum post.
As such, the following are some good starter pages to bookmark and reference as you go.

• g0tmi1k is a well-known figure in the industry, and has mountains of invaluable information and cheat sheets for beginners and advanced testers alike.
• Active Directory Security focuses on AD & Enterprise Security, securing methods, attack and defence tactics, along with a slew of notes and trivia.
• Security Sift Not updated for some time now, but still contains valuable information relating to breaches, exploits, and a multitude of other security-related topics.
• Lenny Zeltser has some great cheat sheets to which you can refer; with things such as a checklist on ‘How to Suck at Information Security‘, ‘Tips For Getting the Right IT Job‘, ‘Malware Analysis‘ etc..

I’ll make edits as I receive feedback and think of other things, so check back periodically.

Enjoy.

*Added Blogs
*Updated HackTheBox
*Updated Networking Fundamentals (N10-006)
*Added OverTheWire war games – Suggested by Leithreas
*Added ‘Linux Newbie Guide‘ under Linux Essentials, Lenny Zeltser cheat sheets, Secure Digital Life Podcast/Video, Daily Information Security Podcast (Suggested by PC509) – 11/05/18
*Updated CISSP playlist – 5/11/18
*Added ‘The Big Blog Post of Information Security Training Materials‘ – 6/11/18
*Updated Networking Fundamentals (N10-007) – 30/12/18
*Updated CompTIA A+ – 25/07/19
*Replaced Cybrary courses – 25/07/19
*Added a second word of caution – 25/07/19