Practical Purple Teaming: The Art of Collaborative Defense - podcast episode cover

Practical Purple Teaming: The Art of Collaborative Defense

Mar 15, 202619 min
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Episode description

A comprehensive guide for improving organizational security through the collaborative integration of offensive and defensive strategies. The text details various emulation methodologies, ranging from isolated atomic test cases to complex, scenario-based attack chains that mimic real-world adversaries. It provides technical instructions for utilizing modern security tooling such as MITRE Caldera, Mythic, and Splunk to validate detection capabilities. Beyond technical execution, the source emphasizes the importance of structured reporting and the evaluation of people, processes, and technology. Ultimately, it aims to help security professionals harden defenses by identifying and remediating visibility gaps across enterprise environments.

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Transcript

Speaker 1

Okay, so picture this. You're looking at a book cover and it's got this incredible, uh, really vivid illustration on it. On one side, you've got a knight in full red armor wielding a massive sword that is literally on fire.

Speaker 2

Yeah, it is a very cool cut, it really is.

Speaker 1

And on the other side there's a knight in blue armor holding a sword made of solid, jagged ice. They are locked in combat. Sparks flying fire versus ice. It's like the ultimate battle scene.

Speaker 2

It's a striking image for sure, and honestly, for anyone working in cybersecurity or even just you know, watching movies about hackers, that image that red versus blue is the traditional view of how the world works. Right. You have the red team, the attackers, trying to break in, and the blue team, the defenders, trying to stop them.

Speaker 1

Exactly. It's the classic wargame scenario, right.

Speaker 2

Good versus evil, attack versus defense. But today we are doing a deep dive into a source that asks a pretty radical question. What happens if those two knights stop trying to kill each other? What if instead of swinging those swords, they actually sat down, took off their helmets and started comparing notes in real time. That is the

core premise of practical purple teaming by Alfie Champion. It sounds simple, almost counterintuitive, but the answer to your question is that you get something much more dangerous to the actual bad guys. Okay, you get resilience.

Speaker 1

I love that. So today we are unpacking purple teaming. And just to be clear right off the bat, because I know we have listeners from all over the industry, this isn't about hiring a new purple team to sit between the red and blue ones, right right, Like we aren't telling companies to go out and build a whole new department.

Speaker 2

Yeah, absolutely not. And the source is very emphatic about this. Purple teaming is a methodology. It's not a separate team, got it. It's a functional shift where the offensive side, the ethical hackers, and the defensive side of the security operation center, they collaborate openly. Okay, so the goal shifts from beating the defender to collaborating with the defender to maximize cyber resilience.

Speaker 1

It sounds so logical, but you know, as we went through champions Book, it became clear that this is actually a mass of shift in mindset. It really goes against the grain of how this industry has operated for decades oh completely. So to really get why this matters, I think we have to look at the old way. When we talk about traditional red teaming. What does that dynamic usually look like?

Speaker 2

What traditional red teaming is designed to be a realistic simulation of an adversary. The red team acts like the enemy. They hide their tracks, they operate in secret, and they try to break in without being caught. And crucially, the blue team often doesn't even know the test is happening.

Speaker 1

So it's a surprise attack like a stress test precisely.

Speaker 2

And while that has value, I mean you need to know if you can be surprised, it often creates a zero sum game. Yeah, think of the psychology there. If the red team wins, if they break in and steal the CEO's password or encrypt the database, the blue team feels like they failed. It could be incredibly demoralizing. It creates this ego friction where Red thinks they are geniuses and Blue feels incompetent.

Speaker 1

Right, nobody likes being tricked, especially when it's literally your job to stop the trick. But beyond the feelings, the source highlights a major operational inefficiency here, which is the feedback loop.

Speaker 2

Right. This is the critical flaw in the traditional model. If I'm on the red team and I hack you on Monday, I usually don't tell you about it immediately. Oh wow, I finished my operation. I read a report. You might not find out about the hack until I present that PDF three weeks.

Speaker 1

Later, which is just a massive document sitting on a desk that nobody wants to.

Speaker 2

Read exactly, and by then the digital evidence might be gone, the logs rotated out. The context is lost. In purple teaming, transparency is the weapon. Okay, the offensive team shares their plan. They say, I'm going to run this specific attack at this specific time, using this specific technique.

Speaker 1

I have to play Devil's advocate here. Though, that seems like cheating, doesn't it. If I tell you I'm going to punch you, it's easier to block. Are we actually testing anything? If we give the answers away?

Speaker 2

It feels like cheating if your goal is just to win the exercise. Oh but if your goal is to learn, it's a shortcut. This leads to the aha moment of purple teaming, shortening the feedback loop instead of waiting weeks for a report. The defender watches the attack happen in real time. If they miss it, they can say, hey, I didn't see that alert. Can you run it again?

Speaker 1

Run it again? That really is the magic phrase, isn't it? It changes everything it is.

Speaker 2

You can tweak your defenses on the fly, maybe ad just a firewall rule, or change a detection logic and retest immediately. Wow. That is exponentially faster than waiting for a yearly audit. You are fixing the hole while the person who found it is standing right there.

Speaker 1

It's the difference between taking a final exam and having a tutor sitting next to you explaining the answers as you go.

Speaker 2

Great analogy.

Speaker 1

Yeah, Now, before we get into the how I want to distinguish this from other terms or listeners might know. We hear about vulnerability assessments and penetration tests constantly. Where does purple teaming fit in that line? Dscape?

Speaker 2

Good question, that's important to draw the lines. Think of a vulnerability assessment like walking around a building checking for unlocked doors. It's usually automated scanning for unpatched software. It's broad covering everything, but it's very shallow. It just tells you the door is unlocked, not what is inside, got it?

Speaker 1

And a penetration test.

Speaker 2

A pin test is usually focused on finding flaws and one specific thing, like a new web app or a specific server. It's deeper, but it's still often about can we get in. It stops once they prove they can break the lock.

Speaker 1

And the source mentions assumed breach testing.

Speaker 2

That sounds ominous, Yes, assumed breach is where you skip the hard part of getting in. You assume someone clicked a phishing email or a laptop was stolen. You start the test from the inside. That is often where purple teaming shines because you can focus entirely on detecting movement inside the network, which is where the real damage happens.

Speaker 1

Because realistically, eventually someone is going to click the line.

Speaker 2

Someone always clicks the line, So purple teaming asks, once they are inside, can we catch them before they steal the crown jewels?

Speaker 1

Right? So we know how they work together conceptually, but practically, if you put a hacker and a corporate security officer in a room, they might be speaking different dialects entirely.

Speaker 2

Oh absolutely.

Speaker 1

The hacker is talking about exploits and shell code, the defenders talking about compliance and tickets. The source material spends a lot of time on frameworks to bridge this.

Speaker 2

Gap it does without a common language, this collaboration falls apart and the absolute standard, the Rosetta stone for this is itri Att and.

Speaker 1

Ck Periodic Table for hackers.

Speaker 2

It really is itr Att and Ck catalogs known adversary behaviors based on real world observations gives us a matrix across the top. You have tactics. These are the adversaries high level goals.

Speaker 1

So the tactic is the what are they try and do, like I want to skal data or I want to shut down the system.

Speaker 2

Correct tactic equals goal things like initial access, execution or exfiltration. And underneath each tactic are the techniques the how okay, the goal is initial access, the technique might be phishing or exploiting a public facing application.

Speaker 1

And then it drills down even further right.

Speaker 2

Yes, down to procedures, which are the specific tools or steps used. So we have PTPs, tactics, techniques and procedures.

Speaker 1

Why is the structure so vital for purple teaming, specifically.

Speaker 2

Because it removes ambiguity instead of the red team saying we did some hacking stuff and got your passwords. They can say we executed technique T one O five nine command and scripting interpreter using PowerShell.

Speaker 1

That's way more specific.

Speaker 2

Exactly. The Blue team can then look up T one O five to nine in their own database. It aligns the attack with the defense. It turns magic into a catalog number.

Speaker 1

And connected to This is my absolute favorite concept from the book. It's a visual that explains why we do all this work. The Pyramid of pain.

Speaker 2

It sounds like a wrestling move, it really does.

Speaker 1

Welcome to the Pyramid of Pain, but it's actually about how much you can annoy a hacker.

Speaker 2

Right. It represents the difficulty we inflict on an attacker when we block them. Visualize a pyramid. At the wide bottom. You have things that are trivial for an attacker to change, things like hash values and IP addresses.

Speaker 1

Right, So if I block an attacker's IQ address, I might feel good about myself. I stop them, But what does that actually do to them?

Speaker 2

To them, almost nothing. They just route their traffic through a different server, takes them seconds. It causes them zero pain. It's like change in a burner phone.

Speaker 1

So we're basically playing whack a mole at the bottom of.

Speaker 2

The pyramid, exactly moving up the pyramid, you have domain names, then network and host artifacts, things like specific file names or user agent strings. These are a bit harder to change, but still manageable for a sophisticated attacker.

Speaker 1

But then we get to the top, the point to end the pain zone.

Speaker 2

Tools and TTPs. If you can detect and block the tools they use, they have to go find or build new software. That is expensive, that takes time. But if you can detect the TTP, the behavior itself, that is the pinnacle.

Speaker 1

Can you give me an example of a TTP versus a tool, because I want to make sure I really get this.

Speaker 2

Okay, Let's say the TTP is credential dumping. The attacker wants to steal login information from the computer's memory. There are fifty different tools to do this. Mimicats is a famous one. If you block mimicats, the tool the attacker just uses a different script. But if you detect the behavior of a program trying to touch the memory of the security subsystem.

Speaker 1

Then it doesn't matter what tool they use exactly.

Speaker 2

You've blocked the technique. To get around that, the attacker has to invent a completely new way of stealing credentials. You're forcing them to relearn their tradecraft. You're making their job incredibly.

Speaker 1

Difficult, and that is the goal of purple teaming. We want to live at the top of the pyramid of pain. We want to make their lives miserable.

Speaker 2

We do. We want to make the cost of hacking us higher than the value of what they're trying to steal.

Speaker 1

So we have the language mitre and the goal the pyramid. Now let's get into mechanics. The source outlines two main methodologies for actually running these exercises, scenario based and atomic on.

Speaker 2

Very different they are, and they serve different purposes. Think of scenario based purple teaming like a movie plot. It follows a narrative arc. We call this an activity thread.

Speaker 1

Okay, set the scene for me. What is the plot?

Speaker 2

Action? A user clicks a phishing email in hr malware executes, the attacker performs reconnaissance to see where they are. Then they move latterly to a finance server. Finally they exfiltrate sensitive data. It connects the dots across the entire kill chain from start to finish.

Speaker 1

Show It test the whole story.

Speaker 2

It tests the people and the processes. This is crucial. Can the security operation center handle the volume of alerts? Do they panic when they see the attacker moving laterally? Do they know who to call? Do they escalate to the right manager.

Speaker 1

It's a fire drill, it is, but as.

Speaker 2

You can imagine, it's pretty heavy to set up. You need a script. You need the red team acting continuously, you need the Blue team monitoring. It's a production. It takes time and resources. You can't do that every day.

Speaker 1

Which brings us to the second method, which seems much more agile, Atomic purple teaming.

Speaker 2

Atomic is like the science lab. You isolate one specific variable. Champion calls this de chaining. You take a single link out of that kill chain, sage just credential dumping, and you test it in a vacuum.

Speaker 1

So no story mode, just the mechanics.

Speaker 2

Right. You run the attack, see if you catch it, fix the rule, and run it again.

Speaker 1

This seems perfect for what the book calls performance benchmarking.

Speaker 2

Yes, it's fast, repeatable, and very easy to automate. You can run an atomic test for process injection every Tuesday morning if you want, just to make sure your sensors are still working.

Speaker 1

Wow, Every Tuesday Yeah.

Speaker 2

It answers the question did we get better at spotting this specific bad thing since last month?

Speaker 1

Let's make this real for the listener. The book has this great example about a very specific problem finding out who the administrators.

Speaker 2

Are the discovery tactic.

Speaker 1

Right, So I'm an attacker, I have landed inside the network. I want to know who holds the keys to the kingdom. I want to find the domain admin's groups so I can target them. How many ways can I ask that question?

Speaker 2

This is where the atomic methodology really shines because it exposes the gaps. The book lays out a test suite. First, there's the classic way. You're on a Windows machine. You open the command prompt and you type net group, domain admins.

Speaker 1

Simple, old school.

Speaker 2

Very old school. Most security tools will catch that instantly. It's loud and obvious. But then method two you use a PowerShell script to query active directory, same question, different languages, okay. Method three use a specific hacker tool, something like adfind. This is tricky because adfind is a legitimate tool often used by sitzidmins to manage the network, but it's beloved it by attackers because it blends.

Speaker 1

In so it looks like normal traffic.

Speaker 2

And method four self using living off land binaries or executing code directly in memory, so nothing touches the hard drive.

Speaker 1

So here is the million dollar question. If I am the blue team and I write a detection role that says alert me, if anyone types net group domain admins, am I safe?

Speaker 2

You are saved from the lazy attacker who uses method one. You're completely blind to methods two, three, and four. And that is a terrifying realization for many organizations. They think they are covered because they've blocked the first thing they thought of.

Speaker 1

And this leads to a concept. The expert in the book and really the industry emphasizes capability abstraction. This is a bit technical, but I think it's the most important takeaway of the deep dive. Can you break that down?

Speaker 2

Yes, capability abstraction is the antidote to the whack a mole problem. We just listed four different ways to find the admin's net dot ex, a PowerShell adfind in memory execution. To a human, these look like four different tools, right.

Speaker 1

One is a command, one is a script, one is a program.

Speaker 2

But to the computer, to the network controller, they are all doing the same underlying thing. They're asking the domain controller for a list of users. They're likely using the same protocol like ld app or a sam.

Speaker 1

So capability abstraction means looking at what is happening under the hood, not just the shiny paint.

Speaker 2

On top exactly. If you can detect the ld app query that requests the domain admin list, you catch all four methods with one rule.

Speaker 1

Wait, really, one rule catches all of them, yes.

Speaker 2

Because they all have to ask the question. If you detect the question being asked, you don't care if they use a megaphone, a whipper, or a handwritten note. You caught the intent. That is the power of purple teaming. It stops you from chasing tools and helps you detect the underlying behavior.

Speaker 1

That is a light bulb moment. Stop chasing a tool, chase the behavior. It seems so obvious once you say it, but getting there requires that deep technical collaboration precisely.

Speaker 2

And you only get there if the red team, who knows the tools talks to the blue team, who knows the logs.

Speaker 1

Okay, so we are running these tests, we're firing off LDPP queries, we're checking logs, but we have to talk about the humans in the room, the logistics and human element section of the source material was surprisingly focused on just sitting together.

Speaker 2

Communication is critical. If you are doing your Purple Team extra you shouldn't be emailing each other. You should be in the same room or at least on a dedicated video call or slack channel.

Speaker 1

Shoulder surfing is the term they used.

Speaker 2

Yes, it's literal. The Blue team members should literally be looking over the shoulder of the Red team member as they type the command A enter now, and then the Red team members should walk over and look at the Blue team's screen to see what the logs look like.

Speaker 1

That transparency level is interesting. Do you tell the Blue team exactly what is coming, like, Hey, I'm about to run this specific malware at two point zero five pm?

Speaker 2

Usually yes, full transparency is better for learning. If you want to test surprise, do a Red team engagement. If you want to test detection logic, tell them exactly what you are doing.

Speaker 1

Makes sense.

Speaker 2

You don't want the Blue team wasting three hours wondering if an alert is a false alarm. You want them digging into the data immediately to see why it fired or why it didn't.

Speaker 1

And you have to write this down. You can't just say, oh, it worked.

Speaker 2

Data is everything you need to track success. The book mentions tools like v ectr, which is designed for this and visualizes the results, but honestly, a simple jar at ticket or a shared Excel sheet works too. You need to record the outcome and.

Speaker 1

The metrics aren't just pass fail, are they.

Speaker 2

No, it's nuanced. Did we block it, that's a win. Did we detect it but not block it, that's okay. At least the alarm rang. But maybe we can do better. Or was it silent?

Speaker 1

That silent categories the stuff of nightmares.

Speaker 2

It is did the attack happen and we saw absolutely nothing, no logs, no alerts, silence. That is the danger zone. That means you are bleeding and you don't know it.

Speaker 1

But finding those silent gaps is the whole point of the exercise.

Speaker 2

It is you'd rather find the silence now with your colleague then later with a real attacker. And this brings us back to that cultural shift we started with. We have to move away from the ego battles, right.

Speaker 1

The I gotcha moments, the gotcha culture Exactly.

Speaker 2

The goal isn't for the red team to win. The goal is for the blue team to get better. If the red team breaks in, steals the data, and nobody learns anything because they're too busy arguing or hiding the fail The exercise was a total waste of money.

Speaker 1

It's about leaving the ego at the door, you know. Looking at all of this, the frameworks, the atomic tests, the collaboration, it really feels like the industry growing up. It's moving from night swinging swords to scientists in the lab improving the immune system of the company.

Speaker 2

That is a perfect analogy. It's moving from combat to engineering. We are engineering resilience.

Speaker 1

So to recap our deep dive Today. Purple teeming isn't a new department. It's a new way of collaborating. It's using frameworks like year ATT and c K to speak the same language. It's aiming for the top of the pyramid of pain to block behaviors, not just tools. And it's using atomic tests to validate your defenses continuously.

Speaker 2

And doing it continuously is key, not once a year, but treating it as a constant cycle of improvement, because the attackers aren't taking days off.

Speaker 1

Now. Before we let you go, there was one thought in the source material that really stuck with me. It was about the adversaries themselves. We often think of hackers as these omnipotent wizards who can do anything.

Speaker 2

Ah. Yes, the mention of groups like the Lazarus group right.

Speaker 1

The point was that even the sophisticated attackers, state sponsored groups with millions of dollars, they change their tools constantly. They might compile a new piece of malware every morning.

Speaker 2

Their habits often remain the same. They have muscle memory, just like we do. They prefer certain ways of moving laterally. They have favorite commands for discovery. They are human.

Speaker 1

They like what they know, and that is the challenge we want to leave you with today. If you looked at your organization's security right now, are you blocking IP addresses the stuff that changes every day and causes low pain for the attacker? Or are you hunting for habits?

Speaker 2

Are you hunting for the behavior that forces the adversary to rethink their entire strategy. That is where you want to be.

Speaker 1

That's the Purple Team mindset. Stay curious, everyone, and keep connecting the dots.

Speaker 2

Goodbye,

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