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This is my first boot2root machine. It's begginer-intermediate level.

It's been tested in VBox and VMware and seems to work without issues in both.

A tip, anything can be a vector, really think things through here based on how the machine works. Make a wrong move though and some stuff gets moved around and makes the machine more difficult!

This is part one in a two part series. I was inspired by several vms I found on vulnhub and added a bit of a twist to the machine.

Good luck and I hope you guys enjoy!


This is my first CTF/Vulnerable VM ever. I created it both for educational purposes and so people can have a little fun testing their skills in a legal, pentest lab environment.

Some notes before you download!

  • Try to use a Host-Only Adapter. This is an intentionally vulnerable machine and leaving it open on your network can have bad results.
  • It should work with Vmware flawlessly. I've tested it with vbox and had one other friend test it on Vbox as well so I think it should work just fine on anything else.

This is a Boot2Root machine. The goal is for you to attempt to attempt to gain root privileges in the VM. Do not try to get the root flag through a recovery iso etc, this is essentially cheating! The idea is to get through by pretending this machine is being attacked over a network with no physical access.

I themed this machine to make it feel a bit more realistic. You are breaking into a fictional characters server (named Wallaby) and trying to gain root without him noticing, or else the difficulty level will increase if you make the wrong move! Good luck and I hope you guys enjoy!

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Welcome to another boot2root / CTF this one is called Analougepond. The VM is set to grab a DHCP lease on boot. I've tried to mix things up a little on this one, and have used the feedback from #vulnhub to make this VM a little more challenging (I hope).

Since you're not a Teuchter, I'll offer some hints to you:

Remember TCP is not the only protocol on the Internet My challenges are never finished with root. I make you work for the flags. The intended route is NOT to use forensics or 0-days, I will not complain either way.

To consider this VM complete, you need to have obtained:

  • Troll Flag: where you normally look for them
  • Flag 1: You have it when you book Jennifer tickets to Paris on Pan Am.
  • Flag 2: It will include a final challenge to confirm you hit the jackpot.
  • Have root everywhere (this will make sense once you're in the VM)
  • User passwords
  • 2 VNC passwords

Best of luck! If you get stuck, eat some EXTRABACON

NB: Please allow 5-10 minutes or so from powering on the VM for background tasks to run before proceeding to attack.

Changelog

  • v0.1b - Initial Version
  • v01.c - Fixes for flags based on feedback from mrB3n
  • v0.1d - Fixes based on shortcut to intended route
  • v0.2a - Fixes and clean up of disks for smaller OVA export
  • v0.2b - Small edit to remove copy of flag in wrong folder

SHA1SUM: D75AA2405E2DFB30C1470358EFD0767A10CF1EB1 analoguepond-0.2b.ova

Many thanks to mrB3n, Rand0mByteZ and kevinnz for testing this CTF.

A special thank you to g0tmi1k for hosting all these challenges and offering advice. A tip of the hat to mrb3n for his recent assistence.

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-----BEGIN PGP SIGNED MESSAGE-----

Hash: SHA512

Welcome to

  ___           _            ___          _
 |   \ ___ _ _ | |_____ _  _|   \ ___  __| |_____ _ _
 | |) / _ \ ' \| / / -_) || | |) / _ \/ _| / / -_) '_|
 |___/\___/_||_|_\_\___|\_, |___/\___/\__|_\_\___|_|
                        |__/
                             Made with <3 v.1.0 - 2017

This is my first boot2root - CTF VM. I hope you enjoy it. if you run into any issue you can find me on Twitter: @dhn_ or feel free to write me a mail to:

  • Email: [email protected]
  • GPG key: 0x2641123C
  • GPG fingerprint: 4E3444A11BB780F84B58E8ABA8DD99472641123C

Level: I think the level of this boot2root challange is hard or intermediate.

Try harder!: If you are confused or frustrated don't forget that enumeration is the key!

Thanks: Special thanks to @1nternaut for the awesome CTF VM name!

Feedback: This is my first boot2root - CTF VM, please give me feedback on how to improve!

Tested: This VM was tested with:

  • VMware Workstation 12 Pro
  • VMware Workstation 12 Player
  • VMware vSphere Hypervisor (ESXi) 6.5

Networking: DHCP service: Enabled

IP address: Automatically assign

SHA-1:

77439cb457a03d554bec78303dc42e5d3074ff85  DonkeyDocker-disk1.vmdk
d3193cca484f7f1b36c20116f49e9025bf60889c  DonkeyDocker.mf
7013d6a7c151332c99c0e96d34b812e0e7ce3d57  DonkeyDocker.ovf

Looking forward to the write-ups!

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Hacker House are community sponsors at this year’s BSides London 2017 and, to celebrate, we have an exploit challenge for you. A key date in the UK security scene, it offers an alternative technical conference for the hackers and tech geeks to share war stories and learn. We are providing a challenge lab designed especially for the conference that attendees can sink disassemblers into. If you aren’t at the event, you can also hack along at home, but remember that prizes for solutions can only be claimed at our stand during the event! The challenge is provided in ISO format which you can boot in VirtualBox or any similar virtualisation software, heck you can even run it on an ATM if you like, but this is unsupported. If you solve our little brain teasing conundrums and beat the system to get root, the first three successful solutions presented to us at our stand can claim one of our awesome hoodies, check them out in our shop! This challenge is open to individuals, but if you do decide to team up, then let us know as only one prize can be claimed per solution. We are also giving several t-shirts away during the raffle so make sure you get your tickets!

Our challenge will test your elite hacking skills and requires web application, reverse engineering, cryptography and exploit abilities. It shouldn’t take the competent skilled hacker too much time, but if you do struggle then watch our social media feeds during the event for some tips to this adventure. You should run the challenge in Host-Only networking mode and on successful boot you will be presented with a console, similar to the one shown at the end of this post. You should solve the challenge from a network perspective, only solutions using this route will be accepted for prizes (unless they are really cool!).

The goal of the challenge is to hack the ISO, level up your skills and get root, come and show us how you did it if you want to claim your prize! If you are struggling with the configuration of our challenge, you can check out our training course free module, which details steps for configuring a similar lab. You can find details and upcoming dates of our training here.

Happy hacking and remember sharing is caring so post (tweet us @myhackerhouse!) or email a solution and let us know about it after the event. We will share links to the best of them on this blog! May the force be with you, young padawan, and remember that hacking isn’t just a skill – it’s a survival trade.

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