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 Irongeek.com 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.

Best,
Lesley

Thwart my OSINT Efforts while Binging TV!

There’s been a bit of a social media uproar recently about the data collection practices of people search service FamilyTreeNow. However, it’s certainly not the first, only, (or last) service to provide potentially uncomfortable private information about people on the internet without their knowledge or consent. Even the most technologically disconnected people are frequently searchable.

In conducting OSINT research on people, services like FamilyTreeNow are often a gold mine, and are one of my first stops when I’m searching out useful facts to pivot into more intimate details about a target. Do you really want any casual stranger to know your home address, phone numbers, email addresses, and the names and ages of your kids? While disappearing from the internet completely can be nigh impossible, spending a little time removing easily accessible data can cause frustration and extra work for a nefarious (or nosy) person investigating you. I speak from experience. So, it’s worth taking some time to do, as we always want to make bad guys and gals’ lives harder.

So, grab a snack and a beverage, queue up a TV show to binge watch, and let’s make some quick and easy wins in helping you disappear from the malfeasant public eye. I’ll only ask you do five quick tasks per episode. You can do them during the boring parts.

Before we start, I highly recommend setting up a new webmail account to perform these removals. Almost all of the services require an email to opt out, and many require account registration. Since we’re dealing with firms that collect information about people, it’s sensible to avoid using your day to day or work email.

One last thing! It’s important to remember these services are not always accurate. You may have more than one entry for yourself at any of these services. Make sure to check!

Let’s begin!

  • Let’s get the aforementioned FamilyTreeNow out of the way. Their opt-out form is here: https://www.familytreenow.com/optout. They’ll require you to search for yourself through the opt-out page then click a red “opt out this record” at the top of your entry. (You must repeat this process from the start for every profile you wish to remove.)
  • Next, let’s head over to Instant Checkmate. Their Opt Out form is here: https://www.instantcheckmate.com/optout/ and requires you enter a name, birth date, and a contact email address.
  • We’ll head over to PeekYou, next, which requires you search their database first and provide the numeric profile ID in your page(s) URL, as well as an email address. Their opt out page is: http://www.peekyou.com/about/contact/optout/
  • Next up is Spokeo. You’ll once again need to search for yourself, but this time all you need to do is copy the full URL of your page(s). Then, head here: http://www.spokeo.com/opt_out/new, paste that link and enter your email address.
  • Let’s head to BeenVerified’s opt out page at https://www.beenverified.com/f/optout/search. Simply enter your name and location, select your entry or entries, enter your email, and click the verification link that is immediately sent to you.

SNACK, BEVERAGE, NEXT EPISODE BREAK!

  • So, Whitepages has two different types of profiles – free and paid, and they seem to have little to do with one another in terms of removal. For the free side, you’ll have to sign up for their service to remove entries, (which includes email verification). Once logged in, you simply need to paste the link to your entry here: https://secure.whitepages.com/me/suppressions.
  • For Whitepages Premium, you must open a quick support ticket with their help desk. Full details and the Help interface are here: https://premium.whitepages.com/help#about. You will need to copy and paste the link to your premium profile in the ticket (not the free Whitepages entry).
  • Let’s head over to PeopleFinders, http://www.peoplefinders.com/manage/. This one’s super easy; just use the search box to find your profile, and then click the opt-out button.
  • PeopleSmart is also relatively simple. Search for yourself at https://www.peoplesmart.com/optout-go. You will need to enter an email address and click a verification link.
  • USA People Search’s opt out page is here: https://www.usa-people-search.com/manage/ and simply requires clicking your profile and entering a captcha.

 SNACK, BEVERAGE, NEXT EPISODE BREAK!

  • Let’s head to Radaris, at https://radaris.com/. Search for yourself. Click “full profile”, then click on the down arrow to see the full menu of options. There is one that states “Control Information”. This will prompt you to register for an account with their service and claim your profile as yourself. Once you have done so, you will have the option to “Remove Information” or take your aggregated profile private, at any time.
  • The last information service we’ll tackle today is Peoplelooker, at https://www.peoplelooker.com/f/optout/search. Once again, a relatively easy opt-out process using a verification email.
  • Finally, let’s do a little social media cleanup!
    • If you have a Facebook account, perform a Privacy Checkup. It won’t take too long. Ensure your posts and likes are as private as possible.
    • If you use Google or YouTube services, perform their Privacy Checkup. Once again, ensure nobody but the right friends and family can see your activity.
    • Head to LinkedIn. On the header menu, select Privacy & Settings, then select the “Privacy” tab. Consider how much sensitive detail you are providing about your workplace, their tools and processes, and yourself. Consider restricting certain data on your profile to only connections and members.

Good work! Enjoy the rest of your snack and your show! Be proud that you’ve done some good work cleaning up your public presence, today.

***

It’s important to note that I’ve left a couple services out of this guide that are referenced in other comprehensive lists, (like this one), due to the complexity and frustration of removing data from their services. Notable examples, Intelius (and their many subsidiaries) and US Search unfortunately require a form and photo ID for information removal – the latter by fax or snail mail(!) So, while we won’t tackle these removals while we watch TV and enjoy a nice cold beverage, they are something to consider addressing with a little time and during business hours.

If you are in a sensitive situation and need a clean slate as soon as possible, I do recommend considering a paid data removal service like Abine.

 

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.