Ask Lesley InfoSec Advice Column: 2017-03-16

This week, I address some burning questions about education and training.  As always, submit your problems here!

Dear Lesley,

Let’s cut to the chase. I hate coding. I don’t enjoy building things from scratch. I do, however, love taking things apart, and would probably be able to learn to code if I started in that direction.

I currently work as a Linux sysadmin in the web industry, with a couple certs (and 4 years) under my belt so far. I love infosec and want to move in that direction, but I have no idea where to start, given my utter distaste for traditional methods to teach coding.
Do I just… download some arbitrary code and take it apart? That seems like a horribly insecure idea, but I’m just not sure where to start. I also tend to have serious issues with confidence in everything, especially tech. Please help! ”    

– Flustered and floundering

Dear Flustered,

I don’t like coding, either. It’s actually not uncommon in infosec – we tend to like rapidly changing environments instead of the routine patience involved in coding. I’ve spoken to many ex-programmers and ex-CS students who agreed.

I see two routes you can go if you think anything like me:

  1. The scripting route: Many, many blue team and red team tools are Python and Ruby based, and many of them are extensible by design. Pick offensive or defensive security, then choose a tool set in one of these common languages that interests you. (For me, it was the Volatility framework). Take apart a few existing scripts and see how they function in real life. Then pick some interesting feature to add in your own script. This won’t necessarily teach you how to write a stellar production application, but for most security roles scripting is what you need.
  2. The reversing route. If analyzing malware piques your interest, that’s a great way to learn how software works all the way down to the assembly level. The intrigue can be a great motivator to learn. Definitely don’t pick commodity malware out today to analyze -it’s purposefully hard to reverse! Start with a book like Practical Malware Analysis or Malware Analyst’s cookbook that has detailed, step by step tutorials from the very basics. Learning how to take something apart can be a great way to learn how to put it together, and you’ll definitely figure out what fundamentals you need to brush up on on the way.

Dear Lesley,

Looking into the future…what would you guess would be the safest career path/area to focus on now in security, considering the growth in available off the shelf tools to get the jobs done. Would penetration tester still be needed for example in 10-20 years time?  

–  Spinner.

Dear Spinner,

First off, no guarantees – I’m not clairvoyant. There definitely is something of an infosec bubble as more people enter degree programs. However, there’s a caveat – being a great hacker is a personality trait, not a skill that can be taught academically. If you’re innovative and adaptable, I sincerely doubt you’ll have trouble finding work in that time frame.

In terms of automation, some tasks automate better than others. Unfortunately, the one that automates the best is the entry level security analyst gig. Merely passing the Security+ and being able to read and route SIEM events may not cut it in a couple years. You’ll need creativity and a broader skill set. More advanced defensive and offensive roles will require human attention for the foreseeable future because attackers innovate constantly. While a magic black box may pick up a new zero day, remediating and understanding the impact and additional factors is more complicated.

Security engineering continues to become more automated. The need for people to simply maintain static blocklists, signatures, or firewall rule sets will continue to decrease. Those jobs are trending towards more advanced SIEM and log aggregation management.

The jobs I see in the most demand with the least supply right now are malware reversing at an assembly level, threat intelligence with an actual political science or foreign studies background, and higher level exploit research (coupled with good business and communication skills).

Dear Lesley,

How does one begin exploring the world of sec without coming off as a script kiddie or just wanting to be an “edgy hacker”?     

– Careful but eager beaver

Dear Careful but Eager,

I’m really sad you feel that you have to ask that question, because merely asking it means you probably aren’t the type you’re concerned about. How do you know if you’re skidding it up? You enter commands into a hacking tool with no idea what they are doing, and much more importantly, no interest in knowing what they are doing. Being a good hacker has nothing to do with pwning stuff. It has to do with understanding how lots of stuff works and being able to manipulate that to your advantage.  (I should put that at the top of my blog in huge red letters!)

Imagine you’re a secret agent, needing to break into a vault. You can take one other person with you. Person 1 is another agent who has read a few books on how the vault works. Person 2 is the engineer who has been installing and maintaining the vaults for 30 years and has agreed to help you. Who do you pick? I’d pick the second person, who knows the system inside and out. I can teach her to sneak around a little and how to wear a disguise. Person 1 doesn’t know the foibles of the vault and only knows how to attack it the way the books said.

To summarize, you skid check is how many commands you enter in Kali or Sift or whatever without bothering to figure out what the heck you are doing. When you’re learning, the goal is understanding that, not getting a shell.

You shouldn’t care what you come off as. If you’re genuinely interested in learning, plenty of hackers will be willing to help you.

Dear Lesley,

(tl;dr at the very last line)

I am a novice who is looking to break into the field of security. Currently, I have received an offer to read a book (The Web Application Hacker’s Handbook) and participate in an assessment to show if I can perform the work necessary to do the job. Essentially, the assessment (from what I’ve gathered) is to assess the security of a vulnerable web application and then reverse a protocol.

Coming from a mathematics background with limited formal education in computer science and no formal education in networking, the book is hard to digest. I have setup pen test labs such as DVWA and WebGoat which I am practicing with and I have made surprisingly good progress in these labs. I’ve also learned a little bit about networking through much trial in error in setting these labs up in safe environments!

However, I fear that even if I pass the assessment, I will not be offered a position due to my lack of networking knowledge. I am aware of certifications such as OSCP and Security+ to bolster my background, but they suggest a solid understanding of networking before enrollment in the courses or studying for the examinations.

Do you have any recommendations on books/courses/certifications that would take an individual from zero-knowledge of networking to the suggested level of networking knowledge for these kinds of security certifications?

– Not a smart man

Dear Smart Man (I refuse, because it’s untrue!),

It really sounds like you’re doing everything right. You have correctly recognized that solid TCP/IP knowledge is really important in security. The lab is fab. But, you can do other things in that lab. Like take a step back from the security tools, and concentrate on the networking ones. How long have you spent in Wireshark, just observing and filtering through network traffic? Something just watching what’s going on and identifying common ports and protocols can be huge. What does opening a website look like, and why? What does a ping look like? What does it look like when a new computer is connected to the network?

Certs (and associated books)… There are a lot of options in network land. Network+ is okay for fundamentals and really cheap (although an inch deep and mile wide). WCNA is the Wireshark specific cert, but by nature teaches a pretty in-depth level of knowledge of reading packets. It’s also quite affordable. If you have 600 bucks and free time, I’d do both (in that order) and blow those folks out of the water with your resume. If you don’t have those resources, they give you some great study materials to start with.

There are endless good books and blogs on TCP/IP out there that will get you started and give you an understanding of the OSI model and common ports and protocols. Hands on experience in your lab or on your home network  is much more important.




Ask Lesley InfoSec Advice Column: 2017-02-26

This week, we discuss red team and blue team self-study, getting kids interested in security, and security paranoia. As always, submit your problems here!

Dear Lesley,
I am a threat intelligence analyst who is currently underutilized in my current job, and feel like my skills and tradecraft are slipping because of it. I’m wanting to give myself some fun projects to work on in my off-time but am not really sure where to start. What types of things would you recommend?

Dear M,
You’re certainly in a great field to want work in, in 2017. Not only do you have the whole pantheon of nation state actors conducting cyber operations to study, but you have a huge range of commodity malware, botnets, insider threats, malware authors, and dark web markets to study.  If you’re not feeling inspired by anything in that list, perhaps reach out on Intel sharing lists or social media to see if an existing project could use your skill set? Lots of folks are doing non-profit threat research work and need extra hands.

Dear Lesley,
If you do not have the budget to send people to SANS or to conferences, what free supplement resources would provide fundamental training for someone studying DFIR?  
-Curriculum Writer

Dear Curriculum Writer,
I can totally appreciate not being able to send somebody to a thousand dollar (or more) commercial conference or training program. However, most BSides conferences are free (or under 20 dollars). I suppose if you are totally geographically isolated and there is no BSides in any city in driving distance, those may be impossible, but I would definitely explore the conference scene in detail before writing them off. Sending somebody to a BSides or a regional conference for the cost of gas and a few bucks provides a lot of value for the money.

Otherwise, a DFIR lab will be your best friend for self study. Unfortunately, I can’t guarantee a home lab will be totally free to implement. Let’s talk about some fundamental requirements:

– One or more test hosts running assorted operating systems.
– An examiner system running Linux
– An examiner system running Windows (recommended)
– Intermediate networking
– Free (or free non-corporate) forensics and malware analysis tools.
– A disk forensics suite
– A memory forensics suite
– A write blocker, associated cables, and drives.

An ideal comprehensive DFIR lab, where money is no object, might look something like:

– A host PC with 16GB (or more) RAM.
– VMWare Workstation
– Ubuntu (free), Windows 7, 10, and Server 2008 VMs
– A SANS Sift Kit examiner VM (free)
– A REMnux Kit examiner VM (free)
– A Cuckoo Sandbox VM (free)
– A Server 2k8 examiner VM
– An EnCase or FTK forensics suite license
– A write blocker, associated cables, and a number of hard drives.

But, we can do it more cheaply, sacrificing convenience. We can virtualize with VirtualBox (losing the ability to take non-linear, branching snapshots), or on bare metal machines we scrounge from auctions or second hand stores (the least optimal solution). This can work, but every time we infect or corrupt a machine, we’ll have to spend time restoring the computers to the correct condition. We can stick with analyzing Windows versions that are out of support, but we won’t be totally up to date.

One of the most difficult things for people studying the “DF” side of DFIR is the inability to get expensive licenses for industry-standard corporate forensics suites. There’s really no great solution for this. There are limited demo versions of this software that come with some forensics textbooks. SANS Sift Kit does include The Sleuth Kit, an open source suite which performs some similar functions.

Physical forensic toolkits aren’t cheap, but aren’t in the same ludicrous territory as forensics software. You can pick up an older used Tableau forensic bridge for about 150 dollars on eBay. Perhaps if you network within your local security meetup, somebody will be able to lend you one, as many college and training courses provide them.

Once we have something resembling a lab, we can follow along with tutorials on SecurityTube and on blogs, in forensics and malware reversing textbooks, in open courseware, and exploring on our own.

Dear Lesley,
I have a daughter that I would like to encourage her to go into IT and possibly security if she’s interested. I know your father was influential to you getting into security. Do you have any suggestions to me as a dad on things I can do to encourage my daughter to become interested in IT and security?
-Crypto Dad

Hi Crypto Dad,

Yep, both of my parents had a big influence on my career! A hard question to answer, but an important aspect was not pushing me hard towards or away from hobbies. I was treated like a small adult and provided the opportunity to follow along with whatever my dad was doing in his shop, and even at a very young age he answered my questions without patronizing me or getting frustrated. He didn’t dumb things down; he just started at the beginning. I always had access to stuff to learn how it worked and how it was made. By the time I found out I ‘wasn’t supposed to’ know or like things , I already knew and liked them.

Dear Lesley,
I’m a penetration tester who seems to be falling behind with the times. My methods aren’t efficient. Recently I discovered there are better ways of doing things than my three year old SANS curriculum taught me. How can I stay current without becoming a lonely crazy old cat lady?
-Just a crazy cat lady

Hi Crazy Cat Lady,
You’re ahead of many folks by realizing there’s a problem. I see a lot of infosec people let their skills stagnate for many years after training or college, and our field changes really fast. No quick fix, but here are some suggestions:

– Participate in CTFs. Ignore the scoreboard and the dudebros and “rock stars”. Just compete against yourself, but do it genuinely and learn from your mistakes.
– Jump over to the blue team side for a bit and read some really thorough incident and threat reports from the past couple years. Sometimes seeing what other people are doing will give you interesting ideas of avenues to research.
– If you’re still reaching for Kali, escape its clutches. Kali is an amazing VM, but it will only take you so far and lacks some newer tools. It can also discourage thinking “out of the box” about how to compromise a network. After all, it is a box.
– Get out to cons to watch red team talks. Watch recent ones on YouTube, too. See what other folks are up to. Your cats will be okay for a couple days, and you’ll make new friends.
– PowerShell Empire. 💖💖💖
– Don’t be embarrassed to make mistakes and ask questions.
– Don’t be embarrassed to make mistakes and ask questions.
– Don’t be embarrassed to make mistakes and ask questions.

Dear Lesley,
How do you deal with any overbearing paranoia being in InfoSec? Example: I want my home network to be as secure if not more than my work network… How can I explain my paranoia regarding outside threats (however unlikely), and to cope with it 🙂
-Too Paranoid to enter my name

Hi Paranoid,

Fear is healthy in small doses. Fear keeps us alert to potential threats, and helps us survive dangerous situations. However, constant fear is not helpful and is patently unhealthy. If you see illusory threats in every dark corner, you won’t notice when a real one is there, and you’ll be too tired to respond properly to it.

You need approach this as analytically as you can. Let’s talk about measuring real risk.

– Evaluate your assets. What would somebody genuinely target you for? This isn’t necessarily items or information, but could also include your job position or connections.
– Evaluate real threats to you. Who rationally has motive to “get you”, and do they have the means and the opportunity to?
– Evaluate your vulnerability. How could somebody attack you or your assets, and how much effort and resource would it take to do it? How well do you mitigate vulnerabilities? Are you a harder target than others facing similar threats?

Risk is a direct result of the level of threat against you and your assets, and your vulnerabilities. It’s impossible to change the level of threat. All one can do to change risk is change assets, or change vulnerabilities.

People make personal decisions about acceptable risk. A firefighter lives with a different level of risk than a librarian. The firefighter likely has to deal with occasional moments of quite rational fear and adrenaline (due to actual threats and vulnerability), but does not live in constant fear of burning buildings. The librarian might consider running into burning buildings an unacceptable level of risk, which is why he found a less risky profession. However, both people live comfortable with their overall risk and their mitigations, and not in irrational fear.

With all this in mind, consider the things that you’re paranoid about carefully. What is the real level of risk each poses? What level of real risk will you choose to accept on a daily basis? If your overall level of risk is actually too high to cope with on a daily basis, reduce your targeted assets, or reduce your vulnerabilities. If you find your level of risk acceptable, then maintain that level rationally and try not to be unduly afraid. You likely have more to fear from chronic health problems than nameless threats.

Ask Lesley InfoSec Advice Column: 2017-01-30

Thanks for another wonderful week of submissions to my “Ask Lesley” advice form. Today, we’ll discuss digital forensics methodology, security awareness, career paths, and hostile workplaces.


Dear Lesley,

I’m a recent female college graduate that didn’t study computer science but is working in technical support at a software company. The more I learn about infosec, the more curious and interested I get about if this is the field for me. What do you resources/videos/courses/ANYTHING you recommend for people who want to make a serious stab at learning infosec?

– Curious Noob

Dear Curious,

I’m really glad to hear you’re discovering a passion for infosec, because curiosity is really the most fundamental requirement for becoming a good hacker. I wrote a long blog series about information security careers which I hope you may find helpful in discovering niches and planning self-study. For brevity’s sake, here are some options for you.

  • Study up on any fundamental computer science area you’re underexposed to in your current work – that means Windows administration, Linux administration, TCP/IP, or system architecture. You need to have a good base understanding of each.
  • Get involved in your local CitySec, DEF CON local, or 2600 meet up group. They are great networking opportunities and a fabulous place to find a mentor or people to study with. There are meet ups all over the world in surprising places.
  • Consider attending an infosec / hacking conference. The BSides security conference in the nearest major city to you is a great option and should be very affordable (if not free). Attend some talks and see what speaks to you. Consider playing in the CTFs or other security challenges offered there, or at least observing.
  • Security Tube and are your friends, with massive repositories of conference talk videos you can watch for free. Nearly any security topic that piques your interest has probably been spoken about at some point. I would favor those sites over random YouTube hacking tutorials which really vary in quality (and legality).
  • Consider building your own home lab to practice with basic tools and techniques. Networked VMs are adequate as long as you keep them segregated: Kali Linux and a Windows XP VM are a great place to start. You need to take stuff apart to learn about hacking.

These are only some brief suggestions – there’s no streamlined approach to becoming a great hacker. Get involved, ask questions, and don’t be afraid to break stuff (legally)!

Dear Lesley,

What do you do when you provide security awareness training to your employees, but they still click on phishing links!

– Mr. Phrustrated

Dear Phrustrated,

Beyond generally poor quality “death by PowerPoint” training, one of the biggest problems I see in corporate security awareness programs is poor, unsustainable measures of success. For instance, it’s become really trendy to conduct internal phishing tests to identify how many people click on a phish. It’s incredibly tempting to show off to executives that this number is trending down, but that metric is really pretty worthless.

No matter how ruthlessly trained, somebody (and anybody) will click on a well-enough crafted phish, and it only takes one compromise to breach a network’s defenses. What we should be measuring is the reporting of phishing messages and good communication between employees and the security team. The faster we know an attack is underway, the faster we can respond and mitigate the threat.

In conclusion, you should be less concerned if “somebody is still clicking” phishing messages than if nobody is telling you they clicked, and they resist or lie in embarrassment when asked.

Dear Lesley,

Is there a mental checklist while doing digital forensics to not make your evidence point to your quick conclusions, even if you think you have seen a similar case?

– Jack Reacher Jr.

Dear Jack,

Identifying that this is a problem is a great first step. While intuition is an important part of being a good investigator, sound methodology is even more important. The checklist you use to collect evidence and perform an investigation is going to vary by where you work and what types of things you investigate, but you should always have and follow a checklist – and I recommend it be a paper checklist, not mental.

Don’t ever shortcut or skip steps, even when you’re in a high pressure situation. Shortcuts and assumptions are incredibly dangerous to the legal and technical validity of investigations. Gather all the facts available to you at the time, and document ever step you take so that a colleague (or a legal professional) can follow your work even far in the future.

Finally, always remember that in a digital forensic investigation we are generally providing evidence to reach conclusions about “what, when and how”. “Who” is shaky ground, because in most cases it involves context outside the digital device. “Why” is almost never the business of a forensic analyst (and is indeed often not within the capacity of a company to responsibly answer). If you find yourself looking for evidence to fit a presumed “why” scenario, you have a big problem and you need to step back.

Dear Lesley,

I’m this girl like I said, who just started working in the field, and for the past 4 months, I worked at this huge corporation, who has, among other services, an information security related one, offering technical security (pen testing, …) and non-technical security services. At that time, I had little information about advanced hacking techniques as well as the good practices that should be followed to secure our systems.

During the first weeks I got hacked by someone who’s working with me, and I was harassed and shamed by them since then. I knew it because this person would talk about their findings to everyone, even to non-technical people, in the corporation. People would look at me and laugh, smile, smirk, or look at me pathetically, in addition of other situations.

Knowing that this person is an expert (12 or more years working in information security) and that I don’t have any proofs on their actions, what should I do in your opinion ? What kind of advice would you give to girls and women like me, who want to work in the field but get harassed by their experienced co-workers instead of being encouraged by them ?

– I

Dear I,

Your story gave me pause enough to discuss it substantially with several colleagues in information technology who have also worked in extremely hostile environments.

This is a horrific situation. I want to make it crystal clear that this is utterly shameful on the part of your employer, your infosec colleagues, and your organizations’ corporate culture. I truly hope it does not drive you from our field. The most important thing I can tell you is that this is not your fault. and this is not normal.

The first thing I recommend you do is document everything that’s happening in as much detail as possible, even if you don’t feel you have evidence right now. The activity you’re talking about may not only be harassment, but violate hacking laws. Since device compromise is a concern, please maintain this documentation offline.

What you do next depends on factors you don’t mention in your note. First of all, if you have a trusted supervisor, manager outside your team, or senior mentor in your organization, please turn to them for assistance and ensure they are corroborating what has been happening to you on paper. It’s their responsibility to assist you in resolving the issue at a work center or corporate level, even if they’re not directly in your reporting chain.

If there’s nobody at all you can go to in confidence, the situation becomes substantially more unpleasant. Your options are to ignore the behavior to stick out the requisite ~2 years of entry level security at the organization(obviously the worst option), seek employment elsewhere, or contact an HR representative (with the risk of retribution and legal battles that can bring). Obviously, my personal recommendation is taking you and your computer straight to HR. As a wise colleague of mine pointed out, this is most likely not an isolated incident – the behavior and dismal culture will continue for you and others. Sadly, in some places in the world with less employment protections, this can carry the risk of termination. Keep in mind that it is okay to confidentially consult a lawyer within the terms of your employment contract, and pro bono options may be available.

If HR / legal action is not an option, you can’t find employment elsewhere, and you’re toughing it out to build entry level experience, please network and find a local mentor and support structure outside of your company as soon as possible. As well as much needed emotional support, these people could help you study, network, bite back, and explore other recourse against the employer. Feel free to reach out to me anonymously and we’ll try to connect you with somebody in your area.


Ask Lesley InfoSec Advice Column: 2017-01-19

Thanks for your interesting question submissions to “Ask Lesley”! This column will repeat, on no specific schedule, when I receive interesting questions that are applicable to multiple people. See further details or submit a question, here. Without further ado, today we have OS debates, management communication issues, nation state actors, and career questions galore!

Dear Lesley,

So last year’s Anthem breach was from a nation state – why would a nation state want to hack health insurance info? I understand the identity theft motivation of a criminal, but why do you think a nation state would want this type of data?

– Inquisitive

Dear Inquisitive,

First off, I can’t confirm the details of the Anthem breach – I wasn’t involved in the investigation and haven’t had the privilege of reviewing all the evidence. However, when generally talking about why a state-sponsored actor might want to acquire data, you have to look at a bigger picture than data sets. Nation states usually view hacking as a means to an end. They (ab)use data with a firm political or military objective in mind. Whether a nation state intended to steal 80 million records, or the theft was a crime of opportunity when looking for something more specific, what they stole may unfortunately be useful to them for years to come.

You can obviously already see how the data stolen in a healthcare breach is a treasure trove for general identity theft. The piece I believe you might be missing considers how the data could be combined with other public domain and stolen information to facilitate political objectives. If you already have a target in mind, healthcare data could be a great boon to social engineering, blackmail, and surveillance efforts. For example, consider how much leverage knowing that a target’s child is ill could provide. Or that a target family is hundreds of thousands of dollars in medical debt. These are attractive attack vectors. I can only speculate on potential scenarios, but based on my experience in OSINT, the data stolen from Anthem adds attractive private information about many millions of people.


Dear Lesley,

The ‘researcher’ portion of ‘security researcher’ implies graduate school – is PhD study in cybersecurity worth it? There doesn’t seem to be many programs that are worthwhile (except on paper only)

– Not in Debt, Yet

Dear Not in Debt, Yet,

That’s an interesting implication – not one I necessarily agree with based on empirical evidence. I know full time, professional security researchers studying everything from exploits to governance who have every level of formal education, from GEDs to PhDs.  I do see certain fields of security research represented in higher education more than others – a couple examples are high level cryptography and electronic engineering.

I have always been an advocate for higher education and I see little harm and many benefits in getting a good education in a field you enjoy (particularly, a well-rounded education) if you can afford it. However, at the present, there are very few information security careers or communities of research which require a degree, and fewer good quality degree programs. You should see few credential-related barriers to participating in or publishing security research if your work and presentation is good quality.

In some ways, existing exclusively in academia can also make it harder to work in practical security research, as the security field changes more quickly than university curricula can keep up. As a result, some academic security research ends up impractical and theoretical to a fault. (See my yearly rants on steganography papers.) If you go the academic route, choose your field of study carefully, and be careful not to lose touch with the working world.

Dear Lesley,

While working on my 5 BILLION dollar data breach, I wanted some blue cheese dip and chips (The Spice House in Chicago has the best mix btw), a co-worker looked at me with disgust. Am I wrong? Also what’s a good resource to learn about file carving?

– Epicurean EnCE

Dear Epicurean,

Clearly, your coworker is a Ranch dressing fan and should therefore be looked upon with disdain. In regards to file carving, your mission, (should you choose to accept it), is to review how files are physically and logically stored on a hard drive. Next, you’ll want to start familiarizing yourself with typical file headers and footers. Gary Kessler has a pretty killer list, here. Some file types will be more relevant to your specific work in forensics than others; I can’t tell you which those will be.  Your best bet is to pick a couple file types you look at a lot and look at them in a hex editor, then start searching for them in a forensic image.

Brian Carrier’s File System Forensics book, while a bit older, is still a stellar resource for understanding How Disk Stuff Works. SANS SIFT kit includes the tools you will need to get started carving files from disk, and the associated cheat sheets will help with the commands.

If you want to carve files from packet captures, similar header/footer knowledge is required, along with a different tool set. Wireshark’s export alone will often suffice; if it fails, look at Network Miner.

Dear Lesley,

What was the silliest / dumbest thing you’ve googled this week?

– Curious in Cincinnati

Dear Curious,

“The shirt, 2017”

I still don’t get what’s up with that.


Dear Lesley,

I teach high school computer science courses and many students biggest interest is infoSec stuff. What should they do to prepare at that age? Any recommendations on software or skills I can teach them? I’m willing to put in the time and effort to learn things to teach and we have class time, but this isn’t what my tech career focused on so I need some help. Thank you, you’re the best!

– Mentor in Michigan

Dear Mentor,

Being a crummy hacker requires learning to use a few tools by following YouTube. Being a good hacker requires a great deal of foundational knowledge about other, less entertaining computer stuff.

The better one knows how computer hardware, operating systems, and networks work, the better he or she will be at hacking. If kids come out of your classes unafraid of taking their own software and hardware apart, you did your job right. That means a lot of thinking about how Windows and Linux function, how computer programs work all the way down to Assembly, and how data gets from point A to point B. If you are going to encourage kids to take stuff apart, make sure they also understand that law and ethics are involved. Provide them a safe and legal sandbox to explore, and explain why it’s important to know how to break things in order to fix them.

As an aside – by high school, kids are more than old enough to be actively participating in the infosec community if they wish. Numerous kids and teens attend and even present at hacker events, these days; in fact, many conferences have educational events and sponsorships specifically for youth.


Dear Lesley,

 I normally use a Chromebook, but I also have to use Windows 10 so that I can use Cisco packet tracer (I’m studying CCNA). I really trust the security of my Chromebook, but Windows 10 – not so much. I have antivirus, anti-exploit and anti-ransomware software on my Windows laptop. But my question to you is: Is there a resource that you know of that can help lock down Windows 10 for the home user? Most of what I find is for enterprises and Enterprise versions of Windows 10 and if I do find something for the home user it invariably talks about privacy rather than security.

–  Kerneled Out

Dear Kerneled Out,

The OS wars, while somewhat befuddled by 2016, are alive and well. There are dogmatic Linux fans, and dogmatic Windows fans, and so on and so forth. My opinion is that every OS has its place when used correctly by the right person. Many serious security people I know use every major OS on a daily basis – I sure do.

Swift On Security has a nice guide here on securing Windows 10 that should suit your needs.

As for Chrome over Windows – please don’t fall into the “security by obscurity” trap that MacOS and Chrome can encourage. They are both solid OSes with interesting ideas on security, and viable choices for home and business use cases. However, modern versions are not inherently more or less secure than modern Windows. MacOS, Windows, Chrome, and major Linux distros are as secure as they are configured and used by human beings. Of course, the complexity of configuring them can vary based on user experience and training.


Dear Lesley,

How come everyone wants 5 years experience for an entry level infosec job? I’ve been trying to get gainful employment in an offensive role for more than 6 months and no one wants anyone with less than 5 years of pentesting/red teaming experience. Can’t exactly do pen tests until you’re a pentester, so what do I do?

– Frustrated

Dear Frustrated,

I’m sorry to hear you’re having so much trouble finding a position. I have written quite a lot about infosec career paths and job hunting in previous blogs, and I hope that they can assist you a little. Red teaming is unfortunately much harder and more competitive to find work in than Blue teaming, so my suggestions here are not going to be particularly pleasant:

  • Consider your willingness to move. There are simply more red team jobs in places like DC and the west coast.
  • Consider if you can take a lower-paid internship. It sucks, but it’s an in, and pen testing firms do offer them.
  • Consider doing blue team SOC work for a couple years. It’s not exactly your cup of tea, but it will give you solid security experience.
  • Network like crazy. Get to the cons and the meet-ups in person. Talk to people and build relationships.
  • Do research and speak about it. Pick something that intrigues you, even if you have no professional experience, and do a few months work, and submit to a CFP. It will get you name recognition.

Dear Lesley,

Many infosec professionals feel that signature-based antivirus is dead. If that is the case… What do you recommend we replace it with to protect our most vulnerable endpoints (end users) with?

– Sigs Uneasy

Dear Sigs,

That’s the kind of black and white statement that makes a good headline, but exaggerates the truth a bit. Yes, there are a couple companies who have been able to ditch antivirus because of their topology and operations. The vast majority still use it. While signatures alone don’t cut it against quickly replaced and polymorphic threats, other antivirus features, such as HIPS and heuristics, still provide a benefit. (So, if you’re still using some kind of antivirus that can’t do those things, it’s time to upgrade.)

Antivirus today is useful as part of a “defense in depth” solution. It is not a silver bullet, and it’s certainly defeatable. However, it still catches mass malware and the occasional targeted threat. The threats AV misses should be caught by your network IPS, your firewall, your web filters, your application whitelisting solution, and so forth. None of those solutions is bulletproof alone, and even the efficacy of trendy solutions like whitelisting is limited if you don’t architect and administer your network securely.

Dear Lesley,

I was testing a network and found some major flaws. The management doesn’t seem too bothered but I feel the issues are huge. I want to out them because these flaws could impact many innocent people. But if I do, I won’t be hired again. I look forward to your response.

– Vaguely Disturbed

Dear Disturbed,

Before whistle-blowing and potentially getting in legal trouble, I highly recommend you approach this argument from a solid risk management perspective. Sometimes, “it could be hacked” means a lot less to management than, “9 companies in our industry were breached in 2016, and if we are, it will probably cost us over 70 million dollars in lost revenue”. If you have access to anybody with a risk analysis background you can reach out to under the relevant NDA, I highly recommend you have a chat with them and put together a quantified, evidenced argument, ASAP. The more dollar signs and legal cases, the better your chances of winning this.

At the very least, win or lose, ensure you’ve covered your butt. This means written statements and acknowledgements stating you clearly explained the potential risk and also that they willfully chose to ignore it. Not only does requiring a notarized signature make the appearance of threat go up, but it will be helpful in case they decide to blame you or your employer two years from now.

I would suggest you consult a lawyer before breaking NDA or employment contract by whistle blowing, no matter how noble your intentions. I am not a lawyer, nor do I play one on TV.

Dear Lesley,

I make software and web applications that connect to software and services from other companies. Sometimes those companies disable or cripple some features due to possible security exploits. When I’ve met with security people from those companies and asked them about the features they nerfed (disabled or crippled), I’m met with an awkward silence similar to the vague errors I get from their servers. As a developer, I’m so used to the open-source community that wants to help that this feels weird. Is there some certification, secret handshake, or specific brand of white fedora I need to have conversations with security people about their products security issues? Just trying to learn and grow, and not cause a mess for anybody.

– Snubbed

Dear Snubbed,

No secret handshake. Here are a couple suggestions from the receiving end of these types of concerns:

  • Set up a security lab with your applications and a client on it. Install a Snort or Suricata sensor(s) with the free Emerging Threats ruleset in the midst of them to intercept their communication. (Security Onion is a nice, relatively easy to install option.) Send normal application traffic back and forth and see what security signatures are firing on the network.  That will give you some idea of what might be getting blocked before you even start the discussion (and help you reduce false positives).
  • Ensure your applications are getting proper vulnerability testing before release. Again, even if you’re coding securely and responsibly, this can help reduce false positive detection by vulnerability scanners or sensors.
  • Ask the security people what security products or appliances they are using on the hosts and on the network, and what signatures are firing. You might not have access to a 20,000 dollar security appliance to test, but their sensor might have full packet capture functionality or verbose logs that will help you troubleshoot.
  • Try to build a better professional relationship with these teams if you can. If they’re involved in a local security group, perhaps drop by and have a drink with them.


Dear Lesley,

I’m feeling it is time to move on from Windows XP, but only because many things no longer support it, and 3Gb is a bit limiting when running VMs and the like. I’ve tried Windows 10, and it is completely alien, and I worry about security – it streams things back to Microsoft, and is less secure than my hardened XP install. I’ve tried Mint Linux, and that was quite good, but underneath it is even more alien than Windows 10. I’ve heard of BSD, but I’m worried that my political career could be over if word about that got out, so I’ve not tried it. What do you suggest?

– Unsupported in UK

Dear Unsupported,

It is indeed high time to move off XP.

Windows XP is unsupported, highly vulnerable, and trivially exploitable by hackers. It is not in the same league as Windows 10 in terms of security. Even application whitelisting (which is considered a bit a last resort silver bullet in industry) isn’t a reliable means of securing XP against attacks anymore.

Yes, there are some IT professionals who dislike Windows 10. Those concerns usually have to do with things like UI, embedded ads and system telemetry, not the underlying security (which is quite well engineered).

If those are your specific concerns, a current version of Mint (which you tried), Ubuntu, or MacOS are all okay options. They would all need to be thoughtfully configured for security just as much as Windows. BSD will feel just as unfamiliar if you were uncomfortable operating in Mint, but I certainly don’t discourage you from giving it a try. Even MacOS is *nix based under the hood.

Unfortunately, it seems to me that you’re stuck with two options if you want to maintain any semblance of security: cope with your dislike of Windows 10, or dedicate some time to learning the inner workings of a new operating system. Either way, please get off XP as soon as possible.

Dear Lesley,

My friend, since birth – who I’ll call M. E., has had a 23-year, jack-of-most-trades career in IT. ME is currently serving as the IT Decider (and Doer) at an SMB financial firm. Over the last five years, ME has enjoyed focusing on security. Technology, security in particular, is still near the top of his hobby list. However, compared to when he started his IT career, ME places a greater value on having a work-life balance. ME wonders if it’s too late for a change to the cyberz – without “starting over.” In your experience, is there a reasonable way for ME to jump from the “IT rail” to the “security rail” without touching the third rail and returning to Go, without collecting $200?

– ME’s Friend

Dear ME’s Friend,

Your ‘friend’ sounds like a great candidate for many security positions, but he or she might have to take a pay cut. 23 years of experience in systems administration and networking is 23 years of experience in how to take things apart, which is really mostly what security is behind the neat hats and the techno music.

ME is going to need to figure out two important things. Firstly, ME will need to gain some security-specific vocabulary to tie things together – a course or certification might be a nice feather in the cap. Then, ME is going to have to carefully plan out how to present him or herself as an Awesome Security Candidate in interviews and resumes. That will involve taking those 23 years of generalized experience, as well as security hobby work, and selling them as 23 years of Awesome Security Experience. For example, it takes a lot of understanding of Windows administration and scripting to be a good Windows pen tester. Or, it takes a lot of TCP/IP knowledge to do packet analysis of an IPS signature fire. Every niche of security requires deep knowledge of one or more areas of general IT.

All that being said, there are some security skills that need to be learned on the job. I wouldn’t push ME towards an entry level gig, but it may not be an easy lateral move to any senior technical position, either. A good segue if seniority is critical might be security engineering (IPS / SIEM / log aggregation administration, etc).

Dear Lesley,

How does an organization go about starting a patch testing program? Ours seems to be stuck in a “don’t update it, you’ll break the application” mindset. –

– TarPitted in Texas

Dear TarPitted,

As I noted to a reader above, sometimes this type of impasse with management can only be solved through presenting things as quantifiable risk. If you are telling management that your application is vulnerable, and they are saying it will cost too much if it breaks when you patch it, somebody else is quantifying risk better than you. You’d best believe that team saying, “the application might break” is also saying, “if this application breaks, it will cost us n dollars a day”. So, play that game. Tell management specifically how much money and time they stand to lose if a security incident occurs. Present this risk clearly – get help if you need to from all of the impacted teams, your disaster recovery and risk management professionals, and even your finance team.

Your managers should be making a decision based on monetary and other quantifiable business impact of the application going down for patching, vs. the monetary and other quantifiable business impacts of a potential security incident at x likelihood. Once they do that on paper, you’ve done due diligence.