7MS #502: Building a Pentest Lab in Azure

7 Minute Security

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.