Speaker 1: Welcome to our deep dive into rede We've got a
Speaker 1: stack of insights just straight from the source tribe of hackers,
Speaker 1: Red Team. It's packed with advice from top offensive security experts,
Speaker 1: and we're here to break it all down for you.
Speaker 2: Yeah, we're going to be going beyond the usual penetration
Speaker 2: testing today and really getting into how red teams emulate
Speaker 2: real world adversaries. By the end of this you'll have
Speaker 2: a solid grasp on how Red teamers think, the diverse
Speaker 2: skills they bring to the table, and their unique approach
Speaker 2: to problem solving.
Speaker 1: So it's like getting a sneak peek into the minds
Speaker 1: of the pros it is. But before we jump into
Speaker 1: all that, let's start with the basics. What exactly is
Speaker 1: red teaming. I feel like the term gets thrown around
Speaker 1: a lot, but is there like a single agreed upon definition.
Speaker 2: It's interesting, isn't it. The lack of one hard and
Speaker 2: fast definition actually reflects how dynamic cybersecurity is. Threats are
Speaker 2: constantly changing, so red teaming has to adapt.
Speaker 1: To makes sense.
Speaker 2: But at its core, it's about pushing the boundaries of
Speaker 2: security by simulating real world attacks to uncover vulnerabilities that
Speaker 2: might otherwise go unnoticed.
Speaker 1: Okay, so it's not just about finding those obvious holes.
Speaker 1: It's about anticipating the unexpected, exact, the attacks that organizations
Speaker 1: haven't even considered yet.
Speaker 2: That's it. Chris truntz Are, one of the experts featured
Speaker 2: in the book, puts it perfectly. Red teaming is about
Speaker 2: finding those unknown unknowns rights, not just scanning for the
Speaker 2: known vulnerabilities. And that's what makes it such a valuable
Speaker 2: tool for organizations looking to stay ahead of the curve.
Speaker 1: That makes a lot of sense. So how does someone
Speaker 1: even begin to think like a red teamer? Yeah? Is
Speaker 1: it a skill you can learn or some people just
Speaker 1: naturally wire that way?
Speaker 2: Well, a lot of the experts, like Rob Fuller and
Speaker 2: David Kennedy empatasize the importance of understanding the blue team perspective.
Speaker 1: Interesting.
Speaker 2: Red teamors need to be able to anticipate how defenders
Speaker 2: think in order to out maneuver them. It's almost like
Speaker 2: a game of chess.
Speaker 1: I get it. Yeah, you have to know your opponent's
Speaker 1: moves to stay one step ahead exactly. Yeah.
Speaker 2: And Mike Sharon talks about cultivating that hacker mindset a
Speaker 2: blend of skepticism tenacity and a relentless drive to find
Speaker 2: another way in even when the obvious paths are blocked.
Speaker 1: So it's not just about technical skills, right, it's a
Speaker 1: way of thinking, a relentless curiosity to find the weak spots.
Speaker 2: It is you're catching on quickly. Justin Ell sums it
Speaker 2: up well. Good red teamers are creative problem solvers, able
Speaker 2: to adapt when a tax fail and find new paths.
Speaker 1: It sounds like you need a pretty unique blend of
Speaker 1: technical chops. Yeah, and those softer skills like communication, teamwork.
Speaker 2: You're absolutely right. Several of the experts stress the importance
Speaker 2: of communication, teamwork and ethics. You need the technical skills
Speaker 2: to execute the attacks, but you also need to work
Speaker 2: effectively as a team, communicate your findings clearly, and of course,
Speaker 2: operate ethically.
Speaker 1: Makes sense. Speaking of technical skills, what specific areas do
Speaker 1: red teamers need to be proficient in? Oh, definitely, I
Speaker 1: imagine it's a pretty extensive list.
Speaker 2: Rob Fuller gives a pretty comprehensive overview in the book,
Speaker 2: and it really is quite a range. Routing, switching, active directory, wireless,
Speaker 2: physical security, wow IoT, web applications, cloud environments. That's a lot,
Speaker 2: it seems like every aspect of it is fair game.
Speaker 1: Wow, that's a lot to master. Yeah, it really highlights
Speaker 1: the sheer complexity of cybersecurity these days, doesn't it.
Speaker 2: It absolutely does, And bo Bullock makes a good point
Speaker 2: that many Red teamers actually specialize in certain areas, which
Speaker 2: makes them even more valuable assets to a team. So
Speaker 2: you might have someone who's an expert in exploiting active
Speaker 2: directory while another focuses on social engineering or physical security breaches.
Speaker 1: Okay, so let's say someone is intrigued by all this
Speaker 1: and wants to get into red teaming. What advice did
Speaker 1: these experts have for aspiring Red teamers.
Speaker 2: Well, there's a pretty consistent theme that comes up again
Speaker 2: and again. Hands on experience is crucial. So things like
Speaker 2: building your own lab, participating in bug bounty programs, and
Speaker 2: getting involved in Capture the Flag CTF competitions are all
Speaker 2: highly recommended.
Speaker 1: So it's like anything else, you can't just read about
Speaker 1: it again, you have to roll up your sleeves and
Speaker 1: actually do it. You got it.
Speaker 2: And several of the experts emphasize the power of networking,
Speaker 2: attending conferences, going to meetups, connecting with people in the field,
Speaker 2: building relationships and learning from others is so valuable, especially
Speaker 2: in a fast paced field like cybersecurity.
Speaker 1: That makes total sense.
Speaker 2: Learning from people who are actually out there doing the work.
Speaker 1: Yeah.
Speaker 2: I can definitely see the value in that.
Speaker 1: Absolutely Yeah. And Jared Fulkens makes a really interesting point
Speaker 1: about the value of real world experience, even if it's
Speaker 1: not directly related to red teaming. He talks about how
Speaker 1: working on blue teams, doing system administration or even programming,
Speaker 1: can give you a deeper understanding of how systems work
Speaker 1: and how they can be exploited.
Speaker 2: So it's not just about being a hacker, it's about
Speaker 2: having a well rounded foundation in it, exactly.
Speaker 1: Yeah. Now, let's shift gears a bit and talk about
Speaker 1: red team reporting.
Speaker 2: Right. Here's where it gets interesting, because it's not just
Speaker 2: about finding the vulnerabilities, it's about communicating them effectively.
Speaker 1: You're absolutely right.
Speaker 2: Yeah.
Speaker 1: The book really stresses that reports need to be actionable
Speaker 1: and provide context for the client. It's not about showing
Speaker 1: off your skills. It's about helping the organization improve its
Speaker 1: security posture. So it's about painting a clear picture it
Speaker 1: is of the vulnerabilities and what the organization can do
Speaker 1: to address them. I imagine that requires a certain level
Speaker 1: of storytelling, right it does. You can't just throw a
Speaker 1: bunch of technical jargon at them and expect them to understand.
Speaker 2: Patrick Sassel actually compares Red Team reporting to storytelling interesting.
Speaker 2: He says, you need to use things like attack maps
Speaker 2: and clear descriptions to explain the attack path, almost like
Speaker 2: you're taking the client on a journey through the breach.
Speaker 1: I love that analogy. It makes the findings come alive
Speaker 1: and helps the client understand the real world impact.
Speaker 2: Of those vulnerabilities.
Speaker 1: And Jared Hate emphasizes the importance of collaborating with the
Speaker 1: Blue Team. It's about working together to get a complete
Speaker 1: picture of the organization's security posture and develop a shared
Speaker 1: understanding of the risks.
Speaker 2: That makes a lot of sense.
Speaker 1: It's not about Red Team versus Blue Team. It's about
Speaker 1: both teams working together achieve a common goal, which is
Speaker 1: improving the organization's security.
Speaker 2: Right now, speaking of teamwork and collaborations, you're ready for
Speaker 2: some stories from the field.
Speaker 1: Oh absolutely, I'm always up for a good story laid
Speaker 1: on me well. Christopher Campbell shared a particularly memorable one.
Speaker 1: He was on an engagement and accidentally triggered an alert
Speaker 1: during a meeting with the entire IA section.
Speaker 2: Oh no, what happened?
Speaker 1: He was using compromised credentials and the target machine was
Speaker 1: actually being used to project slides for the meeting. Oh wow,
Speaker 1: So the IA team immediately saw his IP address. Oh
Speaker 1: and the account he was using.
Speaker 2: Oh that's got to be awkward. Yeah, talk about being
Speaker 2: caught red handed.
Speaker 1: How do he react? Well, in a moment of quick thinking,
Speaker 1: he decided to maintain character and pretend he was supposed
Speaker 1: to be there.
Speaker 2: Oh my gosh. He even told the IA team to
Speaker 2: go get their boss.
Speaker 1: Wow. Talk about thinking on your feet. No right, did
Speaker 1: they buy it?
Speaker 2: Not first? Okay, but he managed to stall them long
Speaker 2: enough to escape the conference room.
Speaker 1: That's a classic Red Team remove right. Always be prepared
Speaker 1: for the unexpected, always. But these Bursted stories, while entertaining,
Speaker 1: also raise some important questions about the ethical considerations that
Speaker 1: Red teamers face. What happens when they find something truly disturbing.
Speaker 2: It's a tricky situation, for sure.
Speaker 1: Yeah.
Speaker 2: A few of the experts mentioned finding things like evidence
Speaker 2: of illegal activities. Oh wow, during their engagements.
Speaker 1: That must be a tough position to be in, it is.
Speaker 1: What's the protocol in those situations.
Speaker 2: Well, it really depends on the rules of engagement okay
Speaker 2: for that specific project, Yeah, and the client's policies. But
Speaker 2: it highlights the importance of having those conversations up front
Speaker 2: and making sure everyone is on the same page about
Speaker 2: how to handle sensitive discoveries.
Speaker 1: It really brings to light the human side of red peeming,
Speaker 1: doesn't it.
Speaker 2: It does.
Speaker 1: It's not just about tech nical skills. It's about navigating
Speaker 1: complex situations and making judgment calls.
Speaker 2: Chris Nickerson really drives this point home in the book.
Speaker 2: He says Red teamers are not just robots. They are
Speaker 2: passionate about security and making a difference.
Speaker 1: And that passion is often what makes them so effective. Absolutely,
Speaker 1: they're not just going through the motions. They genuinely care
Speaker 1: about improving security.
Speaker 2: Exactly, and that shared passion often leads to a strong
Speaker 2: sense of Camarrie mutual respect between the Red and Blue teams.
Speaker 2: Even though they're essentially on opposite sides, they understand that
Speaker 2: they're both working towards the same goal and the more
Speaker 2: secure world.
Speaker 1: Okay, so we've talked about the skills, the mindset, the ethics,
Speaker 1: even some of the funny mishaps that can happen in
Speaker 1: the field, But what are some of the qualities that
Speaker 1: make a truly exceptional red teamer stand out?
Speaker 2: Well? Jared Hate talks about how the best Red teamers
Speaker 2: are never satisfied even when they achieve their objective. They're
Speaker 2: constantly analyzing, looking for ways to improve, thinking about how
Speaker 2: the blue team could have detected them. Okay, they're essentially
Speaker 2: red teaming themselves.
Speaker 1: Wow, that's some next level dedication. Always striving for improvement.
Speaker 2: Exactly, and over time they develop an incredible intuition. Patrick
Speaker 2: Fasol describes it as being able to look at a
Speaker 2: target and almost instantly get a sense of its security
Speaker 2: and maturity.
Speaker 1: That's amazing, Like they've developed a sixth sense for spotting vulnerabilities.
Speaker 2: It is.
Speaker 1: But they're not just relying on gut feeling right now. No,
Speaker 1: they're still doing their due diligence when it comes to
Speaker 1: planning and research.
Speaker 2: They still spend a lot of time gathering information and
Speaker 2: planning their attacks. That reconnaissance phase is crucial because the
Speaker 2: more you know about the target, the more efficient and
Speaker 2: effective your attack will be.
Speaker 1: Makes sense. Knowledge is power, as they say.
Speaker 2: And here's another interesting observ from the book, The Best
Speaker 2: Red teamers are often indistinguishable from the best Blue teamers.
Speaker 1: Wait, really, but aren't they on opposite sides in a sense? Yes,
Speaker 1: how does that work?
Speaker 2: Well? The top practitioners in both fields have such a
Speaker 2: deep understanding of security that they can easily switch perspectives.
Speaker 2: They understand the attack vectors, the defense mechanisms, and the
Speaker 2: thought processes on both sides.
Speaker 1: That's incredible. So they could potentially infiltrate a system pretty
Speaker 1: much and defend it with equal skill.
Speaker 2: They know the game inside and out. Wow, and that
Speaker 2: really reinforces the importance of collaboration. Red and Blue teams
Speaker 2: need to work together, share their knowledge, and learn from
Speaker 2: each other to create a truly robust security posture.
Speaker 1: Iron sharpens iron.
Speaker 2: Exactly, and sometimes that collaboration leads to some pretty hilarious moment.
Speaker 1: I'm all airs, tell me another story.
Speaker 2: Uns are shared one about a time he was on
Speaker 2: an engagement and accidentally compromised a system. It was broadcasting
Speaker 2: a weather report on TVs throughout the entire organization.
Speaker 1: Oh no, everyone must have seen him hacking.
Speaker 2: Am Amazingly, no one noticed for almost twenty four hours.
Speaker 1: Wow.
Speaker 2: The point of contact only realized something was wrong when
Speaker 2: the weather image disappeared from the TVs.
Speaker 1: That's hilarious. It just goes to show that even the
Speaker 1: most sophisticated security systems can have unexpected blind spots. And
Speaker 1: it also highlights the human element of cybersecurity. People can
Speaker 1: be the weakest link, but they can also be the
Speaker 1: strongest asset. That's true. So what's the takeaway here for organizations?
Speaker 1: How can they take all these insights from these red
Speaker 1: teaming experts and apply them to their own security practices.
Speaker 2: Well, I think the biggest takeaway is.
Speaker 1: That organizations need to invest in both technology and people.
Speaker 1: Having strong security controls is important, but they're useless without
Speaker 1: a skilled team to manage them and a culture that
Speaker 1: embraces a security first mindset.
Speaker 2: So it's about having the right tools and the right
Speaker 2: people and creating an environment where security is everyone's responsibility.
Speaker 1: Right. Organizations need to encourage that red team mindset, that
Speaker 1: culture of curiosity, skepticism, yeah, and continuous improvement. Don't just
Speaker 1: accept the status quo. Constantly question, test and challenge your assumption.
Speaker 2: I love that. Always be learning, always be adapting exactly.
Speaker 1: And finally foster that collaboration between red and blue teams.
Speaker 1: Break down the silos, encourage information sharing and work together
Speaker 1: to create a more secure environment.
Speaker 2: This deep dove has been so insightful. H I feel
Speaker 2: like I have a whole new understanding of the world
Speaker 2: of red teaming and.
Speaker 1: How valuable it is for organizations. It is, But what
Speaker 1: about the future of red teaming? Where do things go
Speaker 1: from here? The threat landscape is constantly evolving, it is,
Speaker 1: so I imagine red teaming has to evolve as well.
Speaker 2: Right, that's a great question.
Speaker 1: Yeah.
Speaker 2: Several experts in the book shared their thoughts the future
Speaker 2: of red teaming, and one theme that came up repeatedly
Speaker 2: was the rise of automation and AI.
Speaker 1: Oh that's interesting. How do you think those technologies are
Speaker 1: going to impact red teaming?
Speaker 2: Well, on the one hand, okay, they have the potential
Speaker 2: to make red teamors jobs a lot easier. Automated tools
Speaker 2: can help with tasks like reconnaissance and vulnerability scanning, freeing
Speaker 2: up red teamers to focus on more strategic, creative aspects
Speaker 2: of the attack.
Speaker 1: So it's like having a digital assistant to take care
Speaker 1: of some of the grunt work exactly.
Speaker 2: On the flip side, the increasing adoption of AI and
Speaker 2: automation by security teams also presents new challenges for Red teamers.
Speaker 1: How So, you'd think having more automation would make things
Speaker 1: easier for attackers too.
Speaker 2: Right, Not necessarily. As defenders start using more sophisticated AI
Speaker 2: powered security tools, attackers will need to develop new techniques
Speaker 2: to bypass them. It's an ongoing arms.
Speaker 1: Race, so Red teamers will need to constantly adapt, yes,
Speaker 1: learn new skills, and develop new tactics to stay ahead
Speaker 1: of the game.
Speaker 2: Absolutely, and that's where the human element becomes even more important.
Speaker 1: Why is that? Wouldn't you think AI would eventually make
Speaker 1: human Red teamers obsolete?
Speaker 2: Not quite. There are certain things that AI and automation
Speaker 2: simply can't replicate, things like creativity, intuition, critical thinking, and
Speaker 2: the ability to adapt to unforeseen circumstances.
Speaker 1: It's that uniquely human ability to think outside the box, yes,
Speaker 1: and come up with creative solutions that AI can't quite
Speaker 1: grasp yet exactly.
Speaker 2: So, I think the future of Red teaming will involve
Speaker 2: a blend of human expertise and technological advancements. It's about
Speaker 2: finding the right balance between automation and human ingenuity.
Speaker 1: That makes sense. It's about leveraging technology to enhance human
Speaker 1: capabilities not replace them.
Speaker 2: Entirely, and as the threat landscape becomes even more complex
Speaker 2: and sophisticated, red teamers will play an increasingly important role
Speaker 2: in helping organizations stay ahead of the curve.
Speaker 1: I completely agree they're the unsung heroes of cybersecurity. Yeah,
Speaker 1: constantly pushing the boundaries, challenging the status quo, and helping
Speaker 1: organizations build more resilient defenses.
Speaker 2: They are, indeed, and this deep dive, while thorough, has
Speaker 2: really just scratched the surface of the world of red teaming.
Speaker 2: There's so much more to explore, so many fascinating stories
Speaker 2: to tell, and so many brilliant minds working in this field.
Speaker 1: I'm already looking forward to our next deep dive in
Speaker 1: the world of cybersecurity.
Speaker 2: They do.
Speaker 1: But before we wrap up completely, let's leave our listeners
Speaker 1: with a final thought, something to ponder as they continue
Speaker 1: their own explorations in the world of cybersecurity. What if
Speaker 1: we took everything we've learned about red teaming and applied
Speaker 1: it to our own lives, kind of like a personal
Speaker 1: security audit.
Speaker 2: I love that idea red team in your life. It's
Speaker 2: a really interesting concept. Think about it. What are your
Speaker 2: personal vulnerabilities? What are the threats you face on a
Speaker 2: daily basis, and what steps can you take to strengthen
Speaker 2: your own security posture.
Speaker 1: Okay, let's unpack this personal vulnerabilities. Well, I'll admit yeah,
Speaker 1: I'm probably guilty of oversharing on social media, sometimes not
Speaker 1: giving away any state secrets or anything, probably more than
Speaker 1: I should.
Speaker 2: That's a really common one, and it's a perfect example
Speaker 2: of how those red teaming principles can apply to everyday life. Right,
Speaker 2: put on your attacker hat for a second. Okay, what
Speaker 2: kind of information could someone use against you?
Speaker 1: My social media posts could give away my location, routine,
Speaker 1: my interests, all valuable intel for someone looking.
Speaker 2: To take advantage exactly, So how could you mitigate that risk?
Speaker 1: Well, for starters, I could be more mindful about what
Speaker 1: I post, I could tweak my privacy settings, be careful
Speaker 1: about tagging my location, and definitely avoid posting sensitive information.
Speaker 2: Those are all great steps, and it's not just about
Speaker 2: online security either. Think about your physical security as well.
Speaker 1: Good point, I should probably be more diligent about locking
Speaker 1: my doors and windows, especially when I'm not home.
Speaker 2: And what about your devices? Do you have strong passwords?
Speaker 2: Do you use two factor authentication? These are all basic
Speaker 2: security hygiene practices that can make a big difference.
Speaker 1: Okay, you're making me really, I have some work to do.
Speaker 1: I definitely need to step up my personal security game.
Speaker 2: We all do. It's an ongoing process, just like red
Speaker 2: teaming for organizations. It's about being proactive, anticipate threats and
Speaker 2: taking steps to mitigate those risks.
Speaker 1: So the key takeaway here, yeah, is to apply those
Speaker 1: same principles of red teaming to our own lives.
Speaker 2: Exactly.
Speaker 1: Think like an attacker, identify your vulnerabilities and strengthen your defenses.
Speaker 2: Precisely, take control of your own security and protect yourself
Speaker 2: from potential harm.
Speaker 1: I love that red team in your life. Yeah, it's
Speaker 1: a brilliant concept, it is, and something we can all
Speaker 1: benefit from.
Speaker 2: Absolutely. It's all about empowering yourself with knowledge, right and
Speaker 2: taking those proactive steps to stay safe.
Speaker 1: This deep dive has been incredible. It has I feel
Speaker 1: like I've gained a whole new perspective on cybersecurity. Yeah,
Speaker 1: both professionally and personally.
Speaker 2: Me too. Yeah, it's been fascinating exploring the world of
Speaker 2: red teaming, yeah, and all its intricacies.
Speaker 1: So to our listeners, we encourage you to keep exploring,
Speaker 1: keep learning, and keep red teaming your way to a
Speaker 1: more secure future.
Speaker 2: And remember security is not a destination, it's a journey.
Speaker 2: Stay stay informed, and stay ahead of the game.
Speaker 1: Thanks for joining us for this deep dive into the
Speaker 1: world of red teaming.
Speaker 2: It's been fun.
Speaker 1: We'll see you next time. See you for another fascinating
Speaker 1: exploration of the world of cybersecurity.