Welcome to The Pentester’s 64-Bit AppSec Primer and challenge.

Here at The Pentesters, we have a passion for application security and all that goes with it. We think that application security is an extremely important part of the field of information security and have, “made it our business” so to speak to provide a means of education into modern-day application security. With modern computing becoming more and more advanced, and the requirements for understanding the functionality and security behind said computing becoming equally as challenging to understand, we figured that perhaps giving a set of challenges dedicated to learning the mere basics of 64 bit appsec would be beneficial to the security community.

The 64-Bit AppSec Primer consists of 16 challenges, increasingly more difficult than the previous one, dedicated to learning the basics of 64 bit binary exploitation and reverse engineering. The x64 instruction set, as you would expect, has many new instructions, registers, and calling conventions in comparison to the traditional x86 instruction set. Our goal, with this challenge, is to get you inside a debugger with intentionally vulnerable binaries, and get you looking at the inner-workings of a 64 bit binary. Alongside the increasing complexity of the instruction set, is an equally complexity of exploitation, which as a penetration tester and security engineer, will prove useful to understand.

The challenges consist of varying vulnerabilities and anti-debugger tricks in binaries, such as:

• Stack-based Buffer Overflows
• Format String Vulnerabilities
• Heap-based Buffer Overflows
• Detection of tracing
• Insecure validation of credentials
• and more… don’t want to give you all the good details eh?

As a bonus, we would like to contribute back to the security community. We are donating the VM to Vulnhub, for all to have, and we are also offering prizes to three people who gives us the most robust and complete write-up for the challenges. In order to qualify for the prizes, you must post your write-up on either your personal blog, or website (your choice), and post a link to http://thepentesters.net/challenge/ along with your username. If you are unable to solve all of the challenges, that is okay, we will still accept your write-up for judging, we still want to see what you completed and how you did it. Here are the prizes:

• 1st Place gets $150.00
• 2nd Place gets $75.00
• 3rd Place gets $25.00

The challenge ends on August 31st, 2016. All write-ups must be submitted by then, whoever has written the best write-up with the most detailed explanations wins. The judging will be done by our pentesting team.

Also, I would like to note a couple rules for the reverse engineering challenges.

• The challenge must be solved without attacking the encryption of the flag. Spoiler, I used a basic XOR encryption for most of them so they do not show up in strings. So, that is off-limits. The goal is to break the logic of the application.
• Some challenges have several ways of solving and we would like to see how you did it. My C coding skills are most certainly not expertise, but I feel as if this will prove to be a good exercise for many in regards to exploit development and reverse engineering.
• All else is fair game!

Note: ASLR must be disabled, log in as level17:madpwnage, and run “echo 0 > /proc/sys/kernel/randomize_va_space”. Also, challenge 3, is only a DoS challenge. This is the beta, so there are still glitches. If you find any, please contact me at [email protected] with your discovery.

There are a couple challenges that don’t have “flags” but you will know when you have solved those, please note your findings and take screen-shots of them as well. As for the VM, you are to ssh in as user n00b and password n00b where you will find gdb-peda installed for you to make your life easier. The VM gets its IP through DHCP and is set to host-only adapter in VMware, so it should work for you straight out of the box so to speak. That is all I have for you and I hope you enjoy.

This is a small boot2root VM I created for my university’s cyber security group. It contains multiple remote vulnerabilities and multiple privilege escalation vectors. I did all of my testing for this VM on VirtualBox, so that’s the recommended platform. I have been informed that it also works with VMware, but I haven’t tested this personally.

This VM is specifically intended for newcomers to penetration testing. If you’re a beginner, you should hopefully find the difficulty of the VM to be just right.

Your goal is to remotely attack the VM and gain root privileges. Once you’ve finished, try to find other vectors you might have missed! If you enjoyed the VM or have questions, feel free to contact me at: [email protected]

If you finished the VM, please also consider posting a writeup! Writeups help you internalize what you worked on and help anyone else who might be struggling or wants to see someone else’s process. I look forward to reading them!

This is a boot2root VM and is a continuation of the Basic Pentesting series. This series is designed to help newcomers to penetration testing develop pentesting skills and have fun exploring part of the offensive side of security.

VirtualBox is the recommended platform for this challenge (though it should also work with VMware -- however, I haven’t tested that).

This VM is a moderate step up in difficulty from the first entry in this series. If you’ve solved the first entry and have tried a few other beginner-oriented challenges, this VM should be a good next step. Once again, this challenge contains multiple initial exploitation vectors and privilege escalation vulnerabilities.

Your goal is to remotely attack the VM, gain root privileges, and read the flag located at /root/flag.txt. Once you’ve finished, try to find other vectors you might have missed! If you’d like to send me a link to your writeup, enjoyed the VM or have questions or feedback, feel free to contact me at: [email protected]

If you finished the VM, please also consider posting a writeup! Writeups help you internalize what you worked on and help anyone else who might be struggling or wants to see someone else’s process. There were lots of wonderful writeups for Basic Pentesting: 1, and I look forward to reading the writeups for this challenge.

Description

Much like DC-1, DC-2 is another purposely built vulnerable lab for the purpose of gaining experience in the world of penetration testing.

As with the original DC-1, it's designed with beginners in mind.

Linux skills and familiarity with the Linux command line are a must, as is some experience with basic penetration testing tools.

Just like with DC-1, there are five flags including the final flag.

And again, just like with DC-1, the flags are important for beginners, but not so important for those who have experience.

In short, the only flag that really counts, is the final flag.

For beginners, Google is your friend. Well, apart from all the privacy concerns etc etc.

I haven't explored all the ways to achieve root, as I scrapped the previous version I had been working on, and started completely fresh apart from the base OS install.

Technical Information

DC-2 is a VirtualBox VM built on Debian 32 bit, so there should be no issues running it on most PCs.

While I haven't tested it within a VMware environment, it should also work.

It is currently configured for Bridged Networking, however, this can be changed to suit your requirements. Networking is configured for DHCP.

Installation is simple - download it, unzip it, and then import it into VirtualBox and away you go.

Please note that you will need to set the hosts file on your pentesting device to something like:

192.168.0.145 dc-2

Obviously, replace 192.168.0.145 with the actual IP address of DC-2.

It will make life a whole lot simpler (and a certain CMS may not work without it).

If you're not sure how to do this, instructions are here.

Important

While there should be no problems using this VM, by downloading it, you accept full responsibility for any unintentional damage that this VM may cause.

In saying that, there shouldn't be any problems, but I feel the need to throw this out there just in case.

Contact

This is the second vulnerable lab challenge that I've created, so feel free to let me know what you think of it.

I'm also very interested in hearing how people go about solving these challenges, so if you're up for writing a walkthrough, please do so and send me a link, or alternatively, follow me on Twitter, and DM me (you can unfollow after you've DM'd me if you'd prefer).

I can be contacted via Twitter - @DCAU7

Description

DC-6 is another purposely built vulnerable lab with the intent of gaining experience in the world of penetration testing.

This isn't an overly difficult challenge so should be great for beginners.

The ultimate goal of this challenge is to get root and to read the one and only flag.

Linux skills and familiarity with the Linux command line are a must, as is some experience with basic penetration testing tools.

For beginners, Google can be of great assistance, but you can always tweet me at @DCAU7 for assistance to get you going again. But take note: I won't give you the answer, instead, I'll give you an idea about how to move forward.

Technical Information

DC-6 is a VirtualBox VM built on Debian 64 bit, but there shouldn't be any issues running it on most PCs.

I have tested this on VMWare Player, but if there are any issues running this VM in VMware, have a read through of this.

It is currently configured for Bridged Networking, however, this can be changed to suit your requirements. Networking is configured for DHCP.

Installation is simple - download it, unzip it, and then import it into VirtualBox or VMWare and away you go.

NOTE: You WILL need to edit your hosts file on your pentesting device so that it reads something like:

192.168.0.142 wordy

NOTE: I've used 192.168.0.142 as an example. You'll need to use your normal method to determine the IP address of the VM, and adapt accordingly.

This is VERY important.

And yes, it's another WordPress based VM (although only my second one).

Important

While there should be no problems using this VM, by downloading it, you accept full responsibility for any unintentional damage that this VM may cause.

In saying that, there shouldn't be any problems, but I feel the need to throw this out there just in case.

Contact

I'm also very interested in hearing how people go about solving these challenges, so if you're up for writing a walkthrough, please do so and send me a link, or alternatively, follow me on Twitter, and DM me (you can unfollow after you've DM'd me if you'd prefer).

I can be contacted via Twitter - @DCAU7

Clue

OK, this isn't really a clue as such, but more of some "we don't want to spend five years waiting for a certain process to finish" kind of advice for those who just want to get on with the job.

cat /usr/share/wordlists/rockyou.txt | grep k01 > passwords.txt That should save you a few years. ;-)

Description

Welcome to Moomin's World, one of the best cartoons from the 90's in Nepal. In order to solve this box you require knowledge about the linux command, basic penetration testing along with the tools required during pentesting. Side-by knowledge about the linux process or daemon with some OSINT might come handy and the last part will be some basic concept of Binary Exploitation and the tools required to get your things done. Here you will have to find the total of four flags to become root.

Difficulty level:

It depends upon the skill you have.

Contact

This is my first vulnerable machine. Your feedback is most welcome and really appreciated. You can contact me via twitter and instagram @gr4n173.