7MS #353: Tales of Internal Pentest Pwnage - Part 1

7MS #353: Tales of Internal Pentest Pwnage - Part 1

Buckle up! This is one of my favorite episodes.

Today I'm kicking off a two-part series that walks you through a narrative of a recent internal pentest I worked on. I was able to get to Domain Admin status and see the "crown jewels" data, so I thought this would be a fun and informative narrative to share. Below are some highlights of topics/tools/techniques discussed:

Building a pentest dropbox

The timing is perfect - my pal Paul (from Project7) and Dan (from PlexTrac) have a two-part Webinar series on building your own $500 DIY Pentest Lab, but the skills learned in the Webinars translate perfectly into making a pentest dropbox. Head to our webinars page for more info.

Securing a pentest dropbox

What I did with my Intel NUC pentest dropbox is build a few VMs as follows:

  • Win 10 pro management box with Bitlocker drive encryption and Splashtop (not a sponsor) which I like because it offers 2FA and an additional per-machine password/PIN. I think I spent $100/year for it.

  • Kali attack box with an encrypted drive (Kali makes this easy by offering you this option when you first install the OS).

Scoping/approaching a pentest

From what I can gather, there are (at least) two popular schools of thought as it relates to approaching a pentest:

  • From the perimeter - where you do a lot of OSINT, phish key users, gain initial access, and then find a path to privilege from there.

  • Assume compromise - assume that eventually someone will click a phishing link and give bad guys a foothold on the network, so you have the pentester bring in a Kali box, plug it into the network, and the test begins from that point.

Pentest narrative

For one of the tests I worked on, here were some successes and challenges I had along the way:

Check out the show notes at 7MS.us as there's lots more good info there!

Episoder(499)

7MS #647: How to Succeed in Business Without Really Crying – Part 19

7MS #647: How to Succeed in Business Without Really Crying – Part 19

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7MS #646: Baby’s First Incident Response with Velociraptor

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7MS #645: How to Succeed in Business Without Really Crying - Part 18

7MS #645: How to Succeed in Business Without Really Crying - Part 18

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7MS #644: Tales of Pentest Pwnage – Part 64

7MS #644: Tales of Pentest Pwnage – Part 64

Hey!  I’m speaking in Wanatchee, Washington next week at the NCESD conference about 7 ways to panic a pentester!  Today’s tale of pentest pwnage is a great reminder to enumerate, enumerate, enumerate!  It also emphases that cracking NETLM/NETNTLMv1 isn’t super easy to remember the steps for (at least for me) but this crack.sh article makes it a bit easier!

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7MS #643: DIY Pentest Dropbox Tips – Part 11

7MS #643: DIY Pentest Dropbox Tips – Part 11

Today we continue where we left off in episode 641, but this time talking about how to automatically deploy and install a Ubuntu-based dropbox!  I also share some love for exegol as an all-in-one Active Directory pentesting platform.

27 Sep 202426min

7MS #642: Interview with Ron Cole of Immersive Labs

7MS #642: Interview with Ron Cole of Immersive Labs

Ron Cole of Immersive Labs joins us to talk pentest war stories, essential skills he learned while serving on a SOC, and the various pentest training and range platforms you can use to sharpen your security skills! Here are the links Ron shared during our discussion: VetSec Fortinet Veterans Program Immersive Labs Cyber Million FedVTE

23 Sep 202442min

7MS #641: DIY Pentest Dropbox Tips – Part 10

7MS #641: DIY Pentest Dropbox Tips – Part 10

Today we’re revisiting the fun world of automating pentest dropboxes using Proxmox, Ansible, Cursor and Level.  Plus, a tease about how all this talk about automation is getting us excited for a long-term project: creating a free/community edition of Light Pentest LITE training!

13 Sep 202427min

7MS #640: Tales of Pentest Pwnage – Part 63

7MS #640: Tales of Pentest Pwnage – Part 63

This was my favorite pentest tale of pwnage to date!  There’s a lot to cover in this episode so I’m going to try and bullet out the TLDR version here: Sprinkled farmer files around the environment Found high-priv boxes with WebClient enabled Added “ghost” machine to the Active Directory (we’ll call it GHOSTY) RBCD attack to be able to impersonate a domain admin using the CIFS/SMB service against the victim system where some higher-priv users were sitting Use net.py to add myself to local admin on the victim host Find a vulnerable service to hijack and have run an evil, TGT-gathering Rubeus.exe – found that Credential Guard was cramping my style! Pulled the TGT from a host not protected with Credential Guard Figured out the stolen user’s account has some “write” privileges to a domain controller Use rbcd.py to delegate from GHOSTY and to the domain controller Request a TGT for GHOSTY Use getST.py to impersonate CIFS using a domain admin account on the domain controller (important thing here was to specify the DC by its FQDN, not just hostname) Final move: use the domain admin ccache file to leverage net.py and add myself to the Active Directory Administrators group

7 Sep 202443min

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