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Cybersecurity Attacks - Red Team Strategies

Jan 19, 202545 min
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Episode description

This Book is a comprehensive guide to building and managing a red team program within an organization. The text covers essential topics such as defining the mission of a red team, gaining leadership support, building a program from scratch or inheriting an existing one, and managing and assessing the team. It explores the importance of "homefield advantage" and the collaborative approach between red and blue teams. The book provides numerous examples of real-world adversary tactics and techniques, including phishing attacks, credential hunting, and abusing logging and tracing to steal information. The text delves into the use of graph databases and attack graphs to map out the organization's assets and relationships, and it emphasizes the importance of security monitoring and alerting to detect and respond to threats effectively. Finally, the book discusses blue team tactics that red teamers should be familiar with, including centralized monitoring solutions like osquery and the Elasticsearch Stack.

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Transcript

Speaker 1

Welcome back everyone to the deep Dive. This time we're taking a close look at Johann Raeberger's book Cybersecurity Attacks, Red Team Strategies, a.

Speaker 2

Really practical guide for anyone who wants to know about penetration testing and you know, really building a strong security program.

Speaker 1

Definitely. It kind of feels like a masterclass in proactive security almost. Yeah, definitely, showing us how to think like the attackers would, so we can build, you know, a really strong security program exactly.

Speaker 2

And it's all about being prepared and like you said, thinking like an attacker, finding those vulnerabilities, but before the bad.

Speaker 1

Guys do before the bad guys exactly. And it's packed with so many like real world examples and practical advice. It's not just theory.

Speaker 2

Yeah, yeah, absolutely, So let's start.

Speaker 1

The very beginning. Sure, what is red teaming? What's the core idea behind this in cybersecurity?

Speaker 2

Okay?

Speaker 1

So, and how would you explain it?

Speaker 2

I think the easiest way to think about it is, you're basically assembling a team of ethical hackers, okay, whose entire mission is to mimic real world attacks, but from the good side. So they're probing your defenses, your tech, your processes, even like physical security sometimes like a real attacker would Wow.

Speaker 1

So it's really like taking that stressed us to the next level for your entire security setup.

Speaker 2

Yeah, that's a great way to put it.

Speaker 1

Okay, So that kind of begs the question, then, how is this different from something like penetration testing, which we've all heard of?

Speaker 2

Right? So, pin testing is generally more focused. You know, you're zeroing in on a specific system, a specific app to find as weaknesses. Red teaming is more I guess you could say holistic. It's examining how your entire organization responds to a more full blown attack.

Speaker 1

Oh so it's really looking at it from the perspective of not just are there bugs in the software, but how would a human being actually try to get in and exploit those? And then what would happen next.

Speaker 2

Yeah, it's not just about finding like a software bug, it's about how your company reacts when you know things go south.

Speaker 1

It's about their reflexes exactly to security breaches.

Speaker 2

Yeah, and to really test those reflexes, you need a dedicated red team, right.

Speaker 1

Okay, But before you even think about who's on the team, you need to convince the people up top totally.

Speaker 2

Yeah, leadership in is absolutely.

Speaker 1

Critical, Like how do you even begin to get them on board?

Speaker 2

Data? Data is your best friend here? Oh good, show them those scary data breach numbers, like how much they cost?

Speaker 1

Oh, make it real for them.

Speaker 2

Yeah, how much it can impact the bottom line, because that's what they care about.

Speaker 1

They need to see those dollar signs. Yeah, exactly, and be afraid of what's going to happen if they don't invest in security.

Speaker 2

Right. And then once they've signed off, you need to figure out where the Red team fits.

Speaker 1

Okay, where should it fit?

Speaker 2

Ideally a good degree of independence, Okay, reporting directly to like the Blue team, the defenders can actually cause some problems. Oh okay, what because remember the Red team is supposed to be the devil's advocate, you know, right, the weaknesses even if it makes people uncomfortable.

Speaker 1

So they need to be able to operate independently without any pressure from the people they might be embarrassing.

Speaker 2

Exactly, you got.

Speaker 1

Okay, So let's talk about the team itself. Yeah, I mean these are skilled, ethical hackers that we're talking about. Oh yeah, yeah, So how do you even find these people?

Speaker 2

That's the million dollar question, right, attracting and keeping great talent. It's not just about offering a lot of money, although that helps, but you really need to build an environment that speaks to their passion, you know, the thrill of this.

Speaker 1

Okay, well what would that look like?

Speaker 2

So things like development opportunities, you know, go into conferences and just like a culture of sharing knowledge.

Speaker 1

Right, So building this team is more about understanding what motivates them and what gets them excited about cybersecurity than just finding someone who can hack.

Speaker 2

Exactly. You need that mindset, that passion.

Speaker 1

Now, I'm guessing not every hacker out there's going to be ethical, So how do you filter for that?

Speaker 2

That's where you use scenarios in the interview process. Okay, you know, I like to throw out a hypothetical. Ok let's say you got to compromise this HR system to see if someone can pull out data. Would you download your own file, would you access other employee records, or you know, would you propose using dummy data?

Speaker 1

So it's like an ethical puzzle exactly.

Speaker 2

Yeah, and how they answer tells you a lot about their boundaries and how they handle that kind of sensitive information.

Speaker 1

That's super interesting. Yeah, are there any other essential things? To consider when putting this team together.

Speaker 2

I think diversity is absolutely key, Okay, and that's something that the cybersecurity world struggles with in what way? You know it's still a very male dominated field, is it. Yeah, Like globally it's only about eleven percent women.

Speaker 1

Wow, that's a really low number.

Speaker 2

Yeah, it's pretty shocking.

Speaker 1

Why is diversity so important, especially when bailing a red team Because.

Speaker 2

You get more creative and effective solutions when you have different perspectives in the room.

Speaker 1

Oh, you don't want everyone thinking the same way exactly.

Speaker 2

That's a recipe for disaster.

Speaker 1

So you've got your dream team. It's diverse, they're ethical, they're ready to go. Yeah, but then you need to manage them. What's the challenge in managing a red team?

Speaker 2

Well, I think it's about finding that balance, right. You want to give clear goals, but also not squash their creativity, their freedom to explore. Okay, So regular feedback communication is really important building that culture of trust and respect.

Speaker 1

So it's like you're a coach, but you're not dictating every move exactly. You want to make sure that they feel comfortable coming to you and bouncing ideas off of you and not feeling micromanaged.

Speaker 2

Yeah, you got it.

Speaker 1

This is all sounding pretty intense. Are there any other considerations?

Speaker 2

Well, this field can be really prone to burnout in what way? Red teamers are always on edge, you know, right, thinking about new threats and how to get ahead of them. That's a lot of pressure, it is. Yeah, So a healthy team culture, promoting work life balance is essential.

Speaker 1

So really making sure that they can do this job long term and not burn out after a year or two.

Speaker 2

Yeah, you want sustainability, not just a quick burst of energy.

Speaker 1

Okay, so you've got your team, they're happy, they're healthy, they're ready to go. How do they actually plan a test? A Red Team operation?

Speaker 2

It always starts with clearly defined objectives.

Speaker 1

What do you mean?

Speaker 2

What are you trying to achieve? Do you want to disrupt the system? Are you trying to get to some juicy data? Or is it about testing how they respond to an incident?

Speaker 1

Right? So you really need to have a plan. It's not just about breaking.

Speaker 2

Thing, No, definitely not. You get to simulate a real attack, one that actually makes sense for that company.

Speaker 1

Okay, so you've established your target, your goals. What happens next?

Speaker 2

Well, then they got to choose their approach.

Speaker 1

What do you mean by approach?

Speaker 2

Think surgical strike versus carpet bombing.

Speaker 1

I like that analogy.

Speaker 2

Ye know. Surgical strike is very focused, very specific objective, okay. Carpet bombing is more about throwing everything you got seeing what sticks.

Speaker 1

Okay, So how do you know which one's the right way to go?

Speaker 2

It depends. Sometimes you need that precision of a surgical strike to test a very specific mechanism, and other times that broader approach reveals more systemic weaknesses.

Speaker 1

It's about choosing the right tool for the job exactly. Now. Red teams have a real advantage over actual attackers, right because they have that home field advantage.

Speaker 2

Oh yeah, a huge advantage.

Speaker 1

They know the organization inside and out.

Speaker 2

They know the systems, they know the people. They even know the little quirks that nobody documents.

Speaker 1

Right, So they might know about a system that everyone forgot about, or a security protocol that nobody's actually following, or even like a disgruntled employee that they won't be able to manipulate.

Speaker 2

Exactly. All that insider info is gold.

Speaker 1

But what happens is they get caught during an operation.

Speaker 2

It happens, you know, really, and sometimes that can actually be really valuable.

Speaker 1

Oh.

Speaker 2

Interesting, because it's a chance to see how the incident response team, you know, how they react.

Speaker 1

Okay, yeah, it shows their strength and weaknesses.

Speaker 2

Exactly, highlights where they need to improve.

Speaker 1

You can't get that from a theoretical exercise.

Speaker 2

Yeah. The key is to view these as learning opportunities.

Speaker 1

Oh, to embrace those mistakes, right, to make them positive. And this is where we start talking about purple teaming.

Speaker 2

Yeah, purple teaming is all about cloudberation. The red team and the blue team working together, breaking down those silos.

Speaker 1

Instead of working against each other, they're actually joining.

Speaker 2

Forces exactly, sharing knowledge and understanding the threat from both sides.

Speaker 1

How would that actually work.

Speaker 2

They might do joint exercises like threat hunting, where the red team shares what they know about attacker tactics and then the blue team uses that to strengthen their defenses.

Speaker 1

Okay, so it's like they're sparring partners, pushing each other to get better.

Speaker 2

Yeah, that's good analogy.

Speaker 1

Now, how does a red team actually know if what they're doing is working? How do they measure their effectiveness?

Speaker 2

It's a really good question, right, and there are lots of ways to do it. Like what one is just tracking what they find. You know, how many vulnerabilities, how long it takes them to exploit something. Okay, you know, really quantifying.

Speaker 1

The risk so they can go back and say, look, we found all these problems. We help make the organization more secure exactly.

Speaker 2

Yeah, and these reports can be really useful for justifying budgets, yeah, oritizing what needs fixing.

Speaker 1

Oh right, they can say, look, we need more resources to do this because it's actually having a real impact.

Speaker 2

Exactly, you get it.

Speaker 1

So it's not just about the technical side of hacking. It's about communication, analysis and actually making the organization more secure.

Speaker 2

One hundred percent. It's all connected.

Speaker 1

Now, a lot of organizations might be thinking they haven't been attacked, right, so maybe there's nothing to worry about. Maybe they're doing everything right.

Speaker 2

That's a dangerous assumption. Okay, Why because it creates this illusion of control. Oh they think they're secure because they haven't been tested properly.

Speaker 1

Oh so red teaming is almost like forcing them to confront that reality.

Speaker 2

Yeah. It shatters the illusion by exposing those weaknesses so they can fix them before a real attacker gets in.

Speaker 1

It's like a wake up call exactly.

Speaker 2

Prevention is always better than a cure.

Speaker 1

Okay, So let's dive a little deeper into some of the tactics that red teams use. Sure, the book talks about something called attack graphs. What are those?

Speaker 2

Okay? So attack graphs think of it like a roadmap, but for hackers.

Speaker 1

Okay.

Speaker 2

It shows how an attacker might try to move through your systems, So it's.

Speaker 1

Like a blueprint for how they would attack.

Speaker 2

Yeah, it's really valuable for the red team to map out potential paths.

Speaker 1

Oh, to see how different assets connect and where the vulnerabilities.

Speaker 2

Are exactly, you get it.

Speaker 1

And it can be used for threat modeling, vulnerability analysis, even for training your employees on security awareness.

Speaker 2

Yeah, totally. It helps you understand how an attacker thinks.

Speaker 1

Now, the book also mentions threat trees and graphs, Right, how are those different from attack graphs.

Speaker 2

Well, attack graphs focus on those specific paths.

Speaker 1

Okay.

Speaker 2

Threat trees and graphs take a broader look.

Speaker 1

Oh, Okay.

Speaker 2

They map out all the potential threats, what their impact could be.

Speaker 1

So it's like zooming out to see the big picture.

Speaker 2

Exactly, and they often include info about what motivates the attackers, what they're capable of and who they're after.

Speaker 1

Oh wow, so it's not just about the how, but also the why behind an attack.

Speaker 2

Yeah, that's really important.

Speaker 1

That's a crucial distinction, right, because if you understand the why, you can prioritize what to protect and how to defend.

Speaker 2

Absolutely. Yeah.

Speaker 1

Now, the book talks about building these conceptual graphs manually, right, what does that involve? How does it actually work?

Speaker 2

It's basically a brainstorming session. You know, a bunch of security experts getting together, okay, mapping out those scenarios, identifying assets, vulnerabilities, all those attacker actions.

Speaker 1

So you're trying to predict what they might.

Speaker 2

Do exactly, and you can use a whiteboard, sticky notes just trying to connect the dots.

Speaker 1

That sounds super time consuming though.

Speaker 2

It can be, and that's where automation comes in.

Speaker 1

Oh okay, how does that work.

Speaker 2

There are tools that can scan networks, analyze those configurations, find known vulnerabilities.

Speaker 1

So it's like perbocharging that brainstorming session with technology exactly.

Speaker 2

It frees up the security teams from more strategic work.

Speaker 1

Okay, Now, let's shift gears a little bit and talk about measuring how effective a red team's work is sure. The book talks about defining things called metrics and KPIs. What are those? Can you give me some examples of those?

Speaker 2

Yeah? So there are two main times. Ones that focus on the Red team's internal operations, okay, and then ones that look at the impact of their work. Give me an example, like, an operational kpiah could be the number of pen tests they've done. Okay, Well, an impact KPI would be how many critical vulnerabilities they found or how long it takes to fix them.

Speaker 1

Oh so one's about efficiency and the other ones about effectiveness exactly. What about these attack insight dashboards that I saw mentioned in the book?

Speaker 2

Oh yeah, they're really cool.

Speaker 1

What are they?

Speaker 2

Imagine a dashboard that gives you a real time view of what's happening in an operation. Okay, you can see what phase the attack is, in, which assets have been compromised, what techniques are being used.

Speaker 1

So it's like watching the attack unfold live.

Speaker 2

Yeah, super helpful for the Blue team. You know, they can observe what's going on, learn those tactics, and adapt their defenses in real time.

Speaker 1

Like they're getting a front row seat to a real attack exactly. The book also mentioned something called Red Team scores.

Speaker 2

Yeah, what are they? So they basically quant to find the impact of the findings. Oh, they might assign points based on how bad a vulnerability is, how easy it is to exploit it, and how what do you damage it could do.

Speaker 1

So it helps prioritize what to fix first exactly.

Speaker 2

You want to focus on the things that pose the biggest risk, right okay.

Speaker 1

And then I saw burn down charts. Yeah, what are those used for?

Speaker 2

They're like visual trackers Okay. In this case, they show you how quickly vulnerabilities are being addressed.

Speaker 1

Oh, so you can see if the organization is actually fixing the problems that the Red Team finds, right exactly. And then there's this blast radius visualization. Yeah, what's that and why is it important?

Speaker 2

Well, it shows you the potential fallout if an attack is successful. Okay, Like let's say the Red Team got hold of a user account. Okay, this visualization would show you all the systems they could access, the data they could get to.

Speaker 1

Oh wow, it's like a worst case scenario map.

Speaker 2

Yeah, you can see the potential domino effect.

Speaker 1

That's important for risk management because then you can really understand what's at stake.

Speaker 2

Absolutely.

Speaker 1

Now, one thing the book points out is that using simple ratings like critical, high, medium, low to assess risk isn't really enough.

Speaker 2

Yeah, those terms can be subjective.

Speaker 1

Oh okay.

Speaker 2

What one person thinks is critical, another person might say is high. And without clear definitions, it's hard to prioritize you know where to put your resources.

Speaker 1

So how do you move beyond those simple ratings?

Speaker 2

Then? Well, you could use more quantitative methods like simulations. Oh okay, like Monty Carlo simulations.

Speaker 1

Money Carlos simulations.

Speaker 2

That sounds complex, It can be, but it's a powerful tool. You basically run thousands of simulations to model different attack scenarios and then calculate the impact of each one.

Speaker 1

So you're factoring the likelihood of the attack, how strong your defenses are, and what the financial hit would be.

Speaker 2

Yeah, exactly. You want to make data driven decisions, not just gut feeling, right, Data is key, okay.

Speaker 1

The book also mentions meantime metrics. Yeah, what are those?

Speaker 2

So these basically measure how long it takes to do certain things, how long to detect an attack, how long to fix a vulnerability, how long to recover.

Speaker 1

So you're measuring how quickly you can respond and then using that to improve your response times.

Speaker 2

Yeah, you want to be fast and efficient.

Speaker 1

Right, Okay. There's also something called the Threat Response Matrix, right, can you explain what that is?

Speaker 2

Basically, it's a playbook, Okay. It lists potential threats, what their impact could be, and how the organization wants to respond.

Speaker 1

Oh, so everybody knows what to do if a specific threat shows up exactly.

Speaker 2

Yeah, especially when you're under pressure, you need a plan.

Speaker 1

Right.

Speaker 2

Then there's the Test Maturity Model Integration or TMI.

Speaker 1

TMI Okay, I'm not familiar with that.

Speaker 2

It's a framework for evaluating how mature a testing process is. Okay. It wasn't designed specifically for security, okay, but a lot of the principles apply to red teaming.

Speaker 1

Okay, So how can organizations use this framework to improve their red teaming?

Speaker 2

Well, they can assess their processes against the TMMI and see where they need to improve.

Speaker 1

So it's like benchmarking themselves against best practices.

Speaker 2

Exactly. You want to make sure your operations are top notch.

Speaker 1

Okay, I'm sure our listeners are eager to hear about some of the more I guess cutting edge red team operations. Oh yeah, definitely, let's dive into those more innovative and challenging exercises.

Speaker 2

Okay, let's start with progressive red teaming, which really pushes beyond those traditional methods.

Speaker 1

Okay.

Speaker 2

One example is cryptocurrency mining, oh wow, where red teams are simulating attacks designed to basically hijack your computing resources to make money.

Speaker 1

So instead of stealing data, they're stealing your processing power.

Speaker 2

Yeah, exactly, they're using your resources for their own profit.

Speaker 1

That's a big concern for organizations today.

Speaker 2

It is. Yeah, it can be really expensive, slow down your systems, even damage your hardware.

Speaker 1

What are some other types of progressive red teaming operations?

Speaker 2

Another area is red teaming for privacy violations. Okay, so you're testing the defenses against attacks that are trying to steal or misuse personal data.

Speaker 1

So basically making sure you're complying with things like GDPR.

Speaker 2

Exactly. They might simulate attacks that exploit weaknesses in data protection.

Speaker 1

So you might find out that your web app is insecure or your database isn't configured properly.

Speaker 2

Yeah, exactly. You're finding those hidden risks that companies might not even be aware of.

Speaker 1

It's all about being proactive, right, finding the problem before it becomes a bigger problem.

Speaker 2

Yeah. Absolutely.

Speaker 1

Are there any other progressive red team exercises that you think are worth mentioning?

Speaker 2

Yeah? Another big one is attacking AI and machine learning systems.

Speaker 1

Oh interesting.

Speaker 2

So these are systems that are becoming more and more common, right, and we're starting to see the vulnerabilities in them.

Speaker 1

What kind of vulnerabilities?

Speaker 2

Well, one example is what's called data poisoning. Okay, Attackers try to manipulate the data that's used to train the AI models, so.

Speaker 1

Like introducing biases or errors that make the AI make bad decisions.

Speaker 2

Yeah, exactly, And it can be really hard.

Speaker 1

To detect, right, because you're not breaking into a system, You're just manipulating the data that the.

Speaker 2

System uses, right, You're tricking the AI.

Speaker 1

Wow. Wow, that's a whole new level of complexity, it is.

Speaker 2

Yeah.

Speaker 1

What other AI related attacks are red teams simulating?

Speaker 2

There's also something called adversarial machine learning, where they create inputs that are designed to fool the AI models, make them misclassified data.

Speaker 1

So it's like an optical illusion for AI.

Speaker 2

Yeah, that's a great way to put it.

Speaker 1

They can bypass security, manipulate markets, even control physical systems exactly.

Speaker 2

It's a serious concern.

Speaker 1

So what can organizations do to protect themselves from this?

Speaker 2

Well, it's a constantly evolving area, right, But some things they can do are implement robust data validation okay, develop more resilient models, and just stay up to date on the latest threats.

Speaker 1

So red teaming is crucial here too, right, because they can help you understand the weaknesses in your AI system.

Speaker 2

Oh absolutely, They're essential for staying ahead of the curve in this area.

Speaker 1

Okay. Any other innovative exercises.

Speaker 2

Yeah, there's one called operation Vigilanting Operation vigilante, okay, where the red team goes beyond just finding vulnerabilities Okay, they actually fix them.

Speaker 1

Wait, so they're not just pointing out the problems, they're actually solving them exactly.

Speaker 2

They're taking more proactive approach.

Speaker 1

That blurs the line between red teaming and being like a system administrator.

Speaker 2

It does, yeah, but it can be a really effective way to address vulnerabilities quickly.

Speaker 1

So it's good for organizations that are maybe struggling to keep up with patching and fixing things. Yeah, exactly, But how do you make sure the blue team knows what's going on?

Speaker 2

Transparency is key. The red team has to document everything. Okay, share that info with the Blue team so they can update their defenses.

Speaker 1

So everybody's in the loop exactly, no surprises. Okay. Now let's talk about situational awareness and knowledge graphs. Sure, what are those and how are they important for red teaming?

Speaker 2

Well, a knowledge graph think of it like a map, okay, but for your organization's cybersecurity.

Speaker 1

Okay.

Speaker 2

It shows you the relationships between different assets, users, vulnerabilities.

Speaker 1

So it's like a Google Maps for your secure scurity.

Speaker 2

Yeah, that's a great way to put it.

Speaker 1

And the Red team can use that to find potential attack paths exactly. It's super helpful for THREP modeling, vulnerability analysis, responding to incidents.

Speaker 2

Yeah. It's can to be more and more important as a tax get more sophisticated.

Speaker 1

Okay, So how do you actually create these knowledge graphs.

Speaker 2

You can do it manually, but it takes forever and it's not always accurate. Right, So the book talks about using something called graph databases like Neo four J.

Speaker 1

Neo four J. What's that.

Speaker 2

It's a database that's specifically designed to store and query graph data. Okay, it's really good at handling complex relationships. Oh, okay, create nodes that represent things like users, systems, vulnerabilities, and then you connect them with relationships that define how they're connected.

Speaker 1

So you're building this virtual map of how everything is interconnected exactly.

Speaker 2

And because of the database, you can ask questions like what systems can this user access okay, or what vulnerabilities are on this system and NEO four J can answer that instantly. That's powerful, it is.

Speaker 1

Yeah, So how does this help the Red team?

Speaker 2

It helps them plan and execute attacks more effectively. They can find systems with sensitive data or systems that are vulnerable to specific.

Speaker 1

Attacks, so they can prioritize their targets exactly.

Speaker 2

Yeah.

Speaker 1

What about the Blue team? Does this help them too?

Speaker 2

Definitely? It helps them detect threats okay, by identifying unusual user activity or system behavior that could indicate an attack.

Speaker 1

So they're using it to find anomalies.

Speaker 2

Yeah, exactly.

Speaker 1

It sounds like knowledge graphs are a game changer for both sides.

Speaker 2

They really are.

Speaker 1

We talked about how they can show relationships between assets, users, but what about vulnerabilities. How do those fit into this model?

Speaker 2

Vulnerabilities are nodes too, just like users and systems. Okay, you connect them to system nodes to show which systems are affected.

Speaker 1

So like, you could have a node for a buffer overflow vulnerability and connect that to all the systems running software that's vulnerable to.

Speaker 2

That exactly, then you can quickly see which systems are at the highest risk.

Speaker 1

Okay, that makes sense. Yeah, Now let's talk about something called credential hunting. What are some of the techniques that red teams use to find those sensitive credentials within an organization?

Speaker 2

So, credential hunting is all about finding the keys to the kingdom, right, those passwords, those access tokens that unlock everything.

Speaker 1

Right, like the ultimate goal of a hacker exactly. So how do they do it?

Speaker 2

Well, let's start with a simple one. Searching for common patterns.

Speaker 1

What do you mean by that?

Speaker 2

Literally searching for passwords that might be stored in plain text. People do that more often than you think. Yeah. Really, They look through configuration files, source codes, scripts, documents anywhere that might have passwords. Wow. They search for keywords like passwords, secret, API key.

Speaker 1

It sounds so simple, but it works.

Speaker 2

It does, yees, especially when people don't follow good security practices.

Speaker 1

Okay, now there are more sophisticated techniques, right, Oh, yeah, of course, what else can they do?

Speaker 2

On One is to use indexing.

Speaker 1

Indexing, Yeah, you.

Speaker 2

Know how operating systems and applications index things to make searches faster. Well, red teams can use that to their advantage. Okay, how they can query the index and search for keywords like password across all the files.

Speaker 1

So they're using the system's own tools against itself exactly. So if you're on Windows, for example, what would they use.

Speaker 2

They could use PowerShell to query the Windows Search index oct and find anything that has the word password in it.

Speaker 1

What about on mac OS and Linux?

Speaker 2

Oh, they have tools too. macOS has Spotlight, which indexes files, and Linux has rep and find.

Speaker 1

So no matter what system you're on, they can find those hidden credentials pretty much.

Speaker 2

Yeah.

Speaker 1

Now you can get even more specific, right, Oh yeah, what about techniques that target particular applications or systems?

Speaker 2

Right? So one example is analyzing process.

Speaker 1

Memory process memory.

Speaker 2

Yeah, when an application is running, its code and data are loaded into memory. Okay, and that memory can contain things like passwords, API keys, encryption keys.

Speaker 1

Oh wow, so they're looking for the stuff that's actually in use exactly.

Speaker 2

They can dump the memory and then search through it for credentials.

Speaker 1

It's bypassing all the usual security stuff like file encryption.

Speaker 2

Yeah, it's a powerful technique because they're getting the data in its most vulnerable state. Wow. Okay, And there are other memory based techniques too, like what they can abuse logging mechanisms.

Speaker 1

How does that work?

Speaker 2

Well? Applications and systems often keep logs of what they're.

Speaker 1

Doing, right, for debugging or auditing.

Speaker 2

Yeah, but those logs can sometimes contain sensitive information oh okay, like passwords or encryption keys. So red teams can manipulate these logs to capture that data.

Speaker 1

So they're turning logging, which is supposed to be a security feature, into a vulnerability exactly.

Speaker 2

They're turning the system against itself.

Speaker 1

Are there any examples of this on Windows?

Speaker 2

Yeah, there's something called event tracing for Windows or etw Okay, developers create detailed logs, okay, but red teams can sometimes hijack those logs and get passwords and encryption keys.

Speaker 1

Wow. That's sneaky, it is. Yeah, it sounds like red teams need to be incredibly creative.

Speaker 2

Oh yeah, definitely, thinking outside the box's key.

Speaker 1

Okay. Now, what about spoofing credential prompts? Is that something they do.

Speaker 2

Oh yeah, that's a classic.

Speaker 1

How does that work?

Speaker 2

They create fake login windows that look just like the real ones? Oh wow, So the user thinks they're entering their password into a legitimate.

Speaker 1

System, but they're actually giving it to the attacker exactly. And how do they deliver these fake prompts.

Speaker 2

They might use phishing emails or malicious websites.

Speaker 1

Oh so they're relying on people clicking on things they shouldn't.

Speaker 2

Yeah, social engineering is a big part of it.

Speaker 1

So even a security conscious person might fall for.

Speaker 2

This absolutely if it's done well, it can be very convincing. That's a little scary, Yeah it is. But there are things you can do to protect yourself. What always double check the url of any website that asks for your password.

Speaker 1

Okay, yeah, make sure it's the real site.

Speaker 2

Yeah. Wary of any unexpected prompts for your password.

Speaker 1

Okay, good advice.

Speaker 2

Yeah.

Speaker 1

Now the book also mentions password spring.

Speaker 2

Right, what's that? So it's a way to bypass a lot of those brute force protections. Instead of trying a ton of passwords against one account, Okay, they try a few common passwords against a lot of accounts.

Speaker 1

So it's like they're casting a wider net hoping to catch those users who have weak passwords.

Speaker 2

Exactly. Yeah, they might use a list of the top one hundred most common passwords and try those against thousands of accounts.

Speaker 1

Oh so, because they're only trying a few passwords per account, right, it's less likely to trigger any alarms.

Speaker 2

Exactly, it flies under the radar.

Speaker 1

Clever it is.

Speaker 2

Yeah, but there's a good defense against this. What's that multi factor authentication?

Speaker 1

Oh right, that extra layer of security.

Speaker 2

Yeah, even if they get the password, they still need that second factor.

Speaker 1

Okay, that makes sense.

Speaker 2

Yeah.

Speaker 1

Now we've talked a lot about the offensive side of red teaming, right, but the book also talks about protecting the red team themselves.

Speaker 2

Yes, that's really important.

Speaker 1

Why is that so important? I mean, there are the attackers. Shouldn't they be able to protect themselves.

Speaker 2

Well, they can become targets too, really, Yeah, they have access to sensitive information, they use powerful tools, so other attackers might try to go after them.

Speaker 1

So they're like high value targets in the cybersecurity world.

Speaker 2

Exactly. Yeah, so protecting them should be a top priority.

Speaker 1

So what can you actually do to protect them?

Speaker 2

It starts with the basics, you know, securing their machines.

Speaker 1

Okay, so strong passwords, firewalls, all that good stuff.

Speaker 2

Yeah, all the things we tell everyone else to do. They need to do it too, right, and.

Speaker 1

They shouldn't be using those machines for personal stuff.

Speaker 2

Definitely not, that's just asking for trouble.

Speaker 1

The book also mentions improving documentation. Right, why is that important for security?

Speaker 2

Well, it helps them keep track of what they're doing. Oh, they can share information with each other, and it provides evidence of their findings. So it's like an audit trail exactly, and it can protect them if anyone ever questions their actions.

Speaker 1

Oh right, it's like proof of what they did and why they did it exactly. And one way to improve documentation is to customize those shell prompts.

Speaker 2

Yeah, that's a good one.

Speaker 1

Can you explain what that is for people who might not know.

Speaker 2

So the shell prompt is that text you see on the command line right where you type in commands. Okay. Red teamers can customize it to include things like the date, the time, the username, the host name, the directory they're in.

Speaker 1

So it's automatically adding all this information to their commands.

Speaker 2

Yeah. Basically, so if.

Speaker 1

Someone needs to review their actions, it's all right there exactly.

Speaker 2

It's like a built in log Okay.

Speaker 1

What other tips does the book give for protecting the Red team?

Speaker 2

Well, monitoring log in attempts is a big one.

Speaker 1

Okay. So if someone tries to log into their machine, they'll get alerted exactly.

Speaker 2

Yeah, especially if it's from a weird location or at a strange time.

Speaker 1

It's like a trip wire.

Speaker 2

Yeah, you got it now.

Speaker 1

I found it interesting that the book encourages Red teams to learn from the Blue team.

Speaker 2

Oh yeah, absolutely.

Speaker 1

Why is that? Well?

Speaker 2

Red teams and Blue teams often have very different perspectives.

Speaker 1

Right, one's attacking, one's defending.

Speaker 2

Exactly, but they can learn a lot from each other.

Speaker 1

So breaking down those silos can actually make both sides stronger.

Speaker 2

Definitely. Red teams can learn from the tools and strategies that blue teams use.

Speaker 1

Oh okay, how does that help them?

Speaker 2

Well, for example, blue teams use something called centralized monitoring solutions.

Speaker 1

Okay.

Speaker 2

These collect security data from all over the organization.

Speaker 1

Okay, so instead of looking at logs on individual machines, you have everything in one place.

Speaker 2

Exactly. It gives you a bird's eye view.

Speaker 1

Okay, So how does this benefit the Red team.

Speaker 2

Well, if they understand how these systems work, okay, they can design attacks that are more likely to go undetected.

Speaker 1

So it's like knowing how the enemy thinks, so you can outsmart them.

Speaker 2

Yeah, exactly, it's all about strategy.

Speaker 1

What are some specific tools that the book recommends red teams should learn.

Speaker 2

Two big ones are Oscary and the Elastic Search Stack.

Speaker 1

Okay, let's start with Oscary. What is that?

Speaker 2

So? Oscary is really cool?

Speaker 1

Okay.

Speaker 2

It lets you query your operating system like it's a database.

Speaker 1

Oh, interesting, and get.

Speaker 2

All sorts of information like running processes, network connections, user accounts, hardware details.

Speaker 1

So it's like having this super powerful search engine for your computer.

Speaker 2

Yeah, that's a great way to put it.

Speaker 1

How would a red team use it?

Speaker 2

Well, they can use it for reconnaissance, uh, you know, gathering information about the target system. But they can also use it after they've compromised a system, oh, to dig deeper and find new targets.

Speaker 1

So it's useful at multiple stages of an attack.

Speaker 2

Exactly, it's a versatile tool.

Speaker 1

Okay. What about the Elastic Search Stack.

Speaker 2

So, elastic search is a set of open source tools for working with data. Okay, it's used a lot by Blue teams for log management, security monitoring, threat hunting.

Speaker 1

So it's about making sense of all that data.

Speaker 2

Yeah, exactly. Security generates tons of data, and elastic search helps you make sense of it.

Speaker 1

Okay, So how can Red teams benefit from understanding elastic search.

Speaker 2

Well, if they know how Blue teams use it to detect attacks, Okay, they can figure out ways to avoid detection.

Speaker 1

So it's like learning the enemy's playbook exactly.

Speaker 2

You got to know their moves to counter them.

Speaker 1

Now, let's move on to something I find really interesting. Sure, traps, deceptions, and honey pots.

Speaker 2

Oh yeah, those are fun.

Speaker 1

They're all about deception.

Speaker 2

Right exactly, you're trying to trick the attackers into revealing themselves.

Speaker 1

Okay, can you give me some concrete example.

Speaker 2

Sure, So a honeypot file okay, is basically a fake file that looks like it has valuable.

Speaker 1

Information okay, like passwords or financial data.

Speaker 2

Yeah, something that an attacker would be interested in, right, and you place it somewhere they're likely to look.

Speaker 1

So it's like bait.

Speaker 2

Exactly, And when they take the bait and open the file, it triggers an alert.

Speaker 1

Oh so you know someone snooping around exactly.

Speaker 2

Yeah.

Speaker 1

No. What about traps? Are they different from honeypot files?

Speaker 2

Yeah, traps are more active. They might be scripts or programs that execute when an attacker does something specific, so.

Speaker 1

Like trying to access a certain file.

Speaker 2

Yeah exactly, it's like a trip wire okay, And when the trap is triggered, it logs what they did, maybe even blocks their access.

Speaker 1

So it's not just detecting them, it's actually doing something to.

Speaker 2

Stop them, right, it's more defensive.

Speaker 1

What about deceptions, how do those work?

Speaker 2

Well? You create fake assets that look real okay, like a decoy web server, a fake database, even a made up user account.

Speaker 1

So you're trying to distract them, lead them down the wrong path exactly.

Speaker 2

You want to waste their time and get them away from the real stuff.

Speaker 1

So once you've set up these traps and honeypots and everything, how do you actually monitor them?

Speaker 2

Well, operating systems have arditing features okay, what are those? They track certain events like file access, process creation, network connections.

Speaker 1

Okay.

Speaker 2

You can use these features to watch the decoys and see if anyone interacts with them.

Speaker 1

So you're looking for any signs that someone is touching something. They shouldn't.

Speaker 2

Exactly, you're looking for those red flags on Windows?

Speaker 1

How would you do that?

Speaker 2

You can use the security audit policy okay, and set it to track specific events, so if someone tries to open a honeypot file, you'll see it in the logs.

Speaker 1

What about on other systems like mac os and Linux?

Speaker 2

They have similar features. Mac Os has audit policies okay, and Linux has audit So no.

Speaker 1

Matter what system you're using, you can monitor these decoys.

Speaker 2

Yeah you can.

Speaker 1

Are there any tools that can help with this?

Speaker 2

Oh yeah, tons of them. They are open source tools, commercial tools, things like the Elastic Search Stack, Splunk Oscary, so.

Speaker 1

They can analyze all those logs and alert you if something suspicious happen.

Speaker 2

Exactly. They make your life a lot easier.

Speaker 1

So you've set up your honeypot file, you're monitoring it. How do you actually get alerted if someone tries to open it?

Speaker 2

Well, the good old fashioned email is still reliable, okay. Most people check their email regularly. It's a simple way to send notifications.

Speaker 1

But there are other ways too, right.

Speaker 2

Oh yeah, you can use desktop notifications okay, those pop up messages you see on your screen, they're hard to mess there's a little alarm going on, exactly. Yeah.

Speaker 1

You can also tie those alerts into something called SIME systems.

Speaker 2

Right. What are so SIM stands for Security Information and Event Management.

Speaker 1

Okay.

Speaker 2

They're systems that collect and analyze security data from all over the place. Okay, and they can trigger automated responses. Oh.

Speaker 1

Interesting.

Speaker 2

So let's say someone accesses your honeypot file, the SIGN system could automatically block their IP address.

Speaker 1

Oh wow, that's impressive.

Speaker 2

Yeah, it's really powerful for containing attacks quickly.

Speaker 1

It's like having a digital security guard that reacts instantly.

Speaker 2

Yeah, that's a good analogy.

Speaker 1

Now, we talked about how red teams can learn from blue teams by understanding those centralized monitoring solutions. Can you give me some more specifics on how that helps them be more effective?

Speaker 2

Sure? So, one thing they can learn is how to blend in with normal network traffic.

Speaker 1

Okay.

Speaker 2

They can make their attacks look less suspicious so they don't stand out. Exactly. They can also learn how to modify law files oh wow, to cover.

Speaker 1

Their tracks so it's like they are never there.

Speaker 2

Right, And they can even find ways to exploit weaknesses in those monitoring tools.

Speaker 1

It's like turning the tables.

Speaker 2

Yeah, it's all about knowing how the other side thinks.

Speaker 1

Now, could Red teams actually use those same tools that blue teams use to protect their own infrastructure?

Speaker 2

Absolutely, they can, really. Yeah. They might use oscary to monitor their own systems okay, to make sure nobody's trying to attack them, right, And they might use elastic search to analyze their own logs.

Speaker 1

So it's like using the enemy's weapons against them.

Speaker 2

Yeah, in a way.

Speaker 1

But it also shows that both teams are really working towards the same goal exactly.

Speaker 2

They both want to improve security.

Speaker 1

Okay. Now we focus a lot on the technical side, right, but the book also emphasizes the human element.

Speaker 2

Yeah, that's crucial.

Speaker 1

What are some of the things to consider when it comes to the people involved in red teaming?

Speaker 2

Well, the Red team needs to be aware of the impact their actions can have other people targeting.

Speaker 1

Okay, what do you mean.

Speaker 2

These exercises can be stressful, you know, right, so falls for a phishing attack, they might feel.

Speaker 1

Embarrassed, right, they might feel like they failed.

Speaker 2

Exactly, So it's important to do these exercises in a way that minimizes that negative impact.

Speaker 1

So be sensitive and provide support afterwards.

Speaker 2

Yeah, exactly. You want to help people learn from the experience.

Speaker 1

Okay. Now what about the Red Team members themselves?

Speaker 2

Right, So they're also vulnerable. They're under pressure, they handle sensitive information, they use powerful.

Speaker 1

Tools, so they could be targeted by attackers.

Speaker 2

Absolutely, they could be victims of social engineering, phishing, even blackmail.

Speaker 1

So you need to protect them too.

Speaker 2

Exactly how do you do that? Security awareness training is really important, Okay. They need to know how to spot and avoid those threats.

Speaker 1

So training that's tailored to the risks they face.

Speaker 2

Yeah, exactly.

Speaker 1

What else can you do?

Speaker 2

Give them ways to report suspicious activity okay, and to seek help if they need it.

Speaker 1

So it's about creating a culture of security that includes the Red Team exactly.

Speaker 2

They need to feel supported.

Speaker 1

Now, one of the biggest challenges in cybersecurity is staying ahead of the curve.

Speaker 2

Oh yeah, definitely.

Speaker 1

How can Red Teams keep up with all the new threats and vulnerabilities?

Speaker 2

Well, one way is to be active in the security community. Okay, you know, go to conferences, read blogs, participate in online forums. So learn from other people exactly, and share your own knowledge too.

Speaker 1

Right, it's a two way street, it is. Yeah, what else can they do?

Speaker 2

They need to develop their own tools and techniques.

Speaker 1

Okay. Why is that so important?

Speaker 2

Because the attacks are always changing, right, If you just rely on the existing tools, you'll be fall behind.

Speaker 1

So you need to be innovative exactly.

Speaker 2

You need to think like an attacker.

Speaker 1

Now that sounds really challenging.

Speaker 2

It is, yeah, but it's also really rewarding.

Speaker 1

What kind of skills do you need to be a good RED tumor.

Speaker 2

Well, obviously you need strong technical skills okay, like what understanding operating systems, networks, programming, But you also need creativity and problem solving skills.

Speaker 1

You need to be able to think outside the box exactly.

Speaker 2

You need to see things that other people miss.

Speaker 1

And I imagine teamwork is important too.

Speaker 2

Oh yeah, crucial. You can't do this alone.

Speaker 1

You need to be able to communicate, share knowledge, learn from each other.

Speaker 2

Absolutely. Yeah.

Speaker 1

Now, one specific area that RED teams often target is active directory. Right, what is that and why is it such a popular target? So?

Speaker 2

Active directory is MICROSOFTS Directory service for Windows networks.

Speaker 1

Okay.

Speaker 2

It's basically a database that stores info about users, computers, other resources. Okay, and it handles authentication and authorization, so it controls who has access.

Speaker 1

To what it's like the central nervous system of the network.

Speaker 2

Yeah, that's a great way to put it.

Speaker 1

And if you control active directory, you control.

Speaker 2

Everything pretty much. Yeah.

Speaker 1

So what are some of the tactics that red teams use to attack it?

Speaker 2

One common one is credential dumping okay. They use tools to extract passwords from the database okay, and they also try to exploit vulnerabilities in the services that act to directory uses, like herberos.

Speaker 1

So they're finding ways to bypass the security exactly.

Speaker 2

They're looking for weaknesses.

Speaker 1

Another tactic you mentioned is privilege escalation. What's that?

Speaker 2

So that's where they try to gain higher levels of access Okay. They might start with a regular user account okay, but they use various techniques to try to get administrator privileges.

Speaker 1

So they're working their way up the ladder exactly.

Speaker 2

Yeah, and once they're an administrator, they can do pretty much anything.

Speaker 1

That's scary, yeah it is. So what can organizations do to protect their active directory?

Speaker 2

Strong passwords, multi factor authentication, keep everything.

Speaker 1

Patched, the usual stuff.

Speaker 2

Yeah, it's basic but important.

Speaker 1

Right.

Speaker 2

They can also segment their network okay, so if one part gets compromised, it doesn't affect the whole thing.

Speaker 1

So it's about limiting the damage exactly. Now a lot of organizations are moving to the cloud.

Speaker 2

Yeah, that's a big trend.

Speaker 1

What are some of the unique challenges for RED teams when it comes to cloud security.

Speaker 2

Well, one big difference is the shared responsibility model. Okay, the cloud provider is responsible for some things and the customer is responsible for others.

Speaker 1

So it's a partnership.

Speaker 2

Yeah, but it can get.

Speaker 1

Confusing, right, who's in charge of what?

Speaker 2

Exactly? So RED teams need to understand that to test things properly.

Speaker 1

It's like sharing an apartment. You need to know who's supposed to clean what.

Speaker 2

Yeah, that's a good analogy.

Speaker 1

What other challenges are there?

Speaker 2

Well, cloud environments are constantly changing. Resources can be created and deleted very quickly.

Speaker 1

Oh wow, so it's like trying to hit a moving target exactly.

Speaker 2

Yeah. RED teams need to adapt their tools and techniques.

Speaker 1

What are some of the tools they use.

Speaker 2

Well, one important one is Cloud Security Posture Management or CSPM.

Speaker 1

Okay, what's that.

Speaker 2

It's a tool that helps organizations assess their cloud security.

Speaker 1

Okay.

Speaker 2

It looks for misconfigurations and vulnerabilities.

Speaker 1

So it's like an automated security check.

Speaker 2

Yeah, that's a good way to think about it and.

Speaker 1

How to red team use it.

Speaker 2

They use it to find weaknesses okay, and then they design at tax that exploit those weaknesses.

Speaker 1

So they're finding the cracks in the armor exactly.

Speaker 2

They're looking for the easy ways in.

Speaker 1

What other techniques do they use, Well, there's cloud penetration testing.

Speaker 2

It's like regular penetration testing, right, but specifically for cloud environments.

Speaker 1

Okay, but the cloud is so different you must need special skills for that.

Speaker 2

Oh yeah, definitely, you need to understand things like serverleist, computing, containerization, micro services.

Speaker 1

There's a whole different set of technologies it is. Yeah, Now, I know this field is always changing, right, What are some of the emerging trends in red teaming that we should keep an eye on.

Speaker 2

Well, one big one is automation, Okay. Red teams are automating more and more tasks.

Speaker 1

So they can do more in less time.

Speaker 2

Exactly. They can scan for vulnerabilities faster, develop exploits quicker.

Speaker 1

So it's all about efficiency.

Speaker 2

Yeah. Basically, thread intelligence is becoming more important okay. Red teams are using it to make their attacks more realistic.

Speaker 1

Okay, so they're tailoring their attacks to mimic real world threats.

Speaker 2

Exactly.

Speaker 1

Yeah, they're learning from what the bad guys are actually.

Speaker 2

Doing, right, that makes their exercises more valuable.

Speaker 1

Okay, any other trends.

Speaker 2

Artificial intelligence is starting to play a role, Oh wow, really Yeah, it's early days, okay, but Red teams are using AI to automate tasks, analyze data, even create new attacks.

Speaker 1

So it's like AI is becoming a tool for both the attackers and the defenders.

Speaker 2

Exactly. Yeah, it's going to change the game. What else, attack surface management is becoming a bigger focus.

Speaker 1

What's that.

Speaker 2

It's about reducing the number of ways that an attacker can get in Okay. Red teams can help organizations identify those weaknesses and prioritize them.

Speaker 1

So it's about being proactive, not just waiting for an attack to happen.

Speaker 2

Exactly. Yeah. And finally, purple teaming is gaining more traction.

Speaker 1

Right where the Red team and Blue team work together.

Speaker 2

Yeah, they share knowledge, they learn from each other.

Speaker 1

So it's a more collaborative approach to security.

Speaker 2

Exactly. It's about breaking down those silos and working as a team.

Speaker 1

That makes a lot of sense. Yeah, Now, This has been a really fascinating discussion.

Speaker 2

Thanks.

Speaker 1

I'm sure our listeners have learned a lot, I hope so. But for someone who might be new to all this, what's the one key takeaway they should remember?

Speaker 2

Security is a journey, not a destination. Okay, there's no such thing as perfect security. It's about constantly evaluating your risks, finding your weaknesses, and improving your defenses.

Speaker 1

So it's about being proactive exactly.

Speaker 2

Yeah, always be one step ahead.

Speaker 1

It's a continuous process of improvement.

Speaker 2

Yeah, and red teaming is a big part of that.

Speaker 1

Now, what about organizations that are thinking, Okay, this all sounds great, but we can't afford a dedicated red team.

Speaker 2

You don't necessarily need a full blown team to get started.

Speaker 1

Okay, what would you recommend them start.

Speaker 2

By just thinking like a red teamer?

Speaker 1

How do you do that?

Speaker 2

Look at your own security with a critical eye, ask yourself those tough questions like what what are the things you really need to protect? Okay, how would someone try to attack you? Where are the weak spots in your defenses?

Speaker 1

So put yourself in the attacker shoes.

Speaker 2

Exactly, see things from their perspective.

Speaker 1

You don't need fancy tools.

Speaker 2

For that right, not at all. There are free tools out there, open source scanners, penetration testing tools.

Speaker 1

She can get started without spending a lot of money.

Speaker 2

Yeah, you do. Stay informed, that's huge, Okay. Read security blogs, go to webinars, follow the.

Speaker 1

Experts, keep up with the latest threats.

Speaker 2

Exactly. Knowledge is power.

Speaker 1

So it's about continuous learning.

Speaker 2

Yeah, always be learning.

Speaker 1

This has been a really insightful conversation. Have Yeah, I'm sure our listeners have a lot to think about, hopefully, but before we go, what's the one thing you'd like them to remember? The most important takeaway from the book.

Speaker 2

Red Teaming is so much more than just hacking. It's about challenging those assumptions, finding those hidden weaknesses, and always pushing the boundaries of security.

Speaker 1

So it's about being proactive and staying ahead.

Speaker 2

Absolutely.

Speaker 1

Johann Reeberger's book Cybersecurity Attacks, Red Team Strategies is a fantastic guide for anyone who wants to build a strong security program.

Speaker 2

Yeah, so must read.

Speaker 1

Thanks for joining us on this deep dive.

Speaker 2

It was my pleasure and.

Speaker 1

For our listeners, remember, think like an attacker, but defend like a pro.

Speaker 2

Couldn't have said it better myself.

Speaker 1

Until next time, stay curious, and keep exploring

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