7MS #502: Building a Pentest Lab in Azure

7MS #502: Building a Pentest Lab in Azure

Happy new year friends! Today I share the good, bad, ugly, and BROKEN things I've come across while migrating our Light Pentest LITE training lab from on-prem VMware ESXi to Azure. It has been a fun and frustrating process, but my hope is that some of the tips in today's episode will save you some time/headaches/money should you setup a pentesting training camp in the cloud.

Things I like

  • No longer relying on a single point of failure (Intel NUC, switch, ISP, etc.)

  • You can schedule VMs to auto-shutdown at a certain time each day, and even have Azure send you a notification before the shutdown so you can delay - or suspend altogether - the operation

Things I don't like

  • VMs are by default (I believe) joined to Azure AD, which I don't want. Here's how I got machines unjoined from Azure AD and then joined to my pwn.town domain:
dsregcmd /leave Add-Computer -DomainName pwn.town -Restart
  • Accidentally provision a VM in the wrong subnet? The fix may be rebuilding the flippin' VM (more info in today's episode).

  • Just about every operation takes for freakin' ever. And it's confusing because if you delete objects out of the portal, sometimes they don't actually disappear from the GUI for like 5-30 minutes.

  • Using backups and snapshots is archaic. You can take a snapshot in the GUI or PowerShell easy-peasy, but if you actually want to restore those snapshots you have to convert them to managed disks, then detach a VM's existing disk, and attach the freshly converted managed disks. This is a nightmare to do with PowerShell.

  • Deleting data is a headache. I understand Azure is probably trying to protect you against deleting stuff and not being able to get it back, but they night a right-click > "I know what I'm doing, DELETE THIS NOW" option. Otherwise you can end up in situations where in order to delete data, you have to disable soft delete, undelete deleted data, then re-delete it to actually make it go away. WTH, you say? This doc will help it make more sense (or not).

Things that are broken

  • Promiscuous mode - just plain does not work as far as I can tell. So I can't do protocol poisoning exercises with something like Inveigh.

  • Hashcat - I got CPU-based cracking working in ESXi by installing OpenCL drivers, but try as I may, I cannot get this working in Azure. I even submitted an issue to the hashcat forums but so far no replies.

On a personal note, it has been good knowing you because I'm about to spend all my money on a new hobby: indoor skydiving.

Episoder(689)

7MS #690: Tales of Pentest Pwnage – Part 74

7MS #690: Tales of Pentest Pwnage – Part 74

Today’s tale of pentest pwnage is a classic case of “If your head is buried in the pentest sand, pop it out for a while, touch grass, and re-enumerate what you’ve already enumerated, because that can lead to absolute GOLD!”

29 Aug 21min

7MS #689: Pwning Ninja Hacker Academy – Part 2

7MS #689: Pwning Ninja Hacker Academy – Part 2

Hello friends!  Today your friend and mine, Joe “The Machine” Skeen joins me as we keep chipping away at pwning Ninja Hacker Academy!  Today’s pwnage includes: “Upgrading” our Sliver C2 connection to a full system shell using PrintSpoofer! Abusing nanodump to do an lsass minidump….and find our first cred. Analyzing BloodHound data to find (and own) excessive permissions against Active Directory objects

22 Aug 15min

7MS #688: Building a Pentest Training Course Is Fun and Frustrating

7MS #688: Building a Pentest Training Course Is Fun and Frustrating

Today I talk about a subject I love while also driving me crazy at the same time: building a pentest training course! Specifically, I dissect a fun/frustrating GPO attack that I need to build very carefully so that every student can pwn it while also not breaking the domain for everybody else. I also talk about how three different flavors of AI failed me in solving a simple task.

16 Aug 22min

7MS #687: A Peek into the 7MS Mail Bag – Part 5

7MS #687: A Peek into the 7MS Mail Bag – Part 5

Hi friends, we’re doing something today we haven’t done in a hot minute: take a dip into the 7MinSec mail bag! Today we cover these questions: If I’m starting a solo business venture as a security consultancy, is it a good idea to join forces with other solo security business owners and form a consortium of sorts? Have you ever had anything go catastrophically wrong during a pentest?  Yes, and this is an important link in the story: https://github.com/fortra/impacket/issues/1436 What ever happened with the annoying apartment neighbor who stomped around like a rhino when you made any noise during COVID? What happened to the “difficult family situation” you vaguely talked about a few months ago that involved police and lawyers – did that ever get resolved?

11 Aug 57min

7MS #686: Our New Pentest Training Course is Almost Ready

7MS #686: Our New Pentest Training Course is Almost Ready

Oh man, I’m so excited I can hardly sleep. Our new three-day (4 hours per day) training is getting closer to general release. I talk about the good/bad/ugly of putting together an attack-sensitive lab that students can abuse (but hopefully not break!), and the technical/curriculum-writing challenges that go along with it.

1 Aug 23min

7MS #685: The Time My Neighbor Almost Got Scammed Out of $13K

7MS #685: The Time My Neighbor Almost Got Scammed Out of $13K

Today’s kind of a “story time with your friend Brian” episode: a tale of how my neighbor almost got scammed out of $13k.  The story has a lot of red flags we can all keep in mind to keep ourselves (as well as kids/friends/parents/etc.) safer from these types of shenanigans.

25 Jul 22min

7MS #684: Pwning Ninja Hacker Academy

7MS #684: Pwning Ninja Hacker Academy

Hey friends, today we start pwning Ninja Hacker Academy – cool CTF-style lab that has you start with no cred and try to conquer domain admin on two domains!

18 Jul 22min

7MS #683: What I'm Working on This Week - Part 4

7MS #683: What I'm Working on This Week - Part 4

This week I’m working on a mixed bag of fun security and marketing things: A pentest I’m stuck on My latest lab CTF obsession: Ninja Hacker Academy A cool “about 7MinSec” marketing video that was recorded in a pro studio!

12 Jul 30min

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