7MS #502: Building a Pentest Lab in Azure
7 Minute Security5 Tammi 2022

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.

Jaksot(683)

7MS #491: Interview with Louis Evans of Arctic Wolf

7MS #491: Interview with Louis Evans of Arctic Wolf

Today we're joined by Louis Evans of Arctic Wolf to talk about all things cyber insurance, including: History on cyber insurance - who's buying it, what it does and doesn't cover, and when it started to be something you didn't want to leave home without What are insurance companies asking/demanding of customers before writing a cyber insurance policy? What basic things organizations can do to reduce malware/ransomware incidents (whether they are considering a cyber insurance policy or not)? How do I evaluate the various insurance carriers out there and pick a good one?

20 Loka 202152min

7MS #490: Desperately Seeking a Super SIEM for SMBs - Part 4

7MS #490: Desperately Seeking a Super SIEM for SMBs - Part 4

Hey friends! Today we're going to recap the SIEM/SOC players we've evaluated so far (Arctic Wolf, Elastic, Sumo Logic, Milton Security) and then talk about a new contender that was brought to our attention: Blumira (not a sponsor, but I'm really digging what I'm seeing/hearing/experiencing thus far)!

13 Loka 202142min

7MS #489: Ping Castle

7MS #489: Ping Castle

Today we're talking about Ping Castle (not a sponsor), an awesome tool for enumerating tons of info out of your Active Directory environment and identifying weaknesses, misconfigurations and paths to escalation! It's wonderful for both red and blue teamers. Some of Ping Castle's cool features include being able find: Kerberoastable and ASREPRoastable users Plain text passwords lingering in Group Policy Objects Users with never-expiring passwords Non-supported versions of Windows Machines configured with unconstrained delegation Attack and escalation paths to Domain Admins

6 Loka 202158min

7MS #488: How to Succeed in Business Without Really Crying - Part 10

7MS #488: How to Succeed in Business Without Really Crying - Part 10

Today we continue our series focused on building a security consultancy and talk about: A phishing campaign that went off the rails, and lessons learned from it First impressions of an awesome tool to help add MFA to your Active Directory (not a sponsor) A tangent story about how my wife brought some thieves to justice!

29 Syys 202143min

7MS #487: Light Pentest eBook Announcement!

7MS #487: Light Pentest eBook Announcement!

Hey friends! Today I've got some exciting personal/professional news to share: our Light Pentest eBook - which is a practical, step-by-step playbook for internal network penetration testing - is now available for purchase! Note: this eBook and the Light Pentest LITE training are two separate things, but do cover some of the same topics. The Light Pentest eBook covers: Grabbing and analyzing packet captures Abusing insecure network protocols Exploiting (the lack of) SMB signing Capturing, cracking and passing hashes Locating high-value targets with DNS zone transfers Exploiting vulnerable Group Policy Objects Scraping screenshots of Web interfaces with WitnessMe Finding and cracking "Kerberoastable" and "ASREPRoastable" Active Directory accounts Dumping, passing and cracking hashes from domain controllers The Light Pentest eBook is available now for $7.77, and by purchasing it you are entitled to all future editions/revisions going forward.

28 Syys 20217min

7MS #486: Interview with Matt Quammen of Blue Team Alpha

7MS #486: Interview with Matt Quammen of Blue Team Alpha

Today our good buddy Joe Skeen and I virtually sit down with Matt Quammen of Blue Team Alpha to talk about all things incident response! Topics covered include: Top 5 things to do and not do during ransomware event Challenges when responding to ransomware events Opportunities to break into infosec/IR The value of tabletop exercises, and some great ideas for conducting your own Incident response stress and success stories Cyber insurance - worth it or not?

22 Syys 202139min

7MS #485: Interview with Christopher Fielder

7MS #485: Interview with Christopher Fielder

Today our friend Christopher Fielder from Arctic Wolf is back for an interview four-peat! We had a great chat about making sense of vendor alphabet soup terms (like SIEM, SOC, EDR/MDR/XDR, ML, AI and more!), optimizing your SOC to "see" as much as possible, tackling vendor/customer communication problems, and simplifying security product pricing to make purchases less stressful for customers! And don't forget to check out Christopher's first, second and third interviews with 7MS.

15 Syys 202152min

7MS #484: Desperately Seeking a Super SIEM for SMBs - Part 3

7MS #484: Desperately Seeking a Super SIEM for SMBs - Part 3

Today we're continuing our series called Desperately Seeking a Super SIEM for SMBs - this time with a focus on a new contender in our bake-off: Perch Security! It might help you to go back and take in part 1 and part 2, but today we're focusing on the first experience I had chatting with the sales/technical folks at Perch. TLDL: I really liked a lot of things I was hearing and seeing. Pros (perceived) include: Simple pricing model Easy to use dashboard Cool "marketplace" of integrations you can add to your instance and start getting alerts for Nice API integration that seemed pretty simple to use - and that covers a lot of different cloud products and services Ticket dashboard looked straightfoward to use and interpret Can quickly add IPs/subnets that you don't want to monitor, if appropriate

8 Syys 202146min

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