The 2020 year was not one of the best years for a variety of reasons. My personal productivity was definitely a little lower than past years, but overall satisfying enough considering what a weird and crazy year this was for everyone. Here’s what I did or did not get accomplished.

Last year I started a cloud-focused learning journey by earning my AWS Cloud Practitioner and AWS Solutions Architect Associate certifications. I completed this push by earning my AWS Security Specialty certification in May. This was an interesting experience as I tested from home as COVID-19 restrictions changed how we work and live. This was an interesting journey as I feel like my certification is slightly ahead of my practical hands-on experience within AWS. But, we have to start and proceed somewhere!

That certification would prove to be the only one I would earn on the year. I opted not to pursue another “remote” certification, plus there appeared to be no interest in having a training budget at work any longer, which meant no SANS course for this year nor any real reason to give ISC2 more money.

In the later half of the year I did take a 16 hour course hosted by Wild West Hackin’ Fest: Breaching the Cloud led by Beau Bullock of BHIS. This was an excellent course over 4 days and my only regret was not taking full days off for these. Half days kept me pretty busy! This course flowed nicely into my recent forays into bolstering my cloud experience, particularly with Azure. And the focus on the offense side gave me a different perspective than my previous defense/builder studies. I would love to go through this material again for further reinforcement and practice in 2021.

I also spent a good amount of time in Pentester Lab this year, completing out quite a few of the badges: White, Yellow, Blue, Green, Orange, Serialize, Intercept, Android, PCAP, Essential, and Unix. This was a flurry of activity and learning this summer. I made progress into other badges, but have plenty of content to get back into as I get time. Still, this was a significant outlay of time and addition to my skills and exposure to make this a highlight of my year.

I also did some online playground activities as well. I solved most of the challenges through the summer on the BHIS Cyber Range. I participating with a work team in the Splunk Boss of the SOC competition as part of the Splunk.conf conference. And I also was invited into and poked around Offensive Security’s Proving Grounds beta, which gave me a chance to stretch off some rust on my penetration testing of boxes.

Overall, that was mostly my year. It didn’t feel as productive as other years, but I’ll give it a pass considering 2020 was quite a shift and change for many reasons.

Last week, I took and passed the AWS Security Specialty certification exam. This is an advanced “specialty” certification offered by AWS centered around, surprisingly, implementing and managing security within the AWS cloud platform. This certification until recently required passing one of the Associate level exams, but today you can skip right to it if you think you can pass it. To renew, you only really have the option to take the exam again, at a reduced price.

Background and cloud path

I started my AWS cloud path about this time last year for two reasons. First, I wanted to stay current with my own skills and AWS wasn’t something I had the pleasure of supporting or playing in yet. Second, my company is in the process of moving workloads to AWS, and I wanted to keep up. In August of 2019, I passed the Cloud Practitioner. In September I passed the CCSK. And in December 2019 I passed the AWS Solutions Architect Associate. I started from Practitioner because I honestly was pretty fresh into AWS technologies and services, though not foreign to the concepts of the cloud after 18 years of IT experience. I could have tried to skip to the Security exam, but as someone painful fresh to working within AWS, I chose to do the Solutions Architect first, as many of the topics are foundational to the Security exam.

My goal has been not just to become aware of and conversant with AWS technologies, but to pave the way for hands-on pursuits, both personal and on the job. It’s been a bonus that the stars have aligned enough to allow me to learn on the job and build out a greenfield environment in AWS as we migrate into it full sail. I want to be able to understand how things are built in AWS, maintained in AWS, and secured in AWS so that I can begin to break it from the offensive side and then response to such activity efficiently. In the end, I want to be able to advise others on proper AWS security topics, both at a high level and also in the trenches.

And it’s a little self-serving; it’s a nice career safety net as well, much like my sysadmin skills and experience are to my infosec career.

Study plan

For the Security Specialty, my study plan started by learning the concepts for the prior exams. I kept a sick looking Gantt chart of my study plan efforts, but the Security specialty was definitely pretty stream-lined.

I also must mention that my original goal to pass this exam was Q1 2020. Unfortunately, COVID-19 concerns shut down testing opportunities and really stole some of my study time away, which elongated my efforts a bit. Thankfully, I don’t have other major plans for formal studying or certifications this year, so I had some personal wriggle room to push this into Q2.

As with other efforts, I started with A Cloud Guru’s course on the Security Specialty. This course is a little short on covering all the things you need, and it blasts through it quickly. And I have the same issues as I did with the Solutions Architect course where it’s just not polished, there’s plenty of mistakes that are left in the material, and it’s not nearly complete enough to rely upon to pass the exam. Still, it makes a relatively OK intro to the material. I’ll probably revisit this as review if I should renew the certificate in 3 years, since it requires taking the exam again.

My main effort centered around the related Linux Academy course by Adrian Cantrill. I really liked this course, and felt pretty darn prepared for the exam after it and after taking the Practice Exam (I scored 88% on my third and finally take of it.) This course is well over 40 hours, and does a good job being broad and deep enough to properly prepare for the exam.

Lastly, I spent time reading whitepapers, documentation, and FAQs off the AWS site on all of the security-related and core services I could. More importantly, I strongly suggest browsing the AWS security blog posts from 2017 through the end of 2019 to see scenarios and tutorials on how to do things like properly secure your root user, or incident response steps for a compromised key, or how to troubleshoot CloudWatch connectivity issues and various other common or weird scenarios. These scenarios and understanding how these work is extremely useful for the exam. As a bonus, truly read through these and follow along on the actual steps, or even recreate them in your own words.

I didn’t get a chance to use it, but if I had failed my exam attempt or started later than I did with my studying, I would have probably purchased the Practice Exam from Tutorials Dojo. My experience with Jon Bonso’s content was positive enough for the Solutions Architect that I would blindly pitch my money into this one had it come out earlier

The at home experience

I took my exam through Pearson Vue using the at home option. I thought the exam itself was stressful and difficult, but I have to say I think the at home experience was even more stressful to me. See, I live in an apartment and some of the rules of the at home component dictate a strict no sound posture. In fact, you’re not really supposed to even look away from the screen or make noise on your own! Thankfully, I have no idea what the real limits are, as I had absolutely no interruptions, noises, or contact with the proctor during my 1.5 hour exam duration. But, throughout my exam I dreaded noise in the hallway or a door shutting that would cause a disqualification!

Being in an apartment, I did quite a lot to prepare. I covered bookshelves, moved everything away from my dining table, and made an effort to minimize anything that needed scrutinizing. I had a USB web cam next to my laptop, but I was asked to move it to the top of the laptop anyway. I probably could have just used my built-in cam on the laptop. I never did hear anything from the proctor, only chat, and I have no idea if the proctor could hear me, as I typed my responses in and echoed them verbally as I did. The biggest instruction I had was to make sure a wall-mounted television in front of my was unplugged, which I had to quickly uncover the outlet and power cable to indeed show it was unplugged.

And while I apparently had no issues, it was definitely not relaxing taking the exam. Even halfway through, my head, neck, and shoulders were hurting from being all tensed up, and my eyes really yearned to just look up and afar for a bit while in thought on many of the questions. I’m pretty sure 30% of my mind was on my actions/behavior and not on the exam.

I imagine this is far, far better in a home where you can maybe go to a relatively empty basement room and keep pets/mates from making noise elsewhere, and not have to worry about much.

The exam

Basically, this exam sucks. I mean, it’s a good exam and really tests your knowledge of not just knowing how things work, but really digging deep to make sure you know or have done the steps in the many scenarios presented. I would estimate that maybe 40-50% of the questions were choose 2 or choose 3 answers. I’d guess about 70-80% were scenarios, and almost nothing was straight definitional.

Most questions were also pretty long to read and digest, and I found myself re-reading whole sections before even getting to the answers. And often the answers were lengthy as well. It was a splash of cool water when I hit short questions with short answers!

I also usually get done with an exam and I retain a litany of questions or items that tripped me up or I was happy to see, but in this case, I walked away at the end and had but one item to look up, and even then I couldn’t remember the context of the question!

Overall, I really liked the exam for what it tested against. This isn’t a light exam or something you can swing into with painfully little experience. You really have to understand how to do these things to get through it. I scored a 940 on it, and I’m extremely surprised and satisfied with that score.

That said, it should be kept in mind that this is still a multiple-choice exam. Even if a question is a big fat question mark, often one or two options will bubble up to the top and help formulate a decent guess.

What’s next?

Honestly, for AWS stuff it’s really about practical experience at work and on my own that is next. I will probably check out the Developer or Sysops Associate certs in time when I can apply those to renew the others. But otherwise, I have what I came for on the formal learning side of AWS and my immediate path to the dark side is now complete.

For cloud stuff, I’ll probably look at learning more about Azure through Linux Academy on my own time. And I’ll start focusing on topics that pertain to security and even penetration testing cloud deployments.

For security stuff, most of the rest of my 2020 was planned to be pretty informal, which works out well considering COVID-19 has changed things and put other things on hold so dramatically. I have a backlog of courses, tutorials, and other learning activities to do that would eat up years, so I want to chunk away at the juicier parts of that.

Usually when I study for a certification or course, or even for comprehension on a topic, I have steps written down to check off on my journey to that goal. I’ve probably always worked off checklists, but it feels like I rely on them more as I get older, as there’s really no excuse to not use them and forget things or lose ideas to the ether. My time really does have a personal value, and I’d like to make sure I spend it well and efficiently.

When I decided to tackle learning more about cloud security, I knew the topic involved reading and listening to materials on a topic that I’ve not been highly exposed to. And I wanted to make sure I planned out how to spend my time so that I could plan the rest of my year and have an idea when to schedule exams.

The above screenshot is a sheet I maintain on Google Sheets. In it, I basically use a Gantt chart style format to track my progression of tasks and how long they will take. I estimate the hours involved,  record the actual hours I spent, and then the remaining hours and % hours used adjust automatically. The % Complete column I update manually. For instance, I may estimate 10 hours for a task, but find it only takes me 4 hours. I can then record 4 hours and still set it to 100% complete.

Do I really care how many hours are left? Not really, but it’s a way for me to practice skills for Project Managers-Lite and be familiar with a sheet like this. Lots of things that PMs do to perform and track projects are intuitive, pragmatic things that I can use for other purposes, even if I don’t know all of the specific terms in some Body of Knowledge.

And since this is just for my own personal tracking, there’s really no grading or performance evaluation based on how accurate or well I track this; it’s really best effort and its accuracy isn’t crazy strict. It’s truly just about keeping myself on target. (And, I suppose, it reminds me what I did on my route to a certification so that I can post about it later without much recollection effort!)

I will also add that one of the more important steps in pretty much every major learning effort I tackle is researching what others have done before me. This was a huge effort in something like the OSCP where I would read reviews and thoughts and threads from others who had experienced and passed the course/exam and what they recommended for prerequisite knowledge and resources to understand prior and during the learning phases. I still do this as much as possible, and it leverages strengths I have in effectively and efficiently Googling and sifting through information and then organizing and prioritizing what I really need to do.

As a last act of 2019, I took and passed the AWS Solutions Architect Associate certification exam. The AWS SAA is the typical starting point for sysadmins and engineers looking to design, plan, and manage an organization’s presence in the AWS cloud environments. Other exams at this level are the Developer Associate for developers and SysOps Administrator Associate for a more focused dive into managing systems in AWS. (SysOp is such a great, cool term. I hope it makes a comeback over SysAdmin…) Each of those three feeds into more advanced Professional designations and also some advanced specialty designations like Security, Big Data, and Networking. None of these need to be taken in order, but they do build upon each other so it makes sense for students to progress up the chain in order.

In mid 2019 I decided to shore up a gap in my technology knowledge by diving harder into cloud concepts and security topics. I’ve spent about 17 years doing admin and security work, but I’ve not had a large chance to dabble in AWS until my current position. So, I’ve decided to upgrade myself a little bit in this regard. Since then, I’ve earned my AWS CCP and my CCSK designations. I decided to remain aggressive and hoped to get this AWS SAA before 2019 ended.

My goal with this track of study is really to study for and take the AWS Security Specialty certification exam, since…well…I’m a security geek! The CCSP is also on the roadmap, but mostly for its recognition and the fact it won’t really cost me anything additional to keep renewed along with my CISSP.

For study, I really kept to the same blueprint I use for most certifications. I start out by researching the exam, the exam topics, and what other successful students have reported and reviewed over the most recent years. Often, I do this by searching the TechExams forum, reddit, and then also Google. I write down various ideas and resources those students used, research those sources, and start to formulate a plan of attack. Sometimes, I’ll solicit some advice from some peers on Twitter, Reddit, or other media, but often I usually self-research.

I opened up with a 7-day free trial to A Cloud.Guru and blitzed through their AWS SAA 2019 offering as quickly as possible. At 12 hours, this wasn’t too bad. But, also at “only” 12 hours compared to the Linux Academy course at 54 hours(!), I assumed ACG’s offering wasn’t really going to get detailed enough to rely solely upon. Overall, this course at ACG makes a good intro, but the presentation quality and style definitely go up and down. Some sections of the course are recorded with lower quality equipment, which means section to section you can experience very different sound levels. This becomes pretty distracting, even annoying. Likewise, an editor must not have been hired, as there are pauses and even retakes within the audio that are still present. Overall, I felt I could trust the author, but I also somewhat felt like the author rushed to get this out and it’s just not that polished. The material, however, was solid. I did not do any labs on ACG. I did like the meaty quizzes at the end of each section, though the grammar on them is spotty and the reasons for the answers are at times woefully brief, sometimes just repeating the actual answer rather than a reasoning for it

Later on about a week before my exam, I would open another 7-day free trial at ACG just to consume their Exam Simulator, which is just a practice exam whose questions are pulled from some pool of questions. I ran through this twice, and only had maybe 1-3 repeat questions out of the 65 given. That said, the grammar on these questions was outright terrible, and I honestly felt dirty for going through the experience. Still, plenty of questions reflected the sorts of topics and questions I saw on the exam.

I then spent the bulk of my study time on the 54-hour beast of a course, the AWS Certified Solutions Architect – Associate Level (id=341) by Adrian Cantrill and hosted on Linux Academy. This course includes LA-hosted labs which performed very well for me and a supplement, The Orion Papers, hosted on LucidChart. I was initially very lukewarm on the LucidChart materials, but by the end of my study, I was actually referencing them regularly for refreshing and reviewing various topics. The course itself is excellent with a high quality of delivery throughout. I did not like the quizzes nearly as much, but they do reflect the material presented.

I took the practice exam at the end of this course, and also an older LA-based practice exam from the 2018 course. I didn’t like either of these practice exams as they seemed overly specific on various bits of knowledge that go beyond what you are expected to know for the Associate level, like calculating RCU/WCUs. I found both quizzes to be strangely pulling from the same pool of questions (or at least written by the same people and/or borrowing from each other), and overall found it frustrating.

About halfway through the Cantrill course, I signed up for a package of 6 practice exams hosted on Udemy by Jon Bonso (TutorialsDojo). I really liked this set of exams and found them to be challenging at just the right level, both while I was still completing my studying, but also in retrospect after passing my exam and thinking back to where overlaps occurred between the exam and these practice materials. I initially was scoring below 70%, but as I finished up the core of my studying, I was pretty consistently getting 75% on my first attempts on those exams, and 85% on subsequent tries. I reviewed all questions after each attempt, making mental note of reasons for questions I got right, and physically writing down notes on questions I got wrong (or just guessed on). I would then re-attempt one of the practice exams after a week or more. Even if you pay full price for those (which I think is $40), this set of practice exams is definitely worth it.

Despite plans to do so, I never really consulting the official AWS whitepapers, FAQs, or Best Practices for the various services. I would sometimes get into them very briefly when Googling answers/reasons for practice exam questions, but never sat down to comprehensively go over them. I also briefly looked at the TutorialsDojo cheatsheets, but I had expected really quick cheatsheets and charts and diagrams, but instead they were pretty lengthy, so I didn’t really consume them.

I also never really went into depth on my own AWS account or fired up any projects of any merit. I would still say 80% of my AWS hands-on experience before my exam was fueled by the Linux Academy labs. That said, my extensive general IT experience hosting critical web sites helped me with many troubleshooting questions and understanding some difficult concepts like using load balancers, traffic encryption, and network layouts. Someone with less IT experience should probably expect to do a little more hands-on work in AWS to prepare for the SAA exam.

Overall, I somewhat casually studied from mid-September until the end of December en route to my exam date. For other students, I’d highly recommend going through the route I did: ACG course, LA course (Cantrill), and then Udemy practice exams. I’d then suggest looking at the AWS Whitepapers, FAQs, and Best Practices to finish up. If you already know about how AWS works, concepts on why cloud makes sense, how AWS bills you, how AWS support plans are structured, and the general one-line definition of the most common AWS services, I think AWS SAA is the place to start. Lacking that knowledge, first taking the AWS Certified Cloud Practitioner is a great stepping stone into AWS knowledge.

The exam experience wasn’t really out of the ordinary. I scheduled my exam during winter break at the college I usually take exams at, so the whole atmosphere was casual, chill, and pretty dead overall. I spent a full hour on the exam, and that even includes flagging questions and reviewing the first 20 questions over again. I did not feel entirely confident in my attempt after the first 12 questions, but they seemed to ease up in the latter portions. I normally do not review or go back to previous questions in exams, but I did do so quite a bit in this one. Still, I don’t think I changed many answers at all. It is possible to go back and review every question whether you flagged it or not, which is nice. Passing means achieving a score of 720 (possible 100-1000), and I scored 836 for a comfortable pass.

Overall, I think the AWS SAA is a good certification to ensure that someone who does already or wants to start working within AWS to design solutions and troubleshoot issues is prepared for that task. That said, I have next to no practical experience in AWS (that’ll change!) and was able to pass, so I would say this exam is appropriate for people with 0-2 years of experience with AWS services. That also means possession of this cert may not attest to someone’s actual expertise in AWS, but definitely attests to having a grasp of the fundamentals enough to not be a clueless disaster. (And honestly, that can even be said about the CCNA or any other technical cert.) Despite that, I actually feel far more conversant and novice-level competent in understanding and doing things in AWS, especially in comparison to my pre-study state. I’m hoping future projects will fill in further gaps.

As intimated earlier, the AWS SAA is a stepping stone towards my real goal of achieving the AWS Security Specialty certification, so that will be my next step on this journey. I also have the ISC2 CCSP on my radar, but I think I’ll keep with the AWS focus for now, and plug in the CCSP later. Since the CCSP is more theoretical than hands-on technical, I am skeptical what I’ll actually learn from the CCSP, but I may end up surprised!

Years ago, I became aware of the book The Phoenix Project (Kim, Behr, Spafford) and added it to my wishlist, but never actually picked it up. I remedied that issue over the past couple weeks by picking it up on Kindle and going through it. Rather than post a reaction or my thoughts on the book (at least for now), I just wanted to tell a small personal story that this book made me think about again.

Back around 2007, I worked as a sysadmin, and one of my main duties was supporting the servers hosting our critical web sites that developers developed. Thankfully we were already well into the virtualization takeover, but we were still using Microsoft’s Network Load Balancer tool to spread load across about 7 Windows Server 2003/IIS 6 web servers in one data center (the outfitted closet behind my desk). These sites ran .NET code using all sorts of virtual directories and COM objects tucked into corners of the server. And other things which I’ve thankfully lost memory of!

We had dev, test, and production environments, if I recall correctly. Deployments to dev and test took place Tuesday and Thursday afternoons, and would take several hours of manual work and testing to perform, during which time that entire environment was inaccessible to anyone due to the things needed to be done to support installations and configurations of IIS and COM. Part of the COM install was done by a homegrown tool built by someone I didn’t know and no longer supportable, but the rest was manual labor. And if one team needed a deployment, every other team pretty much had to feel that outage with the shared resources.

When I took this over, I immediately started doing a few things that seemed natural to me. I first made a clear checklist to follow for each deployment (know your work!), thereby removing the need to remember each step. I then started automating the pieces I knew how to automate using batch scripts to move files around.

At this same time, my company was also performing the implementation stages of a company-wide DR/BCP project. We added a second data center and my server farm was about to grow from 7 production web servers and about 4 dev and test servers into about 50 and more. We were also plugging in dedicated hardware load balancers as a much needed upgrade to NLB. And we then needed to solve file replication challenges when supporting two data centers that needed to fail over each other. Exciting times!

But this expansion meant I needed a new solution for deployments. Devops was still not really a thing. PowerShell had just recently come out, and I decided to try learning it in support of this coming build-out. I mean, no one wants to work for hours and hours just doing tasks that a monkey could do on servers.

So I created a PowerShell script that would perform these deployments automatically. My script would run on every production web server perpetually. They would all “check in” to a common configuration file and would “elect” a master who would do the controlling of another installation configuration file. When I needed something configured, my script would orchestrate the installation kick-offs with each other server in a predefined sequence. When a server received a command to do an install, the script would delete everything in IIS and remove all the other things, and then build them all back in every time. I had around 100 sites on these servers, and it was pretty glorious to see them all run through these installs for a few hours. I minimized downtime when possible (you know, database changes making this not possible) by utilizing the load balancer to know when a server shouldn’t have traffic, and when it was good to have traffic again. This was all replicated to separated (and expanded) dev and test environments as well as the servers on the DR site. Flipping over to a DR test was really just a matter of changing DNS and waiting a bit while the database then also failed over (pre-Availability Group days).

I solved quite a few problems with this setup. I lowered the amount of time an admin needed to spend doing deployments. I also lowered the amount of time overall for deployments. Deployments could be scheduled and run unattended at any time (weekends, nights). Outage windows were greatly reduced when they were even necessary. Most of the time, by orchestrating traffic direction by the load balancer, I could allow devs to do seamless deployments any time they wanted. I could scale this up (to an extent) to accommodate our expanded environments. I was able to achieve server consistency by not only removing human hands from the deployments, but because I rebuilt every IIS server, I eliminated those inconsistencies admins introduce when troubleshooting something, getting interrupted, and never getting back to set things back to how they should be. With a few networking exceptions, my dev environment was also comparable to the production environment, so if a developer could get their code to run in dev early in the dev cycle, it would also run in prod (none of this, “it works on my laptop!” crap). As a side benefit, no one could add something to the server that wasn’t part of the known build procedure, as the script would wipe it out or just not know to include it. And the script and its configuration file were self-documenting for what was needed.

Things were good, but they got better as time went on. When we migrated to Windows Server 2008 and IIS 7, I completely rewrote the script. I removed the need to pass a “master” token around and decoupled the script from the servers. I ran it on a dedicated system and utilized remote sessions to make changes on the servers. I also decoupled the actual copying of web code from my scripts and better utilized DFSR. This allowed developers to make simpler file changes within seconds if they wanted to. This also pushed management of “dev first, then test, then prod” pipelines to development hands, taking me out of that decision structure. I also made sure my script could install pieces and parts of sites rather than the whole server, if desired (will still keeping the ability to do a full clean and install). When moving to Windows Server 2012 and IIS 8, I again made smaller changes to improve support.

By the time I was done with the last iteration of my scripts, it was about 2013 and we ran that infrastructure until I left in 2016. We didn’t really dive too hard into devops, since we didn’t really have to. I had somewhat naturally found those concepts by improving delivery, improving consistency, reducing risk, and reducing my pain felt during deployments and in support of mistakes. No one should like to be forced into constant heroic efforts to keep the lights on.

Many of those lessons are buried in The Phoenix Project, which is really the same story of an IT shop in a (rather busy) company also discovering how devops improves IT operations. It doesn’t take an Erik oracle or threats of a business falling over to figure out how to improve operations or fancy production floor studies and terms to understand how to ease your pain and make things better. If you allow it, it should happen (to a degree) on its own as people manage their little fiefdoms more efficiently and reduce their own personal pain.

Had I remained with that company, I’m pretty sure I’d have next dumped my homegrown PowerShell scripts and done one of two things: Either continue with my fiefdom and implement more situated devops tooling like Ansible to manage the environment, or marry up to developers and their chosen packaging and deployment pipeline (their issue being they couldn’t get every team to decide upon just one).

The Phoenix Project has many more nuances; it’s like taking the IT issues of 50 companies over 5 years each and compacting them all down into one year of just one company. It’s a little silly, but it illustrates all the pain that eventually led many teams and engineers down the general path of devops. Which is still really just about keeping things in line with the whole utter point of IT: automation.

(This is an incomplete draft I’ve had for a while now. I don’t think I’ll ever complete it, but I didn’t want to lose it or keep it as a draft, so here it is.)

Daniel Miessler has a great article up: “If You’re Not Doing Continuous Asset Management You’re Not Doing Security.” You honestly cannot dislike that title, and the article itself is full of the points enlightened security folk should already have in their heads.

There’s a reason the top 2 controls in the CIS Top 20 Critical Security Controls are all about inventory. It drives every other thing you do in security, and without it, you’re managing by belief and never really sure if you’re being effective or not.

There are many different ways to tackle inventory, but here are some of the common ones:

• workstation-class devices – This is usually one of the easiest to handle, since the team responsible for workstation procurement likely has an inventory of what they have in order to please customers. Being able to tap into this inventory list, or at the very least view it, is essential. For instance, how do you know you have Antivirus or endpoint protection on every workstation? You have to true that up with the inventory list. Think about the question, “How would I know something is missing security control XYZ?”
• mobile devices (on your network and/or company-owned) –
• servers – Typically, one team manages workstations and another team manages the servers. This team should have a handle on some beginnings of an inventory system due to licensing needs, storage/compute resource needs, and other OS-specific collections such as Active Directory or patching coverage. But the same question applies herre, “How would I know something got missed in inventory?” Or in the case of a largely Windows environment, “How do I find a new non-Windows assets that is stood up without notice?”
• networking assets – This could include diagrams of the networks, both logical and physical when needed, for both wireless and wired networks. If the networking team manages it, it should be in this group.
• all other network devices – This covers all the other things not nicely slotted into the above categories, like appliances or IOT. This also covers unauthorized device discovery. Essentially, if something is on the network, it needs to be found and known.
• the cloud – The cloud is often a different beast, especially when consumed dynamically with assets coming on and off as demand moves. Worst case, you go through all other steps above over again with “cloud” in the front of it.
• internal information systems/sites – This is about knowing the information systems that your business and users consume, which often comes in the form of internal websites, but could be other tools and systems. Largely this is defined by things that store/handle data.
• software and applications – A huge endeavor on its own, but nonetheless important to know the software and applications in use and needed (and hopefully approved and tracked).
• external attack surface/footprint – This is what attacks can see and will target; high risk and high priority assets and paths into the organization. This isn’t just Internet-borne, either, but could come in through other weak links such as wireless networks or VPN tunnels.
• vendors – A good risk management program will have an inventory of all official vendors, which will fuel risk reviews and inform security of what is normal.
• third-party services hosted elsewhere – What services does the business and its users consume that you don’t strongly control? This likely will still impact account management and permissions, data tracking, and evaluation of those services since you have some measure of intrinsic trust in them which is a potential risk for you.
• critical business systems – This could be considered a little advanced, but it’s about knowing what’s really important to the business, which informs risk priorities, spending, and other activities like BCP/DR.
• data/critical data – You can’t secure data if you don’t know where it is, and have some idea on what data is more important than others. Yes, this one is difficult outside of narrow compliance definitions (aka all data vs just credit card data). Honestly, this bullet item should be a top level category in itself.
• authentication stores – This is about knowing what accounts you have, where they authenticate against (are stored), and what your users and systems actually use to do things.

There are different methods to find this out:

• process/documenting – This is the default method shops will use to track inventory. If someone stands up a new box on the network, they update some inventory sheet or make sure they follow some checklist to include the new asset in something else (adding it to monitoring, patching, or joining a domain). This is a trust exercise, as you need to trust that every team member follows the process and every process is all-encompassing. This includes decommissioning assets as well. This should also include the assignment of ownership: who in the company is ultimately responsible for this asset?.
• active/finding – Most of the time, security should assume the worst (trust, but verify), which would be finding assets that are weird exceptions or just get missed in the normal process. Active inventorying means looking out onto the network and scanning it, finding assets, identifying them, and pulling them back into visibility/compliance. The opposite is true as well, you want to find assets that aren’t meant to be there!
• passive/watching – There are also passive techniques to find devices, such as watching all network traffic or alerting (and even blocking) unauthorized assets from accessing the network. This is still a fallible control, but it is part of the puzzle of knowing what is on a network.

There are a few caveats to the above. First, it’s not 100%; there may be a “bump-in-the-wire” or other passive device on the network (think a network tap just collecting data). There are also device peripherals (mice, keyboards, headsets, readers of various types…) Tackling this is a bit advanced. Second, especially with the active methods, this needs to be done continuously, or the controls need to be continuously active. If you do active scans once a day, an attacker or insider could still turn on a device, do whatever, and turn it off in time for the next scan. Handling these windows is why we practice continuous improvement and defense in depth and why we map out maturity plans.

And Miessler includes 5 questions that drive the measurement of a security teams based on how they answer them:

1. What’s currently facing the Internet?
2. How many total systems do you have?
3. Where is your data?
4. How many vendors do you have?
5. Which vendors have what kind of your data?

(publishing an old “incomplete thoughts” draft) We all have a preferred environment and/or music we prefer to hack and learn and work in. Most recently, I spent much time at home practicing and learning in the PWK/OSCP labs and exam, and often to a background of music. I thought I would share some of my interests in this regard. If you read nothing else here, at least go give SomaFM a listen, particularly their DefCon Hacker Radio and Groove Salad stations. I’ve been a regular listener of Groove Salad since around 2003, and it’s absolutely excellent.

When I’m heads-down doing something, most of the time I’m probably listening to one of four types of music.

The most common for me is “chill out” music, largely electronic, but could also be acoustic or traditional. This largely stems from enjoying new age music from the 80s/90s, which then expended into electronic music through the late 90s and on (think Enigma and Kitaro transitioning into Underworld and Sasha). Unless I’m listening to my own stuff, this is where I’ll tune into Groove Salad on SomaFM. I don’t remember how I found the station or why or what led me there, but it definitely solidified “chill out” as a thing that I totally dig. (And I totally geeked out when BackTrack used to include a SomaFM bookmark in their default browser!)

I’ll also enjoy other electronic music, but if it has more intensity or a beat to it, I don’t include it into the chill category, and instead gets lumped all together into my general electronic folder. This encompasses anything from classic trance, goa/psytrance, dubstep, edm, and so on. I tend to stick to my own collection when listening to this, but might queue up a large set of stuff on YouTube, or use SoundCloud to listen to some sets or DJs, or maybe Pandora, or Digitally Imported feeds on TuneIn Radio.

Sometimes, I’m in a really heads-down mood or just want something less electronic, and I’ll turn to either normal classical music, or something less orchestral like cello, guitar, or piano artists doing their own thing. Most of the time when I listen to this, I’m firing up TuneIn Radio and just listening to the Iowa Public Radio Classical station. No ads, decent quality, good variety. Failing that, there’s tons of long collections on YouTube to listen to.

Lastly, I’ve also always enjoyed hard rock which borders into metal, but never really metal. I tend to be pretty picky when it comes to this (Metallica, Tool, White Zombie which betrays my age…), but more lately I’ve gotten into symphonic metal bands. I still have plenty of things I consider to be “harder” rock music (basically anything more intense than “pop” music), and sometimes that’s my mood.

A while back I earned my OSCP. I have written my reviews of it in two parts, once just on the logistics of my course experience, and another with advice to others. I often see requests on what to do to prepare for the OSCP or what it takes to earn it, and I have a saved response that I often give out to those learners. And I realized I’ve never really put it down here on my blog in complete format (a large chunk of it comes from the aforementioned advice post). So, here it is in entirety: my advice to people with the question, “Am I ready for the OSCP?” (A.K.A., part 3 of my OSCP series…)

Let’s first take a step back and ask this question: “What do you hope to get out of the OSCP experience?” In other words, “What is your purpose?”   

There are two main goals for the OSCP, though one really overshadows the other. First, the OSCP cert will open doors to pen testing and other security jobs; it’s a way to confer some immediate credibility amongst those who know what the cert is about. Secondly, and most importantly, the cert and lab are ways to teach pen testing methodology and frame of mind; how attackers work. It’s not about pwning more systems, or getting another add on the resume/CV; it’s about learning how to think like an attacker and efficiently evaluate systems and provide value for customers and admins.  

My OSCP prep advice is pretty much always the same, and yet it depends on what every student brings to the table. For me, if I were making an OSCP cocktail: 

• 1 part Windows admin – know how to turn services on and off, add users, change passwords, browse through cmd and windows explorer, RDP, etc.
• 1 part Linux experience – Know how to move around directories, read files, create files, use a text editor, create users, change passwords (linux essentials or linux+ prep courses will help)
• 1 part LAN networking – TCP/IP knowledge, ports, arp, wireshark/tcpdump familiarity, firewalls (host and network), dns
• 1 part security knowledge – general attack classes, goals, major OS vulns over the past 20 years; a pen test course or book works
• 1/2 part Kali experience – poke around it a bit, experience installing it, logging in, location of some tools and the interface
• 1/2 part Metasploit knowledge – have used it a bit, run through the free Metasploit Unleashed course
• 1/2 part web server/client knowledge – nice to have hosted anything with apache/iis in the past and understand config files, ports, php/javascript a little, client vs server-side processing, dash of SQL syntax
• 1 part coding/scripting logic/basics – if you can make a bash/perl/powershell/c/python script or have coded in the past enough to read and minorly edit script/code chunks, you should be good to start; nothing amazing
• Sprinkle of efficient Google searching ability 

Bring all of that or more to the table, and you’re set to be slammed in the face with the course material and then hit the ground running in the labs.  

Keep in mind, the course is an entry into pen testing; it’s not a requirement to have popped root shells in the past. The course will grab your hand and start you off the on the path. 

If you want the best example of what you’re in for, go to cybrary and have a perusal at Georgia Weidman’s Advanced Penetration Testing course. It’s free, and will be the closest and quickest way to see what you’re in for. Vulnhubs and hackthebox are fine for practice and to understand the process of enumeration, but they’re not necessary at all. 

Google for OSCP reviews. They are full of suggestions and resources, and usually give a great idea of what the course and exam experiences will be. Don’t over-mystify the course or exam, and thus, don’t over-prepare! Dive in and get on it. 

Try to become familiar with the Kali Linux and the tools it has and the layout. This will be your home base for the course, and has pretty much everything you’ll need.

For those newer to Linux, start using a distro on a day-to-day system and find some online courses on Linux security and administration and shell scripting/commands. Linux+/LPIC-1 level skills are good, anything beyond is great. Also suggest a Bash Shell/Scripting primer.

For those newer to Windows, find some courses on Windows security and OS administration. This includes hosting server-type applications (e.g. web platforms).

Learn some Metasploit. It’s worth it and it’ll get used, whether in the course or beyond as a pen tester. Off Sec has a free Metasploit Unleashed course.

Learn some basic, free, staple tools and get comfortable with working various switches: nmap, unicornscan, curl. Google the top 100 security tools and at least know what you could use each one for. You don’t need to wield/install each one, but feel free to try any out.

To get familiar with some of the big security issues over the past 15 years, grab a copy of Hacking Exposed (McClure, Scambray, Kurtz).

For pen testing theory, check Penetration Testing: A Hands-On Introduction to Hacking (Weidman) or the slightly more up-to-date The Hacker’s Playbook 2 (Kim). The Hacker’s Playbook 3 is even more updated!

Have a decent enough grasp of networking to know how TCP/IP works in general, use and read some Wireshark/tcpdump output, and understand IP addressing, firewalls, and ports.

Have a decent grasp of how web technology works, from configuring web servers, looking at simple HTML/PHP/ASP code, simple SQL queries, and how browsers interact with the web server.

Install some security-related browser add-ons and poke around the Developer tools in place in every major browser these days (F12).

Dive into Python or Perl enough to get into Socket or web request programming. Very useful to start swimming in the ocean of editing or making exploit code or enumeration scripts. Having had a course or class in basic programming is great, as you can start to consume any language if you know the logic. (This is not necessary, but very nice!)

Start thinking like an attacker. This often comes with experience, but start thinking of ways you can get to Goal X or Access Y. What mistakes do you look for? What isn’t default?

Lastly, know that OSCP/PWK comes with course materials and videos that teach you everything you need. So don’t think you are going into this being tested from day 1 and spend 2 years trying to prepare for something that is meant to teach you new skills in the first place. You’re going to be learning from day 1 until day X.

So, what can you do to practice, if that’s what you feel you need to do? Download and install a Kali VM. Join Hackthebox (HTB). Watch Ippsec YouTube videos on retired HTB boxes and follow along. Download VMs from vulnhub and follow walkthrus on those boxes. Read OSCP reviews for more viewpoints. Pwn and have fun!