The Pentester BluePrint: Starting a Career as an Ethical Hacker - podcast episode cover

The Pentester BluePrint: Starting a Career as an Ethical Hacker

Mar 22, 202523 min
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Episode description

"The Pentester Blueprint" is a guide to becoming an ethical hacker (pentester). The book covers the necessary technical skills, including operating systems, networking, and programming, as well as the "hacker mindset." It details various pentesting methodologies and exploits, emphasizing legal and ethical considerations. The authors also discuss educational resources, certification paths, and job searching strategies for aspiring pentesters, drawing from interviews with professionals in the field.

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Transcript

Speaker 1

All right, let's dive in. Today we're exploring the world of ethical hacking better known as penetration testing.

Speaker 2

Really fascinating stuff and you know, I'm.

Speaker 1

Really excited to be breaking down this whole career path, especially with this book, The pen Tester Blueprint you sent over.

Speaker 2

Yeah, it's like the ultimate guide for anyone dreaming of becoming a pen tester.

Speaker 1

Okay, so first things first, what exactly is a penetration tester? I mean, we hear ethical hacker, but what's the day to day look like.

Speaker 2

Well, imagine this. You're hired by a company to basically try and break into their systems.

Speaker 1

Whoa So just like a real attacker would.

Speaker 2

Exactly, but with one big difference. You have their permission and it's all above board.

Speaker 1

Legally, So no sneaking around in the dark, not at all.

Speaker 2

It's all about finding those vulnerabilities before the bad guys do.

Speaker 1

Right, so they can beef up their security exactly.

Speaker 2

And the book really stresses the importance of having everything in writing, a clear agreement outlining the scope, the targets, all the rules of engagement.

Speaker 1

Okay, that makes sense. So you're like a digital detective uncovering weaknesses that.

Speaker 2

Can be patched up A great way to put it.

Speaker 1

Now. The book mentions methodologies like PT and OOS are those like the Detective's Handbook exactly.

Speaker 2

Think of them as structured approaches to pen testing, ensuring thoroughness and consistency.

Speaker 1

So there's a method to the madness, not just random hacking.

Speaker 2

Right. Take the O was P Testing Guide for example. It breaks down the testing process for web applications into super specific areas like authentication, authorization, data validation. It's a real roadmap.

Speaker 1

Wow. So it's not just like poking around hoping to find a hole. There's an actual science to it.

Speaker 2

There is, and there are different phases too, like what Well, first, there's information gathering, learning everything you can about the target, kind of like reconnaissance on a digital battlefield.

Speaker 1

Scoping out the terrain before you make your move. Makes sense. What comes after reconnaissance?

Speaker 2

Then comes vulnerability analysis, using various tools and techniques to uncover weaknesses and systems and applications.

Speaker 1

Okay, and then the exciting.

Speaker 2

Part, the exciting part, yes, exploitation. You actually try to break in, but ethically remember and always within that agreed upon.

Speaker 1

Scope right to see what an attacker could do, not to cause damage exactly.

Speaker 2

Then there's post exploitation figuring out just how much damage could be done, stealing data, disrupting operations.

Speaker 1

That kind of thing sounds intense.

Speaker 2

And finally reporting, Yeah, you provide the company with a detailed roadmap for fixing those vulnerabilities.

Speaker 1

So it's a whole process from start to finish, it is. Yeah.

Speaker 2

And speaking of different approaches, you know the book talks about black box, white box, and gray box testing.

Speaker 1

Yeah, I was curious about those. Can you break them down for us?

Speaker 2

Okay? Imagine being dropped into a totally unknown city. Your mission find a specific building, no map, no guide, just your skills and intuition. That's black box testing.

Speaker 1

Wow, that sounds tough. Okay, Then what's white box?

Speaker 2

Whitebox is the complete opposite. You're giving blueprints to the city, street names, building layouts, you know exactly where to go.

Speaker 1

Ah, so you have all the information you need exactly And gray box I'm guessing it's somewhere in between.

Speaker 2

You got it. Gray box is like having a partial map, maybe some street names, but not all the details.

Speaker 1

Interesting, So different levels of knowledge about the target makes sense. Now let's talk skills. What do you need to know to become a pentester. The book mentions operating systems, networking, cybersecurity fundamentals.

Speaker 2

Those are the building blocks, the foundation, like trying to break into a house without knowing how doors and windows work.

Speaker 1

So operating systems you have to know Windows, Linux, all those inner workings.

Speaker 2

Absolutely, you need to understand how they function to even think about exploiting them.

Speaker 1

Makes sense.

Speaker 2

And then networking that's like understanding the roads and highways that connect those houses, how data flows, how networks are.

Speaker 1

Structured right to see where the weak points might be exactly.

Speaker 2

And then cybersecurity fundamentals those are like the overall rules of.

Speaker 1

The game, the ground rules.

Speaker 2

I get it right, understanding concepts like the CIA triad, confidentiality, integrity, availability. It's about protecting data from all angles.

Speaker 1

Protecting it from unauthorized access, making sure it's not corrupted, and making sure it's accessible to the right people.

Speaker 2

Got it exactly. It's a holistic approach.

Speaker 1

Okay, so it's more than just hacking skills. You need a deep understanding of how everything works together.

Speaker 2

Right, And then they're social engineering. That's a fascinating area.

Speaker 1

Yeah, the book touched on that. Tell me more.

Speaker 2

It's all about the human element, exploiting human behavior to get access to information.

Speaker 1

So basically hacking the human operating system exactly.

Speaker 2

Things like phishing attacks where people are tricked into clicking malicious links or revealing sensitive information.

Speaker 1

Wow, so you're playing on people's trust and habits.

Speaker 2

In a way. Yes, it's about understanding how people think, how they react, and how to exploit those patterns.

Speaker 1

Okay, this is getting really interesting. It's like a blend of technical skills, psychology, even detective work.

Speaker 2

That's a great way to put it. And it's constantly evolving, just like technology itself.

Speaker 1

Right, always changing new challenges. Now, the book talks about building a pen testing lab. What exactly is that?

Speaker 2

It's like having your own personal hacking playground?

Speaker 1

Whoa seriously?

Speaker 2

Yeah, a safe space where you can experiment and practice hone your skills without any real world consequences.

Speaker 1

Okay, a hacking playground. I like the sound of that. But how do you even set one up?

Speaker 2

It can be simple or complex depending on your goals. The book outlines different setups using virtualization software like Oracle virtual.

Speaker 1

Box, virtual box. Okay, what does that do?

Speaker 2

It lets you create virtual machines, essentially simulated computers. On your existing computer.

Speaker 1

So I could have a virtual Windows machine, a virtual Linux machine.

Speaker 2

Exactly, all running safely on your own system, ready for you to practice on. You can even download pre built intentionally vulnerable virtual machines.

Speaker 1

Whoa intentionally vulnerable? Why would you do that?

Speaker 2

So you can practice exploiting those known vulnerabilities in a safe environment.

Speaker 1

Ah, like a training ground with preset targets exactly.

Speaker 2

You can find those on sites like bal hub.

Speaker 1

Okay, so you've got your virtual lab, your virtual targets. That's pretty high tech. What kind of tools do pen testers actually use?

Speaker 2

There's a whole arsenal out there. The book dives into a bunch of them. A good place to start is Kalie Linux.

Speaker 1

Kalie Linux, I've heard that name before. Sounds intense.

Speaker 2

It's a penetration testing focused operating system. It comes with a huge collection of tools already built in.

Speaker 1

Well, that's convenient. So what kind of tools are we talking about?

Speaker 2

Well, there's NMP for network scanning, wire Shark for analyzing network traffic, metasploit for developing and executing exploits.

Speaker 1

Okay, those names are starting to ring a bell.

Speaker 2

End map is like a radar for the digital world. It lets you map out a network, see what's out there. Wire Shark, on the other hand, is more like a microscope, letting you dissect network traffic and see how systems are communicating, so.

Speaker 1

You can see what's being said, so to speak, exactly.

Speaker 2

And then there's metasploit, which provides a structured approach to penetration testing.

Speaker 1

Okay, so each tool has its own specialty.

Speaker 2

Exactly, and as you progress, you might even start building your own custom tools and scripts.

Speaker 1

Wow, that sounds really advanced. But before we get there, let's talk about actually getting started in this field. It's not like you can just walk into a company and say, hey, I'm a hacker. Hire me.

Speaker 2

Well, the demand for skilled pen testers is definitely growing, but it's still a competitive.

Speaker 1

Field, right, So what do you need to do to stand out?

Speaker 2

The book really emphasizes certifications, practical experience, and networking.

Speaker 1

Okay, so let's start with certifications. What are some key ones to consider?

Speaker 2

Well, there's the Certified Ethical Hacker CEH, COMPTIAPEN test plus, Compact Offensive Security Certified Professional or OSCP.

Speaker 1

Okay. Lots of acronyms are these like digital badges saying hey, I know my stuff.

Speaker 2

They're more than just badges. They show a real commitment to professional development and a recognition of your skills by the industry.

Speaker 1

So they hold some weight.

Speaker 2

They do. CP for example, is known for his hands on exam. You actually have to penetrate a simulated network to pass.

Speaker 1

Wow, a real test of your abilities. So certifications are important, but what about practical experience? How do you get that before applying for jobs?

Speaker 2

That's where Capture the Flag competitions come in or CTFs.

Speaker 1

Capture the Flag sounds fun they are.

Speaker 2

Think of them as digital treasure hunts for cybersecurity enthusiasts. You're presented with challenges and have to find hidden flags to solve them.

Speaker 1

Ah, I see, so like a real world simulation, but in a controlled environment exactly.

Speaker 2

You get to apply your skills, learn new techniques and they look great on a resume.

Speaker 1

Right shows you're proactive, always learning.

Speaker 2

Exactly, and they're fun. You can participate online from anywhere.

Speaker 1

Cool. So CTFs are a great way to build up experience. Now what about those bug bounty programs? The book mentions what are those all about?

Speaker 2

Bug bounty programs are another great way to gain experience and maybe even earn some money along the way.

Speaker 1

Wait, getting paid to hack sort of.

Speaker 2

Company invite security researchers to find and report vulnerabilities in their systems.

Speaker 1

So you're basically a paid consultant helping them find weak spots before the bad guys do.

Speaker 2

Exactly, and the rewards can be pretty significant. Some programs offer thousands of dollars for finding critical vulnerabilities.

Speaker 1

Wow, so you're getting experience and getting paid for it.

Speaker 2

It's a win win, and it's a great way to build your reputation in the security community. Finding a big vulnerability can get you noticed by top companies.

Speaker 1

Okay, CTFs for skills, bug bounties for real world testing, and maybe some cash. Sounds like a good path. But what about for total beginners? Where do you even start?

Speaker 2

The best advice is to start small. Don't try to tackle the most complex challenges right away, right work your way up exactly. There are plenty of beginner friendly CTF platforms and bug bounty programs out there. Just jump in and try things out.

Speaker 1

Don't be intimidated, not at all.

Speaker 2

Everyone starts somewhere. Just be curious, keep learning, and don't give up. That's what the he hacker mindset is all about.

Speaker 1

Okay, the hacker mindset. We touched on that earlier. What does it really mean to think like a hacker?

Speaker 2

It's about curiosity, creativity and always wanting to learn more, looking at systems and processes and thinking how could this be exploited?

Speaker 1

So it's not about being malicious, it's about understanding how someone could be malicious exactly.

Speaker 2

Ethical hackers use that mindset to find vulnerabilities so they can be fixed, not exploited. Think like the bad guys so you can.

Speaker 1

Stay ahead of them, right like those chess grant masters who can think dozens of moves ahead.

Speaker 2

That's a great analogy. And just like chess, it takes practice to develop that kind of thinking. You need to be always learning, experimenting, challenging yourself to think differently.

Speaker 1

So how do you actually develop that mindset? Any tips or tricks?

Speaker 2

One thing you can try is to look at everyday objects or processes and break them down. Ask yourself how they work, how they could be manipulated, where the weaknesses might be.

Speaker 1

So like, instead of just using my coffeemaker, I should be thinking of about how it could be hacked.

Speaker 2

Exactly. It's about looking at the world with a different perspective, always asking what if.

Speaker 1

That's a really interesting way to think about it. It's almost like a philosophy, a way of approaching problems in general, you could.

Speaker 2

Say that and is a valuable skill in lots of areas, not just cybersecurity.

Speaker 1

Okay, so we've got the skills, the experience, the mindset. What else is important for aspiring pen testers to keep inhind.

Speaker 2

Well, the world of cybersecurity is constantly changing. There are always new challenges and trends.

Speaker 1

Emerging, so you always have to be learning and adapting exactly.

Speaker 2

One of the biggest challenges right now is just the sheer complexity of systems and networks. Everything is connected and it's constantly growing, like.

Speaker 1

Trying to find a needle in a haystack that keeps getting bigger, right, And.

Speaker 2

There are so many different types of systems and technologies now, cloud computing, mobile devices, the Internet of Things. It's a lot to keep up with.

Speaker 1

So pen testers need to be really versatile and adaptable.

Speaker 2

Absolutely, you can't just specialize in one area anymore. You need to be knowledgeable across a wide range of platforms and technologies.

Speaker 1

Like a doctor who needs to be able to treat all kinds of different conditions.

Speaker 2

Exactly, and you need to stay up to date on the latest research, just like a doctor would, always learning about new vulnerabilities and.

Speaker 1

Attack techniques, right, always evolving. So with all these challenges, are there still opportunities in this field?

Speaker 2

Oh? Absolutely lots of them. One area that's really booming right now is cloud security. More and more companies are moving their data and applications to the cloud, so they need people who understand how to secure those environments.

Speaker 1

Makes sense. So it's not just about physical servers and networks.

Speaker 2

Anymore, right, It's a whole new frontier with its own unique set of challenges and opportunities.

Speaker 1

So the field is growing and changing all the time.

Speaker 2

It is, and as long as there's technology, there will be a need for skilled pen testers.

Speaker 1

That's really reassuring to hear. It sounds like a challenging but really exciting field to be in.

Speaker 2

It is, and it's really rewarding knowing your help to make the digital world a safer place.

Speaker 1

Well, you've definitely given me a lot to think about. I'm sure our listeners are feeling inspired too. Any final thoughts or advice for those who want to explore this path.

Speaker 2

The most important thing is to stay curious, never stop learning, experimenting, pushing the boundaries of your knowledge.

Speaker 1

Embrace that hacker mindset exactly, and remember it's a journey, not a destination.

Speaker 2

There's always something new to learn, new challenges to tackle, and never forget the ethical side of things. Use your skills for good.

Speaker 1

So stay curious, stay ethical, and never stop exploring. Great advice.

Speaker 2

Well, we've covered a lot of ground today. The world of penetration testing is clearly complex and constantly evolving. It definitely is, but also incredibly fascinating. Thanks so much for taking this deep dive with us today.

Speaker 1

It's been my pleasure. Welcome back.

Speaker 2

All right, So, last time we got a taste of the skills and tools pen testers use.

Speaker 1

Yeah, just a taste. But today let's get into the real world inside of things exactly.

Speaker 2

And I know we have to talk about those Capture the Flag competitions.

Speaker 1

Oh yeah, the CTFs. Those are like digital obstacle courses for cybersecurity folks.

Speaker 2

Okay, obstacle courses. I like that. So how do they work?

Speaker 1

You basically face a bunch of challenges and you have to use your knowledge and skills to find hidden.

Speaker 2

Flags flags, Like what kind of flags?

Speaker 1

They could be anything a piece of text, a code, anything hidden within the system. Interesting. So it's like a Stavenger Hunt, but for hackers exactly.

Speaker 2

And you can do them online from anywhere.

Speaker 1

Cool, so anyone can participate.

Speaker 2

Yep. There are CTFs for all skill levels, beginners to pros. Some you do solo, others are team events.

Speaker 1

So you can really test yourself and see how you stack up.

Speaker 2

Right, And they're not just for fun. CTFs look amazing on a resume. It shows potential employers that you're serious about cybersecurity.

Speaker 1

Oh, that makes sense. It shows you're actually applying what.

Speaker 2

You know exactly. Plus you're learning new techniques, getting familiar with real world scenarios.

Speaker 1

It's like a training simulation for actual hacking.

Speaker 2

That's a great way to put it. You're getting experience, but in a safe environment, right.

Speaker 1

No real world consequences if you make a mistake, exactly.

Speaker 2

So CTFs are awesome for building your skills. And then they're bug bounty programs.

Speaker 1

Yeah, we touched on those earlier. Remind me how those work again.

Speaker 2

So companies will actually pay you to find vulnerabilities in their systems.

Speaker 1

Wait, so I can get paid to hack.

Speaker 2

Well, it's ethical hacking. Remember you're working with their permission.

Speaker 1

Right, of course, So it's more like you're a consultant helping them improve their security exactly.

Speaker 2

And the rewards can be pretty sweet. Some programs offer thousands of dollars for critical vulnerabilities.

Speaker 1

Wow, that's pretty good. So you're learning, making a difference, and getting paid.

Speaker 2

Yeah, it's a great deal. Plus it's a great way to build your reputation.

Speaker 1

Makes sense. Companies are going to want to hire someone who's already proven they can find those vulnerabilities.

Speaker 2

And they might even hire you directly from a bug bounty program.

Speaker 1

Oh wow, so it's like a direct pipeline to a job.

Speaker 2

It can be.

Speaker 1

Yeah.

Speaker 2

So yeah, bug bounties are a fantastic opportunity.

Speaker 1

Okay, so we've got CTFs, bug bounties, lots of ways to get real world experience. Okay, but what about those of us who are just starting out. What's a good first step?

Speaker 2

Honestly, just pick something and try it. Don't be afraid to jump.

Speaker 1

In, even if you're a beginner.

Speaker 2

Especially if you're a beginner. There are CTF platforms and bug bounty programs specifically for people who are just starting out.

Speaker 1

Oh, good to know. So there are resources for every level.

Speaker 2

Yep. The key is to just be curious, keep learning, and don't get discouraged. That's really the foundation of the hacker mindset.

Speaker 1

Okay, the hacker mindset, we talked about it a bit before, but I feel like we could go deeper. What does it really mean to think like a hacker?

Speaker 2

It's all about curiosity, creativity and always questioning things, looking at a system and asking how could I break this?

Speaker 1

So it's not about wanting to break things, it's about understanding how they could.

Speaker 2

Be broken exactly. Ethical hackers use that knowledge to protect systems, not to exploit them.

Speaker 1

So you're always thinking a few steps ahead, anticipating the bad guy's moves exactly.

Speaker 2

And it takes practice to develop that kind of thinking. You have to challenge yourself to see things differently.

Speaker 1

Okay, so how do you actually do that? How do you train your brain to think that way?

Speaker 2

One way is to start looking at everyday things and try to break them down. Think about how they work, how they could be manipulated, where the weak points might be.

Speaker 1

So like looking at a door and thinking about all the ways you could pick the lock exactly.

Speaker 2

It's about seeing the world through a different lens.

Speaker 1

That's a cool way to think about it. It's almost like a superpower.

Speaker 2

It kind of is, yeah, and it's a useful skill to have in all sorts of situations, not just cybersecurity. Right.

Speaker 1

It's about problem solving, thinking outside the box. Okay, so we've covered a lot about becoming a pen tester, but what about the future of the field. What are some of the big challenges pen testers are facing these days?

Speaker 2

I think one of the biggest is just the sheer complexity of technology. Now everything is connected, Everything is evolving so quickly.

Speaker 1

It must be hard to keep up it is.

Speaker 2

You've got cloud computing, mobile devices, the Internet of things. It's a constantly moving target.

Speaker 1

So pen testers need to be super adaptable and always learning new things.

Speaker 2

Absolutely, you can't just be an expert in one area anymore. You need to have a broad understanding of how everything works together.

Speaker 1

Right. It's like being a doctor who has to treat all kinds of.

Speaker 2

Different patients exactly, and you always have to be learning new treatments and techniques. The field never stands still, so.

Speaker 1

Lots of challenges. But are there also new opportunities.

Speaker 2

Oh tons. One area that's really taking off is cloud security.

Speaker 1

Makes sense, that's where everything is moving.

Speaker 2

Right, and it's a whole new set of challenges. Pen testers need to understand how to secure those cloud environments.

Speaker 1

So it's like the wild West of cybersecurity kind of.

Speaker 2

There's so much to explore and so much room for growth.

Speaker 1

That's exciting. So it sounds like the future of pen testing is pretty bright, I think.

Speaker 2

So as long as there's technology, there will be a need for people who can find and fix vulnerability.

Speaker 1

That's good to hear. Well, this has been a really eye opening conversation. I'm sure our listeners are feeling inspired to learn more about this.

Speaker 2

World, I hope. So it's a fascinating field and there's always room for more talented people.

Speaker 1

All right, welcome back to our deep dive. We've covered a lot of ground on penetration testing, but there's one crucial element we need to discuss.

Speaker 2

Oh absolutely, we can't talk about ethical hacking without talking about ethics, right.

Speaker 1

So it's not enough to just be good at finding those vulnerabilities. You got to do it the right way exactly.

Speaker 2

Ethical hackers have a responsibility to use their knowledge for good to protect those systems, you know, not exploit them, right.

Speaker 1

Like you're being trusted with some pretty sensitive information.

Speaker 2

Sometimes it's a big responsibility, that's for sure. And that's why ethics is woven into every part of penetration testing, from the initial scope all the way to the reporting at the end.

Speaker 1

Okay, so can you give me some examples, like how do ethics actually play out during a pentest?

Speaker 2

Sure? And imagine you're testing a company's system and you find a vulnerability that gives you access to customer data.

Speaker 1

Oh, sensitive stuff.

Speaker 2

Right, as an ethical hacker, you have to report that vulnerability right away and not you.

Speaker 1

Know, go snooping around in people's data.

Speaker 2

Exactly. You only access what's absolutely necessary to show the impact of that vulnerability.

Speaker 1

Okay, So you're not trying to cause any harm, You're trying to prevent harm exactly.

Speaker 2

The goal is to help organizations make their security better, not to exploit weaknesses for personal gain.

Speaker 1

Right. So it's a fine line demonstrating the risk but not actually putting anything at risk.

Speaker 2

It is, and this ethical mindset goes beyond the technical stuff. It's about confidentiality, respecting agreements, always putting the client's best interests first.

Speaker 1

So ethical hacking is about character, not just skills.

Speaker 2

Absolutely, honesty, integrity, those are crucial qualities.

Speaker 1

Okay, I get that ethics are essential, but how do you ensure that all ethical hackers are actually following those principles.

Speaker 2

Well, that's where professional organizations and certifications come in.

Speaker 1

Right, those badges we talked about.

Speaker 2

Earlier Exactly, groups like the EC Council, they don't just validate your technical skills, they also emphasize ethical conduct.

Speaker 1

So you're not just proving you can do it, you're proving you'll do it the right way.

Speaker 2

Exactly. A lot of these certifications have a whole code of ethics that you're expected to follow.

Speaker 1

Ah, so it's like a hippocratic oath for ethical hackers.

Speaker 2

That's a great way to put it. And remember technology is always changing, so the ethical considerations they change too.

Speaker 1

Right, what might be okay today might not be okay tomorrow.

Speaker 2

Exactly. Ethical hackers have to stay informed, keep learning about new laws and best practices.

Speaker 1

So it's a continuous process of learning and adapting.

Speaker 2

Got it, exactly.

Speaker 1

Wow, We've covered a ton in this deep dive. Skills tools, real world experience, the hacker mindset, and now the ethics of it all. It's clearly a complex field but fascinating too.

Speaker 2

Really is challenging, but ultimately very rewarding.

Speaker 1

So for anyone listening who's thinking about dipping their toes into the ethical hacking waters, what advice would you give them?

Speaker 2

Never stop learning. Cybersecurity is constantly evolving, so stay curious, be part of the community, don't be afraid to ask questions.

Speaker 1

Embrace that hacker mindset of continuous learning and exploration.

Speaker 2

Yes, exactly, and remember it's not just about the technical stuff. Integrity and responsibility are just as important.

Speaker 1

Right, use your powers for good exactly.

Speaker 2

Have fun with it too. It's a challenging feel, but man, it's rewarding knowing you're making a difference in the world. That's a great feeling.

Speaker 1

Couldn't agree more. Well, this has been an incredible journey. A huge thank you for sharing your expertise and taking us on this deep dive into penetration testing.

Speaker 2

My pleasure. Always happy to spread the word about ethical hacking, and.

Speaker 1

So all our listeners out there, remember, stay curious, stay ethical, and never stop exploring the world of cybersecurity. This is a fascinating field and who knows. Maybe you will be the next generation of ethic hackers protecting the digital world. Thanks for joining us.

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