3 Lessons From 30 Years of Penetration Testing

I’ve been doing penetration tests for 30 years and here are 3 things that have stuck with me.

I’ve been doing penetration testing for around 3 decades now. I started doing security testing back when the majority of the world was dial-up access to systems. I’ve worked on thousands of devices, systems, network and applications – from the most sensitive systems in the world to some of the dumbest and most inane mobile apps (you know who you are…) that still have in-game purchases. 

Over that time, these three lessons have stayed with me. They may not be the biggest lessons I’ve learned, or the most impactful, but they are the ones that have stuck with me in my career the longest. 

Lesson 1: The small things make or break a penetration test. The devil loves to hide in the details.

Often people love to hear about the huge security issues. They thrill or gasp at the times when you find that breathtaking hole that causes the whole thing to collapse. But, for me, the vulnerabilities that I’m most proud of, looking back across my career are the more nuanced ones. The ones where I noticed something small and seemingly deeply detailed. You know the issues like this, you talk about them to the developer and they respond with “So what?” and then you show them that small mistake opens a window that allows you to causally step inside to steal their most critical data…

Time and time again, I’ve seen nuance vulnerabilities hidden in encoded strings or hex values. Bad assumptions disguised in application session management or poorly engineered work flows. I’ve seen developers and engineers make mistakes that are so deeply hidden in the protocol exchanges or packet stream that anyone just running automated tools would have missed it. Those are my favorites. So, my penetration testing friend, pay attention to the deep details. Lots of devils hide there, and a few of those can often lead to the promised land. Do the hard work. Test every attack surface and threat vector, even if the other surfaces resisted, sometimes you can find a subtle, almost hidden attack surface that no one else noticed and make use of it.

Lesson 2: A penetration test is usually judged by the report. Master report writing to become a better penetration tester. 

This is one of the hardest things for my mentees to grasp. You can geek out with other testers and security nerds about your latest uber stack smash or the elegant way you optimized the memory space of your exploit – but customers won’t care. Save yourself the heartbreak and disappointment, and save them the glazed eyes look that comes about when you present it to them. They ONLY CARE about the report.

The report has to be well written. It has to be clear. It has to be concise. It has to have make them understand what you did, what you found and what they need to do about it. The more pictures, screen shots, graphs and middle-school-level language, the better. They aren’t dumb, or ignorant, they just have other work to do and need the information they need to action against in the cleanest, clearest and fastest way possible. They don’t want to Google technical terms and they have no patience for jargon. So, say it clear and say it in the shortest way possible if you want to be the best penetration tester they’ve seen. 

That’s hard to swallow. I know. But, you can always jump on Twitter or Slack and tell us all about your L33T skillz and the newest SQL technique you just discovered. Even better, document it and share it with other testers so that we all get better.

Lesson 3: Penetration tests aren’t always useful. They can be harmful.

Lastly, penetration tests aren’t always a help. They can cause some damage, to weak infrastructures, or to careers. Breaking things usually comes with a cost, and delivering critical failure news to upper management is not without its risks. I’ve seen CIOs and CISOs lose their jobs due to a penetration test report. I’ve seen upper management and boards respond in entirely unkind and often undeserved ways. In fact, if you don’t know what assets your organization has to protect, what controls you have and/or haven’t done some level of basic blocking and tackling – forget pen-testing altogether and skip to an inventory, vulnerability assessment, risk assessment or mapping engagement. Save the pen-testing cost and dangerous results for when you have more situational awareness. 

Penetration testing is often good at finding the low water mark. It often reveals least resistant paths and common areas of failure. Unfortunately, these are often left open by a lack of basic blocking and tackling. While it’s good news that basics go a long way to protecting us and our data, the bad news is that real-world attackers are capable of much more. Finding those edge cases, the things that go beyond the basics, the attack vectors less traveled, the bad assumptions, the short cut and/or the thing you missed when you’re doing the basics well – that’s when penetration tests have their biggest payoffs.

Want to talk more about penetration testing, these lessons or finding the right vulnerability management engagement for your organization? No problem, get in touch and I’ll be happy to discuss how MicroSolved can help. We can do it safely, make sure it is the best type of engagement for your maturity level and help you drive your security program forward. Our reports will be clean, concise and well written. And, we’ll pay attention to the details, I promise you that. 🙂 

To get in touch, give me a call at (614) 351-1237, drop me a line via this webform or reach out on Twitter (@lbhuston). I love to talk about infosec and penetration testing. It’s not just my career, but also my passion.

Podcast Episode 2 is Now Available

In this episode we sit down with Mark Tomallo, from Panopticon Labs, and RSA’s Kevin Flanagan. We discuss mentoring, online crime, choosing infosec as a career and even dig out some tidbits from Mark about online gaming fraud and some of the criminal underground around the gaming industry. I think this is a very interesting and fun episode, so check it out and let us know what you think on Twitter (@microsolved, or @lbhuston). Thanks for listening! 

Listen Here:

Podcast Episode 1 is Now Available

This episode is about 45 minutes in length and features an interview with Dave Rose (@drose0120) and Helen Patton (@OSUCISOHelen) about ethics in security, women in STEM roles and career advice for young folks considering Infosec as a career. Have feedback, let me know via Twitter (@lbhuston).

 
As always, thanks for listening and reading stateofsecurity.com!
 
Listen here: 
 
PS – We decided to restart the episode numbers, move to pod bean.com as a hosting company and make the podcast available through iTunes. We felt all of those changes, plus the informal date-based episode titles we were using before made the change a good idea.

Young IT Professionals, Cybercrime, Script Kiddies & CyberWarriors, OH MY!

Recently I came across a couple of articles that both centered on the potential roles that young people entering into the IT Security field may face. Some of them, for example, may be lured away from legitimate IT security jobs and into the world of cybercrime. Others may follow the entrepreneurial role and fight cybercrime alongside myself and other professionals.

I suppose such dichotomies have existed in other professions for quite some time. Chemists could enter the commercial or academic world or become underground drug cartel members, ala Breaking Bad. Accountants could build CPA tax practices or help bad guys launder money. Doctors could work in emergency rooms or perform illegal operations to help war lords recover from battle. I suppose it is an age old balancing act.

I am reminded of Gladwell’s Outliers though, in that we are experiencing a certain time window when IT security skills are valuable to both good and bad efforts, and a war for talent may well be waging just beyond the common boundary of society. Gladwell’s position that someone like Steve Jobs and Bill Gates could only emerge within a specific time line of conditions seems to apply here. Have we seen our IT security Bill Gates yet? Maybe, maybe not….

It is certainly an interesting and pivotal time isn’t it? These articles further solidified my resolve to close a set of podcast interviews that I have been working on. In the next couple of months I will be posting podcast interviews with teams of IT and Infosec leaders to discuss their advice to young people just entering our profession. I hope you will join me for them. More importantly, I hope you will help me by sharing them with young people you know who are considering IT security as a career. Together, maybe we can help keep more of the talent on the non-criminal side. Maybe… I can always hope, can’t I? 🙂

Until next time, thanks for reading, and stay safe out there! If you have questions or insights about advice for young security professionals, hit me up on Twitter (@lbhuston). I’ll add them to the questions for the podcast guests or do some email interviews if there is enough interest from the community.