April 21, 2019

From Grey to White - An Unspoken Ethical Journey in Cyber Security


I write this blog entry at the risk of tarnishing my personal and professional reputation.  I do so in hopes that it will help others who are starting out in this industry or those who are still in the grey zone know that this is likely a familiar path for a lot of us "professionals" in this space.  We don't speak of it, often times because of the ethical oaths we've taken in order to obtain our professional certifications or positions in law enforcement, etc.  It's also something I think we've put behind us, even though it's an important part of who we are.  Even though a Black Hat is something I never have considered, I'd be lying if I said I was always the White Hat I am today.  One of the pillars of these professional certifications is "Truth" and "Honesty", so pretending my past was always without blemish and perfectly ethical would be a direct violation of this.  

I want to tell my story because it's part of who I am, and I hope it encourages others who may be in this area of their lives to know that many of us (now) White Hats started out in much the same way.  Many of us have turned a passion into a career that is rewarding, but if we're honest with ourselves, we're still "hackers" at heart.

UPDATE : Ironically, as I finished writing this, current events around Marcus "MalwareTech" Hutchins have stirred a debate in the Cyber Security community on this very topic.

My Story

circa 1993

The year was 1993 and I was in entering the 4th grade.  Our 14 person elementary class (93 in the entire school) was lucky enough to receive a grant allowing us to take home our very own personal computers.  Mine was an original Macintosh (old by then), which I quickly became obsessed with.  We eventually upgraded to newer models.  All of the students along with their families met after school one evening and we were taught how to plug everything in so we knew what to do when we got home.  We also had external dial-up modems we could use for faxing and "electronic mail".  I took it upon myself to remember every cord and every physical component on the machine.  I think I took some pride in knowing just as much as the adults in the room at the time, since we were all new to this.  I can thank this very moment for what set everything in motion for my career today, that same drive and passion fuels me even now.

"Former Indiana School Superintendent H. Dean Evans helped formulate the Buddy project during his eight-year tenure that began in 1985.  Evans said his original hope was to have a computer in the home of every child from kindergarten through high school.  He sees a time when elementary school children will use computers as spontaneously as they now use pencils and crayons."  Thanks, Mr Evans!  We'll throw modern phones in as computers too and.. what are pencils?


Fast forward to 1996.  The movie, "Hackers" just came out within the last year, but I won't end up watching it for another decade or so.  I'm eleven years old and I love my Mac but felt like I had done just about everything I could imagine on the thing.  I was itching for more.  My dad was awesome enough to recognize my drive and had the foresight for the technology boom in the future so he bought the family a Compaq Presario PC with Windows 95 and America Online on it.  Don't forget about Encarta!  Now we were cooking with gas!

Our $2,500-ish 233Mhz PC

Needless to say, for the next few years I became completely obsessed with this machine and everything it had to offer.  I was "viewing source" on websites I admired and memorizing HTML to build my own web pages.  Like everyone else at the time I was heads down in IRC and AOL Instant Messenger (AIM) and I was playing video games like Duke Nukem 3D, Doom, Flight Simulator 95, Jedi Knight Dark Forces, and others.  I learned how to create "hacks" for Jedi Knight DF2 and would have fun playing multiplayer games with those advantages.  I created a player editor for that game as well in Visual Basic.  As I started to program I enjoyed making my own RPG games and I was just getting into building my own computers from extra parts.  Search engines were pretty terrible at this point so I was self taught, mostly because I would break the computer every-possible-way and would be afraid of getting in trouble by my dad so I'd have to fix it.  I did end up making my own meta-search engine to combine results from the greats (AltaVista, Ask Jeeves, Lycos, Yahoo, etc).  This was back when results were less about reliability and more about quantity.

I learned a lot about file systems, registry settings, partitions, how to format and restore an OS, drivers, you name it.  It's embarrassing to admit now but I used to lay awake at night staring at the LEDs on my desktop and hoping I could absorb some of it's knowledge, through osmosis or something.. I would fantasize about being on a competitive panel of "experts" one day and being able to answer every computer question that was thrown out.  Other kids were being eleven-year-olds.  

I'll try to move along, my nostalgia isn't going to rub off on all of you readers who are surely getting bored by now unless you can relate to this time.  I know many got started much earlier or even later in their careers, so let's jump forward to 1998 when "Security" became my new obsession.


A little backstory, I grew up in a small farm town where most other peers were into agriculture and I was the lone one into technology.  I actually somehow managed to get an "F" (my only F in HS) in Agriculture class.  As people started to get into computers around me, our small town would often call and pay me to "fix" their computer problems as I developed a reputation as the local help desk kid.  As a thirteen year old I pretty much knew the ins and outs of Windows 95 and now Windows 98.  Looking back, it seemed everything was a driver or hardware issue!  I spent most of my days on the computer, so much so that I'd often forget to eat meals and my parents would eventually "ground" me from the computer so I would be forced to leave the house and socialize with other kids.  Again, shout out to my parents or I may have wound up so introverted I couldn't communicate like I can today with both technical and non-technical peers.  

One day my dad was talking about this annoying new policy at work where if he doesn't move his mouse for a while the screen will "require him to log in again".  I realized this was a lockout policy and was for security reasons, but I was determined to help get him around this.  Windows 98 at the time had something called Active Desktop, which essentially were HTML web pages that could be used as a desktop wallpaper background.  I had an idea to create an iframe or JavaScript or something that would refresh on a certain interval to make it look as if the computer was actively in use, preventing the lockout from occurring.  My dad thought this was the greatest, but ironically it goes against the very advice I give now a security consultant.

Anyways, the real reason we're visiting 1998.. crashme.com is now a thing, and I heard about it from other kids in my Jr High school who had computers.  There was a pretty small group of us and we were super nerdy, as you can imagine.  This was a site which contained some Windows 95 and Windows 98 Denial of Service (DoS) vulnerabilities that would crash the OS, regardless of which browser you were using (choose between Netscape Navigator or Internet Explorer, yay!).  When I say "crash", I meant your PC instantly got the infamous "Blue Screen of Death" or BSOD by simply visiting the site, and the only way around it was to flick the I/O button and physically turn off your PC.  

As soon as my speedy 28.8kbps modem rendered the site, my face lit up with awe and excitement when my new blue wallpaper greeted me.  How in the world was this working?!  How can I bottle this up and re-use it?  I can't "view source" because by the time I get to the site my PC will crash.  I had an idea, I'd grab the contents of the site from my "Temporary Internet Files" directory which cached the contents of the site locally.  Success!  I could now see what the code was trying to do.  This exploit was pre-Common Vulnerabilities and Exposures (CVE), so it was simply known as the c:/con/con or "con con" vulnerability.  

crashme.com code, thanks to the way back machine!

For those that aren't familiar, Ars Technica describes it well.  "The Windows 9x-era bug was due to an error in the way that operating systems handled special filenames. Windows has a number of filenames that are "special" because they don't correspond to any actual file; instead, they represent hardware devices. These special filenames can be accessed from any location in the file system, even though they don't exist on-disk.

While any of these special filenames would have worked, the most common one used to crash old Windows machines was con, a special filename that represents the physical console: the keyboard (for input) and the screen (for output). Windows correctly handled simple attempts to access the con device, but a filename included two references to the special device—for example, c:\con\con—then Windows would crash. If that file was referenced from a webpage, for example, by trying to load an image from file:///c:/con/con then the machine would crash whenever the malicious page was accessed."

Remember too, this was 1998 and people didn't patch Windows like they do (or don't do) today, so almost everyone was vulnerable for several years.  It's about this time in my life I enter the fitting room known as my bedroom and try on the super alluring grey hat.


Around this time my best friend was really into a virtual chat environment who, you guessed it, was one of my computer buddies in Junior High.  He played this thing all the time and took it super seriously.  You know, like how people are into World of Warcraft.  Is that what kids are into nowadays?  Did I mention I'm old?  Anyway, he talked me into joining and I realized there were tons of people on this thing and it allowed for unfiltered HTML in the public and private chat rooms.  I think you know where this is going..

I realized I could "weaponize" this code with a simple image tag in a chat room and I'd see people drop like flies from the channels.  I could also DM people directly and target them to crash.  I got a super sick rush from this and thought it was pretty much the coolest thing in the universe at the time.  I didn't think about how I was potentially making people lose their saved work, but I thought it was pretty harmless since it shouldn't damage any equipment.

This led me down another path, since I realized HTML could be rendered in direct messages.  I thought, "Well what happens if I create some JavaScript that causes a recipient to make a call to a resource I don't have access to?"  For example, could I send a message to someone which then causes them to message someone else?  This was a beginning of an obsession of mine dealing with Cross-Site Scripting (XSS) and Cross Site Request Forgery (CSRF) before I knew they had names.  I realized through trial and error that for another URL to be called successfully, it had to be URL encoded, but I didn't know what this was at the time.  I just knew certain characters wouldn't work in my payload unless they were "converted" (encoded) to a hex equivalent.  I ended up making my own URL Encoder tool and pretty soon I was terrorizing the virtual town.  

I created payloads that would use CSRF against privileged moderators in the channels and the payload would cause them to delete other user's virtual houses or give me virtual currency in the game.  One of my attacks I tested against my good friend which was designed to message an Operator from his account, which then cursed them out and taunted them to ban him.  I thought this was so cool and couldn't wait to hear from my friend if it worked, my only way to verify the attack, until he called me up and was understandably upset.  I had forgotten how important this was to him and I just got him banned for life under his account.  He rightfully didn't talk to me for a month or so afterwards.  Let this be lesson one for me going down the "dark side" of Information Security.  It wasn't as cool for the victims as I thought it was for me at the time.

I then decided to get out of CyberTown and give up being a nuisance.  I friended a stranger in a chat and told him about my "abilities" which he was very interested in.  I shared my payloads with him (another bad idea) and went on my way.  I later saw in the news (from CyberTown's own site) that someone was going to be prosecuted for "hacking" CyberTown and based on the description of the attacks, couldn't help but wonder if it was the same guy.  A close call?  I remember times when the doorbell would ring and I'd be afraid the FBI was at the door, no joke.

Trouble at School #1

Back in the day, emails with embedded HTML just rendered fully in the client by default.  As a time reference in history about now, the ILOVEYOU worm is all over the media.  I'm now a freshmen in High School and we had our very own network administrator.  She was a kind lady, but I saw her as a technical opponent at the time for whatever reason.  I guess being a teenager I was just stupid and thought I needed to demonstrate just how much smarter I thought I was than her.  I was known as one of the "nice kids" who never saw the principals office and never got into trouble or created attention for myself.  I had the ill-conceived idea to generate an email that just simply showed a green smiley face I created with an embedded wav file maniacally laughing (something to the tune of "MWUAHAHAHAHA..").  I figured the last thing she would see was this before her computer blue-screened.

Being young and dumb, I crafted the email and modified my "sender" address to something made up so I wouldn't be recognized.  I looked it over and without a second though and only a smile, I sent it on.  I got that same rush after it sent.. I knew when she opened it her computer would crash and she wouldn't know who sent it.

The next day I'm sitting in a humanities class when all of a sudden our lesson is interrupted by an office assistant.  She's holding a pink slip in her hand and my stomach suddenly felt queasy.  I knew at that moment she was there for me, and, sure enough she was.  As she announced my name, it's like every head in the class turned to look directly at me and I heard people whispering, "What did he do?".  

As I'm walking to the office all I can think about is how they caught me.  Were her skills superior to mine?  Did she have some advanced way of tracking down the origins of my image or email in some way?  Instead of feeling bad about the attack, I was focused on the technical.

The reality of the situation hit when I entered the office and I saw the disappointed facial expression of the network administrator, the victim of my attack.  I instantly felt awful seeing a person on the other end of this instead of a recipient address.  Like my friend, I got the impression it wasn't just a "cool prank" to her either.  We went in her office, and she was unbelievably gracious to me.  She asked me why I did it and I didn't have a good answer for her.  I told her I liked her.  She was nice enough to tell me to keep my voice down so the principal didn't her us, she was trying to protect me!  She said something like, "Look, I know you can probably do circles around me on a computer but you should put your skills to good use instead of bad.  Also, my computer froze when I opened your email and I was afraid to turn it off so it laughed loudly all night.  My husband and I didn't get any sleep.  Do I have a virus?".  To which I replied, "Oh no nothing like that.  It's just a harmless prank that causes you to force shut off your computer.  No damage should have been done to your files and I didn't expect it to laugh like that on an endless loop.. so...sorry about that!  Oh, by the way, how did you know it was me?".

She explained that my full name was simply at the bottom of the body in the email.  Are you kidding me?!?  I should have known that the email client I was using auto-inserted a signature with my fully registered name (silly me) so even though I had taken the time to mask my sender address it was all for nothing.  DOH!  Let this be lesson two!

Trouble at School #2

I think I'm a Junior in high school at this point.  I've poked around at home on my Internet connection and discovered a POP mail server hosted by my school.  Because the email naming convention was simple, I generated a quick list of all teacher's email addresses.  I didn't have their passwords, but I figured I could bruteforce them over a POP3 connection quickly enough.  I used a tool called Brutus (et tu brute) that would do exactly this for me against a wordlist of user accounts.  I fired it up one night and went to bed.  When I woke up, I was shocked to see it had successfully cracked about 90% of the passwords!  I didn't expect this, but soon saw that a majority of the credentials were the original default of "hawks".  Our mascot was "The Blackhawks" so..  Anyways, I recall funny ones too like the biology teacher's being "froggy" and the math teacher's being "median" or something silly.  No one used caps, numerics, special characters, or a length of over 6 or 7 characters.

I really didn't expect this to be successful.  I didn't think I'd get anyone's password, let alone nearly all of them.  My first thought was, I need to do the right thing this time around and report this.  But first.. I need to look at a couple of inboxes.  You know, to make sure they're uh.. legitimate?  So I looked at my Math teacher's email and bragged about it the next day.  I tried my hardest to resist the temptation to look at anyone else's.  It felt wrong, but I got that same thrill of gaining unauthorized access from the comfort of my home PC.  I stored the plaintext usernames and passwords in a text file called something obvious like, "My_Teachers_Weak_Passwords.txt" and stored them where I stored everything at that time, my Angelfire web directory!  I didn't want to lose what I had so I figured that was a good a place as any!  It had directory indexing enabled so I could easily see all of my files from anywhere if I needed them.  (pre-cloud, same concept)

At some point I got contacted on my Angelfire email account by an educator at another school, saying they somehow came across my file and encouraged me (felt like a threat) to take it down and self-report the incident.  I explained that I had planned to, but conveniently left out the part about the account access.  Anyways, I went about it completely the wrong way by just walking in the principal's office one day and saying something like, "You all should change your passwords, because they're terrible.".  For some reason they didn't respond well to this.  😲  In my mind I was self-reporting and doing the right thing, but failed to see how this freaked them out at the time.  

They didn't know what to do with me, I was their first "hacking" case.  They wanted to make an example of me but they also had a difficult time understanding the scope of what had been done.  They ended up suspending me for a day and required me to go to a therapist because they decided after the first incident I had an "irresistible urge to hack".  Long story short I went, the therapist was confused as to why I was there, diagnosed me with A.D.D. and sent me on my way.

Trouble at School #3 & #4

I won't waste a lot of time explaining these.  Basically, at this point I had a reputation among the faculty and the other students.  The nickname friends called me was, "Hack".  I didn't like it, but it wasn't meant to be an insult either.  My first computer class was a web design class in 2000 which was run by the PE teacher and he used a Web Development for Dummies book as the curriculum.  No joke!  It was hard to sit through with my experience, so I cloned a fake Ask Jeeves (I was just beginning to be a Google fan) search engine portal and made it respond with a silly answer, no matter what you asked it.  Kind of like what Ask Jeeves did by default, now that I think about it!  My friends and I would call the teacher over and ask why our search wasn't working and get a laugh out of how dumbfounded he was by the whole thing.  Yeah, I was that annoying brat kid when it came to computers.  Anyway, there were two additional incidents that got me sent back to the office.  One time was innocent. I was troubleshooting a DNS issue locally and when the teacher saw the Windows Command Prompt open he instantly thought of the Hollywood movies and deduced I had to be hacking again.  I explained myself to the office staff, but this time I was crying wolf.

The second time in this same class, I realized my workstation was logged in still as an Administrator so I used my new privileges to install a game (Jedi Knight Dark Forces II) on the network share so my friends and I could play multiplayer games instead of designing simple web pages.  I used up all of the free space on the drive, which I thought was allocated for just me.. but instead it was for the entire school.  This caused a bit of a Denial of Service situation accidentally and it eventually got back to me.  This was the final straw for the school and I was banned from computer use for the rest of my high school career.  Little did they know, I was a library assistant so in my free time at the library I would continue to scrape local credentials and install annoying prank-ware like the one that makes your mouse jump all over the place, or the screensaver that looks like a BSOD.. those kind of pranks.  They also had software at that time to "lock down" the computers, so I saw it as a personal challenge to bypass those restrictions, which I had.


I didn't get in trouble for anything in college but I was far from ethical.  I would pirate software and learned how to use a debugger to reverse engineer (RE) the binaries to bypass the need for keys.  I didn't contribute any "cracks" to the community but I enjoyed making them for my own use.  This skill actually came in handy later in my career when reverse engineering malware samples and creating buffer overflows.

I figured out in college how to hack my original Xbox with only software mods, which wasn't something I came up with on my own.  I had followed some guides but I did find a unique way of efficiently cloning new systems in a relatively short amount of time.  To get everything the way I wanted it with roms and cloned games took me about a year.  I found I could replicate the entire process onto a new Xbox in under an hour.  Word got around somehow, and before I knew it I had a bit of an underground business.  Strangers would show up at my door, offer me some cash, and I'd spit out a hacked Xbox for them.  I didn't even advertise anything, it was simply word of mouth.  This would happen somewhat regularly for a while and my roommates were used to it.  I eventually shut this down but continued to mod just about every console I owned afterwards.

Other Memorable Events

Before my career in Cyber Security, I had done other things I was later not proud of.  I hacked into a few of my friend's AIM accounts and pretended to be them to other buddies, thinking it was funny.  When I turned 16 and had access to a laptop I would war drive, which I didn't know was a thing at the time.  One time I was with a buddy and he and I pulled up to his dad's business.  We sat in the parking lot and I showed him how easy it was to access his internal shared folders which contained sensitive documents.

I hacked all of my neighbor's WiFi passwords, especially the ones who had a default 2Wire gateway password of eleven numbers or which leveraged WEP.  I exploited SQL Injection on an e-commerce site and looked around before reporting it anonymously.  I found logic flaws in Marriott's WiFi registration pages which sent pricing information from the client-side, so it was trivial to make it cost $0.00.  I also lived across from a Marriott in an apartment, so with a Pringles cantenna and this I was set.  Similarly, another e-commerce site did this for product pricing, so I actually ordered something and made it cost a dollar only to feel guilt-stricken and cancel the order before it went through.  That was the first time it actually felt like I was going too far, my conscious wouldn't allow it.  However, I did exploit a flash-based "game" on a local car wash's website and created a script to win a free deluxe wash on demand.  I used this many times before it really hit me that what I was doing was also theft and then gave it up.  

Lastly, whenever I'd go somewhere that had a public terminal that was "locked down", I'd try all of the techniques I learned to try to escape the restrictions.  I did this at hotels, lobbies, anywhere there was public access.

Lessons Learned

At that early time in my life in high school, I looked at those events differently.  I viewed myself as a victim, that because of the school administration's ignorance of technology my "harmless snooping" was unjustly being made an example of.  I didn't take down anything or destroy property and I didn't steal anything, I argued that my unauthorized access was the equivalent of walking into the school after hours and simply looking around.  I've had a bad attitude about this event for years and even convinced friends and family along with myself that the school simply didn't understand. 

Let me be clear: I WAS WRONG

I did things without approval.  I created a situation in which people, even friends, no longer trusted me.  I scared the school administration and because this was new to them and they didn't have an "expert" on staff to help them handle the new risk I posed to them, they didn't know how to move forward.  They knew what I had done was wrong and they rightly wanted to prevent this from happening in the future.  Maybe the next person wouldn't simply view records, but change grades and bring down the network?  

Looking back now I would have received greater satisfaction by responsibly asking for permission and testing their deficiencies in order to report them, as I do today as part of my daily job responsibilities.  That rush of doing something I shouldn't and the fear of being caught which follows is nothing compared to the joy that I get from legally testing environments and in turn effectively communicating risk to those customers, to help them strengthen their defenses.  

I genuinely wanted the school to set up better passwords, but scaring them into doing so and violating their trust by accessing accounts I shouldn't have was not the right approach.  

Because of these events, I now have a spot on my record I'm otherwise proud of.  I take great pride in the quality of work I provide to clients and the ethical White Hat road I've stuck to since starting a career in Cyber Security ten years ago.  Don't get me wrong, there are times where I still really want to stick a single quote or an alert(1) in an input field on a site I'm not authorized to test, but I do my best to resist that temptation.

As ridiculous as the idea of therapy for a hacking addiction seems to me, there is a certain truth to the obsession and the difficulty in denying a temptation to test.  I can almost see how someone would become a black hat and internally justify their own actions.  Hacking may seem like a victim-less crime because you can't physically see or get to know the person on the other end of the wire.  

I think a healthy outlet for people in similar situations is to commit full time to the "light side".  Enter a job in Cyber Security as a penetration tester or red teamer, we could use you!  If that's not an option at the moment or it's not enough, there are bug bounty programs available where you're allowed to do testing and get paid to learn in the process!  There's also a plethora of free resources available online where you can test your skills in safe, sandboxed environments.  Capture the flags, intentionally vulnerable virtual machines (Metasploitable, etc), and web applications like DVWA/bWAPP or hackthebox are just a few worth mentioning.  It's certainly no excuse, but these options weren't available back when I started and the media almost seemed to encourage the idea of young hackers instead of condemning it.  It didn't help that Hollywood sensationalized it and still continues to do so today.  I also felt like I was taking this journey alone because that the time I didn't know of other people who were into this.  I certainly didn't think this could be a career if done legally.  I was completely ignorant of "hacker culture" then and as it exists today.

I'm not self-centered enough to think that this blog will turn away black hats that might read this, but I do hope it helps to make others in a similar grey situation as my younger self to think about their actions and to consider the alternative.  It might sound corny, but we have a responsibility to put our skills to good use and fight cyber crime.  We have a vested interest ourselves in making the Internet a safer place, not just for us, but for our friends and family as well.  This field is both financially and self rewarding when we work together collectively to contribute to the overall "health" of our online community.  I'd like to sincerely apologize to the InfoSec community and to the victims of my hacktivities.  I'd like to especially apologize to the Sheridan school system!  I hope this blog finds it's way to those affected individuals.

Thanks for listening to my story!  Please leave a comment if you agree, disagree, or just want to share a similar experience for other readers!  Also, I know what you're thinking and no, you can't have my killer sweater.

- Curtis Brazzell

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