I had the chance to take SANS SEC599, “Defeating Advanced Adversaries - Purple Team Tactics & Kill Chain Defenses” last week at SANSFIRE. The class is one of the newer SANS offerings, and so I suspect it will be changing and updating rapidly. There are some things I would change about the class, but overall, I enjoyed the class, definitely learned things that I didn’t know before, and got to meet some really smart people.

Course structure

My Mistaken Impression Coming In

When I look at the title of the class, what got me really excited about it was the “Purple Team Tactics” part. When I think of purple teaming, I think of red and blue working together to start pushing the boundaries of current detection/prevention. When you come to a point where blue can’t detect/prevent the activity, you can then work to configure the environment to bring addition data to the SIEM, generate new alerts / rules, and configure systems to increase logging and close vulnerabilities. And that is what the class taught as well.

Coming in, I had overlooked the second half of the title, “Kill Chain Defenses”. This isn’t necessarily a bad thing, but it led to some confused expectations. Where I had read the class as “Purple Teaming”, it really should have been seen as “Advanced Defence, Achieved Through Both Purple Teaming AND Other Kill Chain Defenses”.


The class structure was set up to spend a block of time walking through each step in the cyber kill chain.

Day 1

The first day, “Knowing the Adversary, Knowing Yourself” was a bit of a mixed bag. There was general overview stuff, a discussion how to set up your space to be defensible, and some information about scanning and open source intelligence gathering, which aligns to step one in the kill chain, reconnaissance.

To be honest, this day was a bit of a disappointment, like every other SANS first day I’ve experienced (except SEC660). There was a fair amount of overview material, and it was a little unfocused. There was a lab where we built a phishing document, and used it to gain access to the target environment, and then stole credentials to a file server and exfilled the secret plans. It wasn’t clear why it was there, other than to make sure everyone could use Kali/Metasploit. Another lab we ran Nessus against an environment to check for vulnerabilities. It’s not that this content isn’t interesting, it’s just that I’ve had it in SEC560, and I’m sure other parts are covered in some of the defensive classes I haven’t taken. By the end of day 1, there was no real purple teaming, other than some discussion of what it was.

Day 2

Day 2 was titled “Averting Payload Delivery”, where we talked about not only phishing, but removable media, and even delivery for lateral movement with attacks like SMB relay using Responder. This day was mostly focused on Kill Chain step 2 and 3, Weaponization and Delivery, though (due to the imperfections in the kill chain, some of the lateral movement stuff could be considered Actions on Objectives).

The labs were all around good. The first lab, using Responder, and then configuring GPOs at the domain controller to enable SMB signing and turn off LLMNR, and then trying again and seeing that the attack is now unsuccessful was exactly what I was hoping to get out of the class. Other labs were good, though not really purple activities. Still, I enjoyed the lab where we used Suricata, Cuckoo, and YARA to build (really, finish building, as most of the work was already done) a sandbox environment for email attachments. In another, we got to set up ELK to detect exploit kit activity.

Day 3

Day 3 was titled “Preventing Exploitation”, and was focused on kill chain step 4, exploitation. We looked at hardening using AD and GPO to restrict scripting, putting whitelisting in place, and setting up logging with Sysmon. We built out queries and visualizations in our ELK SIEM to help see and understand the data. We looked at various protections that EMET can enable. Throughout the day we used purple teaming strategies to identify problems, and then fix them and show that they were fixed. I really enjoyed this day, as it gave me a lot of insight into an area that I was weak in (Windows hardening and configuration, and active directory), and provided the purple team mindset to show the problem, and then show how it was fixed.

Day 4

“Avoiding Installation, Foiling Command and Control, and Thwarting Lateral Movement” aimed to tackle the last three kill chain stages - Installation, C2, and Actions on Objectives. We looked at persistence and autoruns, OSquery, privesc, C2, and lateral movement. It was a lot, and frankly, I think this could have easily been 2 or more days to cover each of these better. A real discussion of detecting and stopping lateral movement could take a full day on it’s own.

In the labs, we got hands on with Autoruns, OSquery, Suricata, Bro. We also did more GPO creation to make lateral movement more difficult.

Day 5

Day 5 continues Actions on Objectives with with “Thwarting Exfiltration, Cyber Deception, and Incident Response”. I thought the exfiltration section was good, but a bit rushed. Then we moved into Cyber Deception. I found this interesting, and I learned from it. However, it also didn’t totally fit into the class, and I might suggest dropping it to do a better job on some of the other sections. Finally, there was a section on IR which was pretty much a waste. IR is something much better handled in the other SANS classes devoted to it, such as FOR508.

Structure Summary

I think the structure of this class was imperfect at best, at least for my needs. It tries to be a little bit of everything, and then ends up rushing through some really interesting parts that could use more coverage.


Technical Setup

The labs were all run through a browser with remote desktop access to various machines. The setup was actually quite slick. For each lab, you’d hit a button to start the lab environment, and a new browser window would open, and it would take 1-2 minutes to load the environment. When the screen would load, there was a virtual machine in the main center window. On the bottom was a bar, with the current instructions for the lab, and a next button to move to the next step. On the right, was a sidebar with each of the machines used in the lab, and the ability to switch to bring them into the main view, as well as shortcuts for ctrl+alt+del, and ways to paste into the vms.

One downside of this configuration is that you don’t get the VMs for the Windows AD environment to take home with you.


Overall, most of the lab content was really good. The course authors did a good job of getting some of the really heavy lifting done beforehand. For example, getting Cuckoo set up is a giant pain. But they took care of all of that for us, and just had us set up the connections between Suricata on the mail server and Cuckoo, and then we loaded Yara rules into the Cuckoo setup. It showed off what we could do, and having us go through all of the pain in class wouldn’t really have helped anyone.

There were about half the labs that were great examples of purple teaming, and I particularly enjoyed those. The other half typically demonstrated some useful defensive capabilities, some of which I will use in my day job.


In my offering, the instruction was one of the course co-authors, Eric Van Buggenhout. He was awesome. He was skilled both technically and as a presenter. He did a good job going through complex material, and mixed in a ton of really corny jokes to keep it light.

His time management was pretty good, though most days we ended the course content with a final lab to go around 5, so plan on an extra 20-30 minutes if you want to do the last lab.


The final CTF consisted of two parts running at the same time. First, there was a jeopardy-style board with questions worth points. At the same time, you had a small network to defend against waves of attacks, and stopping various attacks was worth points. I didn’t catch a rationale behind having two unrelated tasks, but my guess is that it’s to similar the real world, where you are doing your day job and hardening and dealing with attacks all at the same time.

The jeopardy style part really wasn’t even that related to the class material. It had some malware re, some pcap analysis, some trivia, etc. The questions were definitely infosec focused, but not really anything from this class.

I wish I had spent more time thinking out a strategy for defending our network at the start instead of just diving into the questions. Were it up to me, I’d probably cut the jeopardy part entirely. I understand the desire to replicate the real world, but I ended up spending a lot of time on it, and missed out on a chance to use my newly developed skills in the final day.


Overall, I for the most part enjoyed my time in SEC599, and it was worth my time. As with every other SANS class I’ve taken, it was really solid training, by experts in the field, and I walked away with things I can use in my day job.

I do think there are structural flaws in the class, and that it would benefit from some restructure, and perhaps even breaking it into multiple classes. That said, once I got over my expectation that everything be purple team focused, it was really a solid course.