Red Team Development and Operations: A practical guide

Ever wonder how prepared, like really prepared your organization is for a.

Cyber attack, like not just checking the box, yes.

Yeah, like actually facing down a real threat.

Yeah.

That's where red teaming comes in exactly. It's like ethical hacking on steroids. We're diving deep into the book Red Team Development and Operations.

Great book.

Think of it as our playbook for understanding this whole world.

It's a fascinating world because red teaming goes way beyond just like finding a vulnerability, Okay, you know, it's about understanding how an attacker would actually exploit those weaknesses. Kind like a stress test for your security, but instead of just looking at technical specs, it simulates a real attack scenario.

Okay, so let's say someone is listening and they're thinking, all right, but isn't that what penetration testing is for.

Yeah, so pen testing is definitely a part of it, but red teaming takes a much broader view. Okay, Okay, imagine security is like a fortress. Okay, pen testing might if the walls are strong. Red teaming is trying to sneak in, maybe disguised as a delivery person, or even digging a tunnel underneath.

Wow.

It tests the people, processes, and technology all at once.

That's a great analogy, and it reminds me of the story from the book about a company where the leadership just assumed that only five people had access to their accounting systems, but when the red team came in.

Yeah, they found a bunch more people who actually had access, which obviously creates a much bigger security risk. It's a classic example of how red teaming challenges assumptions. It forces you to look beyond the obvious and consider all the potential attack vectors.

So it's not about if you have a weaknesses, it's about how an attacker would actually exploit them and what would happen if they did exactly.

And that brings us to a really helpful visual. The book uses the inverted triangle. It shows the relationship between vulnerability assessments, penetration testing, and red teaming. At the very top, you've got vulnerability assessments. Think of this is casting a wide net to find as many potential weak points as possible. It gives you a broad overview but doesn't go into a lot of depth.

Okay, that makes sense. So it's like a basic scan to identify the low hanging fruit.

Then what Then you move down the triangle to penetration testing. This is where you actually try to exploit those vulnerabilities. You poke and prod to see if you can actually get in. It's a deeper dive, but still primarily focused on technical weaknesses.

And then at the very bottom of the triangle the tip yep, that's where red teaming comes in.

Exactly. Red teaming encompasses all of it. You're looking at the vulnerability scans, the penetration test results, but you're also factoring in the human element. Okay, how do employees respond to phishing attempts? Are there gaps in security procedures? Could someone literally tailgate their way into a secure area? It's about seeing how the entire system, people, processes, and technology would hold up against a determined attacker.

Okay, so it's like a full blown simulation of real world attack taking everything into account. That's pretty intense. But how do they even begin to plant something like that? Do they just pick a random attack scenario and go for it?

Not at all. Red teams use threat intelligence and frameworks like mitre, ATT and CK to understand real world tactics and techniques. Basically, they create a profile of the threat they're simulating based on real world adversaries.

So instead of just throwing spaghetti at the wall and seeing what sticks, they're actually studying the playbook of real attackers and saying, Okay, how would this group target our organization?

You got it? And they don't try to simulate everything at once. The book calls it decomposing the threat. They break down a complex adversary into their core components. What are their goals, what tactics are they known for, what tools do they use? This helps them focus on what's feasible within the time and budget constraints of.

The engagement, right because you can't simulate every single aspect of a sophisticated attack, but you can focus on the key elements that are most elevant to the organization you're testing. So let's say they've identified the threat they want to emulate. What happens next.

This is where it gets really interesting. Red teams have to decide what type of engagement they're going to conduct. There are two main types, announced and unannounced.

Wooh unannounced that sounds like it could get a little spicy.

They can with an announced engagement, the organization knows the test is coming. They might be a little more prepared, maybe they've patched some known vulnerabilities where they're on high alert for phishing emails.

So it's more of a controlled experiment exactly.

But unannounced engagements, those are designed to be more like a real attack. Okay, the organization has no idea its coming, so they're caught completely off guard.

Wow, that must be a real eye opener for them. You get to see their true reactions and how well they would actually respond to a real world attack exactly.

And the book has this Red Team tip that I love. It says unannounced engagements are best for understanding overall security operations effectiveness, while announced engagements are better for testing specific capabilities. So if you want to see how your incident response team would handle a ransomware attack, an announced engagement might be a better fit. But if you want a truly realistic assessment of your overall security posture, unannounced is the way to go.

It's like the difference between a fire drill and an actual fire. Right, one is a practice run, the other is the real deal.

That's a great way to put it. And then there's another type of engagement that's worth mentioning. The assumed breach model. Okay, this is where the red team is given initial access to the system. They skip the getting in part and go straight to seeing what they can do once they're inside.

Hold on. So it's like saying, Okay, we know someone could get in, so let's just focus on what happens next. Isn't that a bit risky?

It can be, but it's also incredibly valuable for understanding an organization's ability to detect and respond to an active threat. It's like saying, Okay, the alarm bells are already ringing. Now let's see how quickly and effectively you can contain the damage.

So it's about understanding how far an attacker could get once they're passed the initial defenses. That makes a lot of sense, but it does raise another question. If they're already inside, how do they actually operate without getting caught?

Right?

I mean, isn't there a ton of monitoring and security software that would pick up on unusual activity?

Absolutely, that's where tradecraft comes in. The art of stealthy operations. Red teams are all about being as quiet and undetected as possible. I think ninja's of the cybersecurity world. They have to blend in, avoid detection and minimize their footprint. They don't want to tip anyone off that they're.

There, so they're not just brute forcing their way in. They're being strategic and careful about every move.

They make exactly. For example, they might minimize callback volume to avoid detection by network monitoring tools. Instead of constantly sending data back and forth, which could raise red flags, they'll try to limit their communication as much as possible.

So it's not just about what they do, it's about how they do it. It's about being stealthy and understanding how to operate under the radar. If that raises the question, how do they actually get commands to their tools once they're inside.

It's a great question, and it gets into some of the more advanced tactics that red teams use. Okay, we'll dig into that more in just a moment.

Okay, so we've covered a lot of ground here. We've talked about what red teaming is, the different types of engagements, and even a bit about the tradecraft involved. But before we go, let me ask you this, why should someone listening care about all of this? I mean, if you're not a security professional, doesn't really matter.

It absolutely matters, because here's the thing. Red teaming isn't just about protecting organizations. It's about protecting you. Think about all the data you have stored online. Your bank accounts, your social media profiles, your medical records, all of that is potentially vulnerable.

To attack, right, And even if you're not a target yourself, you could be collateral damage in a larger attack, right, Like if a company you do business with gets hacked, your data could be compromised exactly.

So understanding how red teaming works gives you a better understanding of the threats you face and how to protect yourself. It's about being aware of the risks and taking steps to mitigate them.

So it's not just about technology, it's about awareness and education and maybe a little bit of healthy paranoia. We'll be back in just a moment to continue our deep dive into red teaming. Don't go anywhere.

Looking forward to it. So before the break, we were talking about how red teams stay stealthy once they're inside a system, right, right, And it reminded me of this passage in the book that talks about how even a simple command can be a giveaway if you're not cures.

Wait, really, like, what kind of command are we talking.

It's a great example because it shows just how detail oriented red teams have to be. Okay, the book mentions the netstack command, which is used to display network connections. Okay, it seems pretty basically yeah, yeah, but the thing is it behaves differently on Windows and Linux systems.

Uh huh.

So if a red teamer is operating on a Windows system but accidentally uses the Linux version of the command, oh, I see, they've blown their cover. It's a dead giveaway that something's not right. Wow, and that's just one tiny example. Yeah. Red teamers need to be incredibly meticulous and have a deep understanding of the tools and systems they're working with.

It's like they have to be fluent in multiple computer languages, but instead of speaking, they're typing exactly, and any little grammatical error, yes, could get them caught.

That's a fantastic analogy, and it brings us back to that idea of threat planning and using frameworks like miterre att and CK.

Right.

Remember, it's like a giant catalog of tactics and techniques that real world attackers use.

Right, So instead of reinventing the wheel, red teams can draw on this knowledge base of proven tactics, right, but how does that actually work in practice.

Let's say the red team is emulating a group known for using spearfishing to deliver malware. Okay, they'd start by looking at the att and CK matrix for techniques related to fishing, like spearfishing attachment or spearfishing link.

So they're looking for specific technique that match the adversary they're trying to emulate exactly.

And they wouldn't just copy a technique blindly. They would research those techniques in detail, okay, to understand how they work, what kinds of lures are effective, and what tools and infrastructure are typically used.

So if I'm picturing this correctly, they're going through this massive database of attack techniques, reading about how real attackers have used them in the past, and then figuring out how to adapt those techniques to the specific organization they're targeting.

You're getting it. It's about replicating the specific tactics and techniques of a real adversary, not just finding generic vulnerabilities. And that level of detail is what makes red teaming so effective.

It's like they're writing a screenplay for a cyber attack. Yes, based on a true story, but instead of actors, they're using malware and exploits.

I love that You've got it exactly Now. Once they've chosen their techniques, it's time to start thinking about how to actually tells the organization's defenses. Okay, remember those three main phases we discussed earlier, Get in, stay in, and.

Act right like a cyberheist movie. Yes, first you got to get inside the vault. Then you have to stay hidden long enough to crack the safe, and then you make your move.

That's a great way to think about it. Uh huh, So let's break down each phase. Okay, get in is pretty straightforward. That's the initial point of entry. This is often where social engineering techniques like phishing come into play. The red team might send a carefully crafted email designed to trick an employee into clicking a malicious link or opening an infected attachment.

And we all know how easy it is to fall for a well crafted phishing email. I mean, I've even seen security professionals get fooled by some of these things.

It happens to the best of us, right. Humans are often the weakest link in the security chain, and attackers know that red teaming helps organizations understand how susceptible their employees are to social engineering, and how to train them to be more vigilant.

It's not just looking for technical vulnerabilities and systems. They're looking for vulnerabilities and human behavior as well.

Exactly. It's about understanding how people react under pressure and how to build a security culture that encourages vigilance and awareness.

Okay, so let's say the Red team successfully gains access through a phishing attack. Okay, what happens next? That's the stay in phase, right right.

Once they have a foothold, they need to maintain their access and avoid detection. Okay, this is where persistence comes in. They're essentially setting up shophand finding ways to stay embedded in the system without raising any alarms.

I can only imagine how nerve racking that must be. They're like a secret agent operating behind enemy lines, trying to blend in and avoid detection. But what specific tactics do they use to stay hidden.

They might install back doors, create rogue user accounts, or even hijack legitimate processes to blend in with normal system activity.

So they're basically camouflaging themselves within the system exactly. But all of that must take a lot of technical skill and knowledge.

It does, and it's a reminder that security is not a one time fix. It's an ongoing battle.

Yeah.

Organizations need to be constantly monitoring their systems for suspicious activity and looking for signs of compromise.

Right, because once an attacker is inside, they can potentially lie dormant for months or even years before they actually make their move.

That's right, And that brings us to the final phase act. Okay, this is where the red team actually carries out their objective, which could be anything from stealing sensitive data to disrupting operations to demonstrating that they were able to achieve a specific goal.

It's showtime.

Yeah, but it's not.

Just about proving that they can get in. No, it's about showing what they can do once they're inside and what the real world consequences could be exactly.

And that brings us to one of the most fascinating aspects of red teaming operational impacts. Okay, this is where things can get really interesting and potentially a little uncomfortable for the organization.

Okay, so we're talking about actually simulating the effects of a real world attack, right, what kind of things are we talking about here.

It could be anything from simulating a denial of service attack, to disrupting critical business processes to even manipulating industrial control systems.

Wow, that's pretty intense, but I can see how it would be a powerful way to get the organization's attention and make the risks feel real.

Yeah.

It's like, look, we're not just playing games here. This is what could happen if you don't take security seriously.

That's exactly the point. It's one thing to read a report about a vulnerability. It's another thing entirely to experience the impact of that vulnerability firsthand.

Right. It's like the difference between reading about a fire and actually feeling the heat exactly. It makes it much more real and immediate, exactly.

And that's why operational impacts can be so effective in driving change.

Yeah.

They help organizations move beyond the theoretical realm of risk and into the realm of tangible consequences.

It's like a wake up call, yes, but instead of a loud noise, it's a simulated cyber attack.

I like that. And it's important to remember that the Red Team isn't doing this to punish the organization, right, They're doing it to help them improve their security posture.

So it's not about scaring people, it's about motivating them to take action and improve their security precisely.

And that's why it's so important for the red team and the organization to work closely together throughout the engagement. Okay, they need to understand the organization's business goals, risk tolerance, and operational constraints in order to design meaningful operational impacts.

It makes sense that you wouldn't want to simulate an attack that would cripple the organization or put their operations at risk. You need to find that balance between demonstrating the impact and avoiding any real world damage exactly.

And that's where the planning phase of a red team engagement is so critical. Okay, it's not just about using the right tools and techniques. It's about understanding the target organization and tailoring the engagement to their specific needs and objectives.

So it's really a customized approach, almost like a tailored suit. Yeah, you're taking into account all the unique factors of that organization, their size, their industry, their risk profile, and designing an engagement that will be both effective and meaningful for them.

Absolutely, and that brings us back to the importance of reporting. Okay, the Red Team report isn't just a list of vulnerabilities. It's a roadmap for improvement. It should tell the story of the attack, highlight key observations, and provide actionable recommendations for strengthening defenses.

So it's almost like a consulting engagement, with the Red Team acting as trusted advisors to help the organization improve their security posture. But I'm curious how do they actually go about writing a report like that. I mean, it can't be as simple as just saying, hey, you guys have some vulnerabilities, you should fix them, right.

It needs to be much more detailed and insightful than that. Okay, one of the things that stood up to me in the book is that they talk about using attack flow diagrams to visually represent the steps taken by the Red Team. I think that would be incredibly helpful for organizations to see exactly how the attack unfolded and what areas need the most attention.

It's like giving them a blueprint of the attack, so they can see exactly where the weak points are and how to fortify them. But what about risk ratings? Do Red Team reports use the traditional high, medium, low scale.

They can, but the book actually proposes an alternative approach that I find much more compelling.

Okay.

Instead of relying on a subjective risk matrix, right, they suggest using metrics based on the red team's goals.

Oh interesting.

Instead of saying this vulnerability has a high likelihood of being exploited, they might say we were able to achieve our goal of stealing sensitive data within twenty four hours. Oh wow. And this approach provides much more actionable information for the organization. It's not just about the euoretical risk of a vulnerability, it's about the demonstrable impact of a successful attack, and it really brings the risks to life.

That's a great point. This all makes perfect sense, but it does raise another question. We've talked a lot about the technical aspects of red teaming, right, but what about the human element? I mean, how do they account for the fact that people are often the weakest link in the security chain.

That's a great question, and it's something that RID teams are very aware of. Remember those social engineering techniques we talked about earlier, Yes, things like phishing, pre texting, and baiting. Red teams use those techniques to test an organization's human defenses.

So they might send a phishing email that looks like it's from the IT department, asking employees to reset their passwords.

Exactly, and they'll track how many employees click on the link, how many enter their credentials, and how far they get before they realize it's a scam. They might also conduct physical security tests, like seeing if they can gain access to secure areas by tailgating employees or maintenance workers.

It sounds like they're really thinking outside the box, looking for any potential weak points in the organization's security. Yeah, and that brings up another question. How do they ensure they don't cause unintended damage? Right? I mean, some of these operational impacts could have serious consequences if they're not carefully controlled.

That's where the concept of deconfliction comes in. It's all about making sure that the Red Team's activities are clearly distinguishable from real world attacks and that everyone is on the same page.

Right.

We'll be back after the break to discuss that and more.

Okay, so we've covered a lot of ground here, but it sounds like we're just getting started. Stay tuned, Welcome back to the deep dive. We're wrapping up our exploration of red teaming, and honestly, my mind is still buzzing from all of this incredible information. We were just talking about the importance of deconfliction, right right, making sure those Red team attacks don't get mistaken for the real deal.

Yeah, it's crucial, especially during those unannounced engagements. Imagine the chaos if this security team saw this suspicious activity and thought it was a genuine threat, you would have like a full blown incidant response for nothing.

Oh, talk about a fire drill gone wrong. So how do they prevent that kind of mix up?

Communication is key? Okay, The Red and Blue teams need to have like clear channels of communication. Okay, maybe predefined contact points, shared logs, or even real time monitoring of the Red team's activities.

So it's like having a referee on hand to make sure everyone's playing by the rules and knows what's going on exactly.

Yeah, and there needs to be a clear process for reporting and verifying anything suspicious. If the Blue team see something that looks like it could be the Red team, they need a way to quickly confirm.

Makes sense, And if it's not the Red team.

Well, then it's game on for a real incident response. But the key is to avoid those false alarms, especially when you're trying to assess how the organization would handle a real attack. But it's not just about deconfliction. Red teams also need to keep meticulous records of everything.

They do, right I imagine, documentation is super important, not just to avoid confusion, but also so the organization can actually learn from the experience.

Absolutely meticulous record keeping is essential for that post engagement analysis. The red team needs to be able to explain exactly what they did, how they did it, and what the organization can learn from it.

It's like leaving a trail of breadcrumbs, but instead of leading to a gingerbread house, it leads to better security.

I love that, and that's where those operator logs come in. The red team should document every single action they take, every command, every file they access, almost like a forensic investigation, but in reverse.

So you can see exactly how they got in, where they went, and what they did once they were inside. It's like a step by step guide to hacking your own organization, but in a good way, of course, precisely.

And those logs are invaluable for the Blue team as they try to understand the attack path and identify areas for improvement.

Absolutely, So, to wrap things up, I think it's safe to say that that red teaming is a critical part of any organization's security strategy. It's not just about finding vulnerabilities. It's about understanding how attackers think, how they operate, and what they're capable of. And it's about using that knowledge to build stronger defenses and protect ourselves from real world threats.

It really is. And the more we understand about how attackers operate, the better equipped will be to defend ourselves.

And have said it better myself, this has been an incredible journey exploring this topic with you for our listeners. If you're interested in learning more about red teaming, we highly recommend checking out the book Red Team Development and Operations. It's a fantastic resource for anyone who wants to understand this increasingly important field of cybersecurity. Well that's all the time we have for today's deep dive. Thanks for joining us on this journey into the world of red teaming.