How To Break Into Information Security

I’ve been asked a few times recently, usually by operations folk, to give some advice about how to break into the security sector, so under much pain I decided to commit my thoughts on the subject to this web log post. I’ve commented on this subject before and more extensively in chapter 6 of Security De-engineering, but this version is more in line with the times (up to 2012 I was advising a wide pass-by trajectory of planet infosec) and it will be shorter – you have my word(s).

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First I’d just be wary about trying to get into security just because of financial reasons (David Froud has an excellent blog and one of his posts covered this point well). At the time of writing it is possible to get into the field just by having an IT background and a CISSP. But don’t do that unless you have what’s REALLY required (do not judge what is REALLY required for the field based on job descriptions – at the time of writing, there are still plenty of mistakes being made by organisations). Summarising this in a very brief way:

  • You feel like you have grown out of pure IT-based roles and sort of excelled in whatever IT field you were involved in. You’re the IT professional who doesn’t just clear their problem tickets and switch off. You are, for example, looking for ways to automate things, and self-teach around the subject.
  • Don’t think about getting into security straight from higher education. Whereas it is possible, don’t do it. Just…don’t. Operational Security (or opsec/devopssec) is an option but have some awareness of what this is (scroll down to the end for an explanation).
  • Flexibility: can jump freely from a Cisco switch to an Oracle Database on any Operating System. Taking an example: some IT folk are religious about Unix and experience a mental block when it comes to Windows – this doesn’t work for security. Others have some kind of aversion to Cloud, whereas a better mindset for the field is one that embraces the challenge. Security pros in the “engineer” box should be enthusiastic about the new opportunities for learning offered by extended use of YAML, choosing the ideal federated identity management solution, Puppet, Azure Powershell, and so on. [In theory] projects where on-premise applications are being migrated to Cloud are not [in theory] such a bad place to be in security [in theory].
  • You like coding. Maybe you did some Python or some other scripting. What i’ve noticed is that coding skills are more frequently being seen as requirements. In fact I heard that one organisation went as far as putting candidates through a programming test for a security role. Python, Ruby, Shell ([Li,U]nix) and Powershell are common requirements these days. But even if role descriptions don’t mention coding as a requirement – having these skills demonstrates the kind of flexibility and enthusiasm that go well with infosec. “Regex” comes up a lot but if you’ve done lots of Python/Ruby and/or Unix sed/awk you will be more than familiar with regular expressions.

There is a non-tech element to security (sometimes referred to as “GRC”) but this is something you can get into later. Being aware of international standards and checking to see what’s in a typical corporate security policy is a good idea, but don’t be under the impression that you need to be able to recite verses from these. Generally speaking “writing stuff” and communication is more of a requirement in security than other fields, but you don’t need to be polished at day zero. There are some who see the progression path as Security Analyst –> Security Consultant (Analyst who can communicate effectively).

Another common motivator is hacker conferences or Mr Robot. Infosec isn’t like that. Even the dark side – you see Elliott with a hoody writing code with electronic techno-beats in the background, but hackers don’t write code to compromise networks to any huge degree, if at all. All the code is written for them by others mostly. And as with the femtocell and Raspberry Pi incidents, they usually have to assume a physical presence on the inside, or they are an internal employee themselves, or they dupe someone on the inside of the organisation under attack. Even if you’re in a testing role on the light side, the tests are vastly restricted and there’s a very canned approach to the whole thing with performance KPIs based on reports or something else that doesn’t link to actual intellectual value. Its far from glamorous. There’s an awful lot of misunderstanding out there. What is spoken about at hacker confz is interesting but its not usually stuff that is required to prove the existence of vulnerability in a commercial penetration test – most networks are not particularly well defended, and very little attention is given to results, more so because in most cases the only concern is getting ticks in boxes for an audit – and the auditors are often 12 years old and have never seen a command shell. Quality is rarely a concern.

Its a good practice to build up a list of the more influential bloggers and build up a decent Twitter feed and check what’s happening daily, but also, here are the books that I found most useful in terms of starting out in the field:

  • TCP/IP Illustrated – there are 3 volumes. 1 and 2 are the most useful. Then…
  • Building Internet Firewalls – really a very good way to understand some of the bigger picture ideas behind network architecture design and data flows. I hear rolling of eyes from some sectors, but the same principles apply to Cloud and other “modern” ideas that are from the 90s. With Cloud you have less control over network aspects but network access control and trust relationships are still very much a concern.
  • Network Security Assessment – the earlier versions are also still pertinent unless you will never see a Secure Shell or SMB port (hint: you will).
  • Security Engineering – there’s a very good chapter on Cryptography and Key Management.
  • The Art of Software Security Assessment – whether or not you will be doing appsec for a living you should look at OWASP‘s site and check out Webgoat. They are reportedly looking to bolster their API security coverage, which is nice (a lot of APIs are full of the same holes that were plugged in public apps by the same orgs some years ago). But if you are planning on network penetration testing or application security as a day job, then read this book, its priceless and still very applicable today.
  • The Phoenix Project – a good background illustrative for gaining a better understanding of the landscape in devops.

Also – take a look at perhaps a Windows security standard from the range of CIS benchmarks.

Finally – as i alluded earlier – opsec is not security. Why do i say this? Because i did come across many who believe they made it as a security pro once they joined a SOC/NOC team and then switched off. Security is a holistic function that covers the entire organisation – not just its IT estate, but its people, management, availability and resilience concerns, and processes. As an example – you could be part of a SOC team analysing the alerts generated by a SIEM (BTW some of the best SIEM material online is that written by Dr Anton Chuvakin). This is a very product centric role. So what knowledge is required to architect a SIEM and design its correlation rules? This is security. The same applies to IDS. Responding to alerts and working with the product is opsec. Security is designing the rulebase on an internal node that feeds off a strategically placed network tap. You need to know how hackers work among other areas (see above). Security is a holistic function. A further example: opsec takes the alerts generated by vulnerability management enterprise suites and maybe does some base false positives testing. But how does the organisation respond effectively to a discovered vulnerability? This is security.

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