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(684)

7MS #275: Patching Solutions Bake-Off - Part 2

7MS #275: Patching Solutions Bake-Off - Part 2

This episode continues our series on comparing popular patching solutions, such as: Ninite ManageEngine Ivanti PDQ Ninite This week I focused on Ninite, and here's the TLDR version: Pros Does one thing (third party patching) and does it really well Extremely affordable User interface is clean, simple and really easy to use/learn Cons No "agentless" option - it's an agent or nothin' I'm not sure if Ninite has the brand name recognition and reputation to be accepted/respected by large companies I need to do more homework on how they pull down their packages...are they ripping apart packages and repackaging them at all? That could be a big avenue for side-loading icky stuff.

30 Elo 201711min

7MS #274: Speaking at ILTACON - Part 4

7MS #274: Speaking at ILTACON - Part 4

I'm back from Vegas! My talk went really well and I'm excited to tell you about it in today's episode. First, some conference/trip highlights: During the ILTACON conference I attended a great talk by Don McMillan about how to infuse humor into your work environment. Really enlightening, and you know those things you hear about how humor lowers blood pressure, increases satisfaction and just overall makes you a more pleasant person to be around? Turns out it's true! On the day before my presentation I got my first experience touring around the Vegas strip, and the people watching did not disappoint. I also saw the Muhammad Ali and Van Gogh exhibits, which were awesome. When it came to the actual talk, everything went really well. The audio/visual stuff all worked perfect, and I felt the content delivery went over well too. People asked a lot of questions and even hung out afterwards to discuss security topics further. There were two big surprises I wasn't expecting, though: A podcast listener was at the conference, and shared with me that after listening to lots of 7MS episodes, he always figured I looked like Jared from Subway. :-( There were super talented artists from a company called Filament did a comic-book style retelling of my talk live as I was doing it. I love crazy-talented people like this, so I was totally geeking out. I reposted the renderings (with their permission) at my personal portfolio site if you wanna check 'em out.

23 Elo 201715min

7MS #273: Speaking at ILTACON - Part 3

7MS #273: Speaking at ILTACON - Part 3

I ran out of time in episode #272 to tell you about why preparing to be a speaker for ILTACON was way more stressful that preparing for Secure360 a few months ago. The main points of difference/stress were: ILTA wanted to see PowerPoint deck progress weekly, whereas with Secure360 it was pretty much "Your talk is accepted - see you at the conference!" ILTA is going to show a "speaker slide" with bio a few minutes before the sessions starts. That way the session is focused on content (and probably avoids people who like to talk about themselves too much :-) ILTA requested my PowerPoint and handouts a few weeks before the session so they could put on their Web site for attendees to see. Although that put some pressure on me to get content done early, I think it's great because presumably some people at the talk will have screened the content and therefore be more tuned in.

17 Elo 20179min

7MS #272: Speaking at ILTACON - Part 2

7MS #272: Speaking at ILTACON - Part 2

This is part 2 of a series focusing on public speaking - specifically for the ILTACON conference happening in Vegas this week. In this episode I share a high-level walkthrough of my talk and the 10 "Blue Team on a Budget" tips that the talk will focus on. These tips include: Turning up Windows auditing and PowerShell logging Installing Sysmon Installing Security Onion Don't put too much faith in endpoint protection Keep an eye on Active Directory Install RITA Deploy a Canary Use strong passwords Install LAPS Scan and patch all your things

17 Elo 201711min

7MS #271: Patching Solutions Bake-Off - Part 1

7MS #271: Patching Solutions Bake-Off - Part 1

Seems like every business I meet with needs some sort of help in the patching department. Maybe they've got the Microsoft OS side of the house under control, but the third-party stuff is lacking. Or vice-versa. Either way, the team I work with is excited to kick the tires of some popular patching solutions over the next few weeks, and we'll audibly barf up what we learn into this mini-series! Solutions we'll poke around with include: Ninite ManageEngine PDQ Deploy PS: None of these solutions are sponsoring 7MS. They're just popular patching solutions we're trying out to learn more about 'em and give you the pros/cons we discover! In today's episode I dive a bit into... Ninite Pros Cheap Does one thing, and does it well Been around for a long time Cloud-based - doesn't rely on LAN-side server Cons Only cloud-based...no LAN-side option Requires an agent Agent's only purpose is patching - no extra bells/whistles like remote control or inventorying capability

10 Elo 201710min

7MS #270: IDS on a Budget - Part 4

7MS #270: IDS on a Budget - Part 4

I spent a bunch of time with Security Onion the last couple week's and have been lovin' it! I ran the install, took all the defaults, ran the updates, and pretty much just let it burn in on my prod (home) environment. After a few days, I went back to check the Security Onion dashboard to check the alerts. There was a bunch of benign stuff (computers pinging each other, Dropbox broadcasting to the network) but also a couple interesting finds - SO caught one of my VMs downloading (intentionally) Invoke-Mimikatz. The dashboard allows you to see transcripts of file downloads like this, as well as a tool called Network Miner to extract a copy of the downloaded file for further analysis. One thing the SO didn't pick up on was the DNS-based C2 tunnel I setup on a test victim client. However, it turns out RITA works great for exactly this type of analysis - it reported the huge number of DNS requests from my victim client to the C2 server. Very helpful info for an incident response situation!

3 Elo 201712min

7MS #269: Documentation

7MS #269: Documentation

Documentation is super boring, right? Yet it's critical to getting your client/audience excited about making their security better! In this episode I talk about my mixed feelings towards the "big" standards like ISO/NIST/etc. and how a more tactical, down-to-earth documentation approach might be more effective in some cases. And I think we need our documentation to be much more focused on consultation/remediation and not just "Hey, your security sucks...and these next 100+ pages will tell you exactly why!" We can do better! Yes, this episode is like 18 minutes because, well, I guess I'm really passionate about documentation. :-)

27 Heinä 201713min

7MS #268: IDS on a Budget - Part 3

7MS #268: IDS on a Budget - Part 3

Been having a blast working with the beta branch of the Sweet Security project and it anxious to try the latest fixes of the beta branch. Give it a look! I also spent a lot of time the last few nights playing with Security Onion and love it. After zipping through the install wizard and hitting reboot a few times you're pretty much good to go. A few recommendations I'd make after those initial reboots though: Run the soup command to update Security Onion with all the latest packages Use ufw to adjust the internal firewall to allow management from ports other than SSH (which is already preconfigured) On a side note, I think you might have to have your vnic in VMWare set to promiscuous mode in order to allow proper network sniffing. Do a wget http://testmyids.com to ensure Security Onion alerts are coming in the squil dashboard security alerts are pouring in. Also, check out this article for some handy tips on threat hunting with Bro. Next up on my "test this out list" is to setup DNS tunneling to a Digital Ocean droplet I setup, and see if the onion picks up on that, or if I can at least get warned somehow about a high amount of DNS traffic.

19 Heinä 201712min

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