Speaker 1: Welcome back everyone to the deep dive. This time we're
Speaker 1: going deep into the world of penetration testing.
Speaker 2: Sounds intense, it is.
Speaker 1: But fascinating too. Our guide is the Hacker Playbook. This
Speaker 1: book is a gold mine of practical techniques, almost like
Speaker 1: a blueprint for ethical.
Speaker 2: Hacking, like a hacker's manual exactly.
Speaker 1: Imagine being hired to test the security of say a
Speaker 1: Fortune five hundred company.
Speaker 2: WHOA where do you even start with something like that?
Speaker 1: That's what we're going to uncover.
Speaker 2: Okay, I'm all ears.
Speaker 1: So the book uses this really interesting analogy of a
Speaker 1: football game to break down a penetration test.
Speaker 2: Okay, I like where this is gone.
Speaker 1: It has phases like the pregame, scanning the network, exploiting vulnerabilities,
Speaker 1: almost like planning a series of plays.
Speaker 2: So it's strategic very much.
Speaker 1: So it helps you see the big picture. Let's start
Speaker 1: with the pregame, which is all about setting up your
Speaker 1: tools and environment.
Speaker 2: Gotcha, getting your gear ready.
Speaker 1: And the book busted a myth for me. You don't
Speaker 1: need some crazy supercomputer to run these penetration testing tools.
Speaker 2: Really, that's good news for aspiring hackers, right.
Speaker 1: A decent computer that can handle a few virtual machines
Speaker 1: will do the trick. The book recommends Cali Linux.
Speaker 2: Ah Kali Linux the go to for pen testing.
Speaker 1: It's like your specialized toolbox for probing and testing.
Speaker 2: Systems, and it comes with a ton of pre installed
Speaker 2: tools right.
Speaker 1: Absolutely, And the best part is the book actually walks
Speaker 1: you through setting it up.
Speaker 2: That's helpful, especially for beginners. It's like having a coach guide.
Speaker 1: You precisely now. In this toolbox you'll find both open
Speaker 1: source and commercial tools. Industry standards like nessis, which is
Speaker 1: amazing for vulnerability scanning, and burp suite, which is super
Speaker 1: powerful for web application security testing.
Speaker 2: Those are big names. Yeah, but what if you're on
Speaker 2: a budget or just starting out.
Speaker 1: The book mentions OSPAP two it's a free alternative to
Speaker 1: burp Suite, great for getting your feet wet.
Speaker 2: That's good to know. Options are always good.
Speaker 1: Okay, So let's say we've got our toolbox ready, how
Speaker 1: do we even approach this massive fortune five hundred company network.
Speaker 1: It's got to be like a digital fortress, right, It's
Speaker 1: definitely a challenge. So where do we even begin?
Speaker 2: Well, you wouldn't storm a fortress without knowing the terrain, right,
Speaker 2: That's where scanning the network comes in.
Speaker 1: Okay, so we're scouting gathering intel exactly.
Speaker 2: The book breaks it down into two approaches, passive and
Speaker 2: active discovery.
Speaker 1: Passive inactive tell me more about those.
Speaker 2: Passive discovery is all about being stealthy. You're gathering information
Speaker 2: without directly interacting with the target network.
Speaker 1: So like observing from a distance looking for weak points.
Speaker 2: You got it. One technique they highlight is using discover scripts.
Speaker 1: What are those?
Speaker 2: They automate searches on sites like LinkedIn and use domain
Speaker 2: tools to uncover information.
Speaker 1: So you're like a digital detective piecing together clues precisely.
Speaker 2: Now, get this, Even old data breaches can be valuable.
Speaker 2: You can use those credential dumps to see if any
Speaker 2: employees might have reused their compromise passwords.
Speaker 1: Wow, that's clever using their own mistakes against them, right.
Speaker 2: It really shows how human behavior plays a big role
Speaker 2: in cybersecurity.
Speaker 1: People often reuse passwords for convenience, but it can have
Speaker 1: serious consequences.
Speaker 2: No doubt. And it's not just usernames and passwords. Think
Speaker 2: about all the other info companies might expose employee details,
Speaker 2: server names, software versions.
Speaker 1: All valuable intel for a penetration destric exactly.
Speaker 2: Every bit of information is a potential lead.
Speaker 1: Okay, So passive discovery is all about stealth and gathering
Speaker 1: intel without raising any alarms. What about active discovery? Is
Speaker 1: that when we start knocking on those digital doors.
Speaker 2: Yeah, you could say that active discovery involves probing the network,
Speaker 2: actively searching for live systems, open ports, running services, and vulnerabilities.
Speaker 1: So that's where those vulnerability scanners like NESSUS come in.
Speaker 2: Right, They automate a lot of that process.
Speaker 1: I'm pretty straightforward.
Speaker 2: It can be, but the book warns against relying solely
Speaker 2: on automated scans. They have their limitations.
Speaker 1: Why is that they were good at finding vulnerabilities?
Speaker 2: They are, but they might miss some. Oh some vulnerabilities
Speaker 2: need specific conditions to trigger. Others are hidden behind custom code.
Speaker 1: So manual probing is still important.
Speaker 2: It's crucial, especially when combined with a good understanding of
Speaker 2: networking and how things work.
Speaker 1: So it's about blending the power of those tools with
Speaker 1: human intuition and skill.
Speaker 2: That's the key. And understanding the tools themselves is important too.
Speaker 2: Like the book talks about customizing en map.
Speaker 1: Enmap that's a popular one.
Speaker 2: Right, Yeah, it's a network scanning tool. They show you
Speaker 2: how to tweak it for faster assessments.
Speaker 1: Cool any other interesting tools.
Speaker 2: There's peeping tom. This one's pretty cool. It takes screenshots
Speaker 2: of web services screen shots.
Speaker 1: Why is that helpful.
Speaker 2: When you're dealing with tons of websites. It gives you
Speaker 2: a quick visual overview. You can see what looks promising
Speaker 2: for further testing.
Speaker 1: Ah, I see Prioritizing targets exactly helps you focus your efforts. Now,
Speaker 1: speaking of websites, web app security is a huge part
Speaker 1: of penetration testing. What kind of tools and tactics are
Speaker 1: we talking about there?
Speaker 2: Web apps are often the most exposed part of a
Speaker 2: company's attack surface. It's where attackers love to strike. The
Speaker 2: book spends a lot of time on web app scanning,
Speaker 2: especially with burp suite pro so.
Speaker 1: Burpsuite is our go to for web apps.
Speaker 2: It's a Swiss army knife for web app testers. You
Speaker 2: can intercept traffic, modify requests, test for vulnerabilities like sequel injection,
Speaker 2: cross site scripting. It's incredibly powerful.
Speaker 1: It's like a hacker's playground.
Speaker 2: You could say that it allows for both automated and
Speaker 2: manual testing.
Speaker 1: So we've gathered our intel scanned the network and found
Speaker 1: some potential weaknesses. What's next in our penetration testing playbook, Well.
Speaker 2: Now comes the fun part, the drive. We try to
Speaker 2: turn those potential vulnerabilities into actual exploits.
Speaker 1: So we've reached the drive time to see if we
Speaker 1: can actually exploit the vulnerabilities we found.
Speaker 2: This is where things get real, right exactly.
Speaker 1: This is where all that intel and scanning pays off. Yeah,
Speaker 1: and when it comes to exploiting vulnerabilities, metasploit is the
Speaker 1: star of the show.
Speaker 2: Metasploy. Yeah, I've heard of that.
Speaker 1: It's incredibly powerful, almost like a library of pre built
Speaker 1: exploits for all sorts of vulnerabilities.
Speaker 2: Looks like having a cheat sheet for breaking into systems.
Speaker 1: Well not quite. The book stresses that it's not about
Speaker 1: blindly using the tool.
Speaker 2: Okay, so you need to know what you're doing. You
Speaker 2: really have to understand why exploits work, how those vulnerabilities
Speaker 2: can be manipulated. The book uses a classic example to
Speaker 2: illustrate this, the MS zero eight zero six seven vulnerability
Speaker 2: in Windows.
Speaker 1: Oh yeah, I remember hearing about that one. It was
Speaker 1: a big deal back in the day.
Speaker 2: It was. It shows how a tiny flow can have
Speaker 2: massive consequences. MSR eight zero six seven allowed attackers to
Speaker 2: run code on a vulnerable machine remotely, no authentication needed.
Speaker 1: Yikes. So you're saying someone could take control of a
Speaker 1: computer just by sending a network packet.
Speaker 2: That's the power of a remote code execution vulnerability. And
Speaker 2: metasploit has a module just for exploit msibeto zero six.
Speaker 1: Seven, So it takes care of all the technical bits.
Speaker 2: It helps craft the exploit, but you still need to
Speaker 2: understand what's happening under the hood.
Speaker 1: I see. So you need to know how to pick
Speaker 1: the right module, configure the settings, and choose.
Speaker 2: The payload exactly. The payload is the part that actually
Speaker 2: does the attacker's dirty work.
Speaker 1: What kind of dirty work It.
Speaker 2: Could be opening a command shell, giving full control of
Speaker 2: the system, or something more.
Speaker 1: Sneaky like installing a backdoor or stealing data exactly.
Speaker 2: It all depends on the attacker's goal.
Speaker 1: So metasploit helps exploit those vulnerabilities we found through scanning.
Speaker 1: What about those specific to web applications.
Speaker 2: That's where things get more hands on. The throw is
Speaker 2: all about manual web application testing.
Speaker 1: Ah, so we're getting into the art of penetration testing.
Speaker 2: Now you could say that it's about going beyond the
Speaker 2: automated tools and using your skills to find those hidden vulnerability.
Speaker 1: I like it. So we're talking SQL injection, cross site scripting,
Speaker 1: those kinds of things.
Speaker 2: You got it. Let's start with a SEQL injection or
Speaker 2: seql The book talks about tools like seql map and
Speaker 2: school Ninja.
Speaker 1: I've heard as a sql map, but what's school Inja.
Speaker 2: They both exploit SQL injection flaws, but they have different strengths.
Speaker 2: SQL injection is tricking an application into spelling secrets from
Speaker 2: its database.
Speaker 1: So like if I'm filling out a form online, someone
Speaker 1: could inject code to mess with the database.
Speaker 2: That's the idea. Sql map automates a lot of this.
Speaker 2: It tries different variations of SQL.
Speaker 1: Code, brute force approach.
Speaker 2: Kind of Now, school Ninja is more steallly.
Speaker 1: So it's designed to slip past security measures exactly.
Speaker 2: It's all about choosing the right tool for the job.
Speaker 2: The book gives some pretty cool examples of how to
Speaker 2: use these tools. Imagine retrieving user names and passwords from
Speaker 2: a database.
Speaker 1: Or even getting full control of the database server. That's
Speaker 1: a gold mine, right.
Speaker 2: It's like getting the keys to the kingdom.
Speaker 1: All right, so we've talked about SQL. What about cross
Speaker 1: site scripting. I know that's another big one, but how
Speaker 1: does it actually work.
Speaker 2: Cross site scripting or XSS, is injecting malicious code into
Speaker 2: a website, which then runs in the browser of other
Speaker 2: users who visit the site.
Speaker 1: So you're not attacking the server directly, not this.
Speaker 2: Time, you're targeting the people who use it. Think of
Speaker 2: it like planting a trap on the website.
Speaker 1: That's right.
Speaker 2: The book shows how to exploit EXSS vulnerabilities using a
Speaker 2: framework called BEEF, the Browser Exploitation Framework.
Speaker 1: BEEF sounds interesting.
Speaker 2: It basically gives you control over a victim's browser.
Speaker 1: Hold on, you're saying you can control someone else's browser.
Speaker 2: That's the power of XSS. Imagine you find a vulnerability.
Speaker 2: You could inject a link that, when clicked, loads this
Speaker 2: BEEF thing into their browser. Men, what then you can
Speaker 2: do all sorts of things like steal cookies, grab their
Speaker 2: logging credentials, even launch more attacks.
Speaker 1: WHOA, that's some serious stuff. Yeah, so you can basically
Speaker 1: do anything they can do on that website pretty much.
Speaker 2: The book even shows you how to use a BEEF
Speaker 2: module called petty Theft. It steals user credentials, proving just
Speaker 2: how dangerous EXSS can be.
Speaker 1: That's scary. So how do developers protect against this?
Speaker 2: Input valid is crucial Making sure any data submitted by
Speaker 2: users is carefully checked and cleaned. Think of it like
Speaker 2: having a security guard checking IDs at the.
Speaker 1: Door so no sneaky code gets through.
Speaker 2: Right now, we've talked about SQL injection and cross site scripting,
Speaker 2: let's move on to crosset request forgery or CSRF. AH.
Speaker 1: CSRF, that one always trips me up a little. It's
Speaker 1: a bit more subtle than the others, right it is.
Speaker 2: It exploits the trust a website has and a logged
Speaker 2: in user. Imagine you're logged into your bank's website. A
Speaker 2: CSRF attack could trick you into clicking a link, you
Speaker 2: kind of link, one that sends a hidden request to
Speaker 2: the bank doing something you didn't authorize.
Speaker 1: So like transferring money without me even knowing it exactly.
Speaker 2: And you don't even have to visit a shady website
Speaker 2: for this to happen. The link could be in an
Speaker 2: email or even on a legit website that's been compromised.
Speaker 1: That's unsettling. So how do you stop these CSRF attacks?
Speaker 2: CSRF tokens are a common defense, unique unpredictable tokens that
Speaker 2: the server generates and includes in every form you submit.
Speaker 2: It's like a secret handshake.
Speaker 1: So the server knows the request is legit.
Speaker 2: Exactly. It makes it much harder for attackers to forge
Speaker 2: those requests.
Speaker 1: Makes sense. Okay? What about session hijacking? I know that's
Speaker 1: another way attackers can impersonate users, right.
Speaker 2: Session hijacking is all about stealing those session tokens. They're
Speaker 2: like digital keys that websites use to keep you logged in.
Speaker 1: So if an attacker steals my second token they can
Speaker 1: log in is me.
Speaker 2: You got it. Tools like burpsuite can analyze how websites
Speaker 2: make these tokens looking for weaknesses.
Speaker 1: So what can developers do to make those tokens more secure?
Speaker 2: Make sure they're generated securely using random values and set
Speaker 2: them to expire after a short time. Also, storing them
Speaker 2: on the server side is much safer.
Speaker 1: Keep them out of reach of those attackers exactly.
Speaker 2: Okay, Now, how about something a bit more under the radar.
Speaker 2: Have you heard of fuzzing?
Speaker 1: Fuzzing rings a bell.
Speaker 2: It's a way of finding those hidden vulnerabilities by sending
Speaker 2: unexpected data to an application.
Speaker 1: So you're basically trying to break things by throwing random
Speaker 1: junk at them.
Speaker 2: There's a method to the madness. Fuzzing tools use lists
Speaker 2: of common inputs or generate them based on what they're testing.
Speaker 2: The book uses an example of fuzzing with burpsuite. Imagine
Speaker 2: testing an online store.
Speaker 1: Okay, I'm picturing it.
Speaker 2: You could fuzz the parameters that control things like product
Speaker 2: ideas or prices, and.
Speaker 1: By doing that you might find a way to, say,
Speaker 1: buy things for ridiculously cheap exactly.
Speaker 2: Fuzzing can uncover those weird vulnerabilities that other tests might miss.
Speaker 1: Cool. So we've covered a lot of offensive techniques so far.
Speaker 1: But let's say an attacker gets into a network. What's next?
Speaker 1: How do they move around and gain more access.
Speaker 2: That's where lateral movement comes in. It's all about moving
Speaker 2: from that initial foothold to other systems within the.
Speaker 1: Network, So escalating privileges getting to those crown.
Speaker 2: Jewels you got it, domain admin access is often the
Speaker 2: ultimate goal. The book goes over a bunch of tools
Speaker 2: and techniques for this, exploiting network protocols, using stolen credentials,
Speaker 2: even leveraging powerful scripting languages like PowerShell.
Speaker 1: Okay, let's break down some of these lateral movement techniques.
Speaker 1: The book mentions a tool called Responder. What's that all about?
Speaker 2: Responder is pretty clever. It exploits flaws in those protocols
Speaker 2: Windows uses for things like name resolution and finding proxies.
Speaker 2: Think LMNR, NBTNS and WPA.
Speaker 1: Okay, so it's taking advantage of how Windows networks work.
Speaker 2: It sets up a rogue server that tricks victims into
Speaker 2: connecting to it instead of the real one.
Speaker 1: So it's like a fake signpos point in them in
Speaker 1: the wrong direction.
Speaker 2: Exactly, and once they connect, bam, the attacker can grab
Speaker 2: all sorts of juicy information, NTLM hashes, cookies, you name it.
Speaker 1: Wait, those NTLM things are used for Windows logins, right
Speaker 1: they are.
Speaker 2: And Responder can snatch them right out of the air.
Speaker 2: Then you can use tools to crack those hashes and
Speaker 2: get the actual passwords. It's like getting a copy of
Speaker 2: the key to the castle.
Speaker 1: That's insane. So just by being on the same network
Speaker 1: you could potentially capture all that.
Speaker 2: It's surprisingly effective, especially when people are automatically logging into things,
Speaker 2: and Responder can do even more it can inject a
Speaker 2: fake wpad file, forcing the victim's browser to use the
Speaker 2: attacker's computer as a proxy.
Speaker 1: Talk about a man in the middle rat.
Speaker 2: You're controlling the traffic now. Another technique is smb relay attacks.
Speaker 2: They exploit how Windows handles authentication.
Speaker 1: Smb relay refresh my memory on that one.
Speaker 2: Imagine someone trying to connect to a file share with
Speaker 2: an smb relay attack. Their request goes through the attacker's
Speaker 2: machine first. Sneaky, the attacker relays the authentication request to
Speaker 2: the real file server, tricking the victim into giving their
Speaker 2: credentials to the attacker.
Speaker 1: So like a middleman intercepting the conversation exactly.
Speaker 2: Tools like smbu relay and invey are perfect for this
Speaker 2: kind of attack.
Speaker 1: Okay, so let's say we've snagged some of those NTLM
Speaker 1: hashes or other log in information. What then, how do
Speaker 1: we actually use those to get into other systems.
Speaker 2: That's where the big guns come out. Tools like WCE.
Speaker 1: And mimicat those names sound familiar.
Speaker 2: They extract passwords and hashes right from a computer's.
Speaker 1: Memory, so you could potentially dump the passwords of everyone
Speaker 1: logged onto a system.
Speaker 2: You got it, it's powerful stuff, but there's a catch.
Speaker 2: You usually need admin rights to use these tools.
Speaker 1: Makes sense you need some level of access first.
Speaker 2: That's often the whole point of lateral movement, to gain
Speaker 2: more and more control within the network, work your way
Speaker 2: up the ladder, so to speak. The book mentions a
Speaker 2: technique for exploiting group policy preferences.
Speaker 1: Group policy preferences, what's that?
Speaker 2: It's a Windows feature that admins use to manage settings
Speaker 2: across a whole network. The problem is the passwords for
Speaker 2: these policies can be stored insecurely, so.
Speaker 1: An attacker could potentially get their hands on some high level.
Speaker 2: Passwords domain admin credentials. Even that's game over. The book
Speaker 2: actually shows you how to do this using a Python
Speaker 2: script and tools.
Speaker 1: Like powersploy powersplay. Is that a PowerShell thing?
Speaker 2: It is? PowerShell is a scripting language built into Windows,
Speaker 2: and it's incredibly versatile.
Speaker 1: I've heard it's a favorite among both admins and attackers.
Speaker 2: For good reason. You can use it for automating tasks
Speaker 2: or carrying out sophisticated attacks.
Speaker 1: So it's powerful but also potentially dangerous if it falls
Speaker 1: into the wrong hands.
Speaker 2: Exactly. The book has a whole section on PowerShell for
Speaker 2: post exploitation, covering tools like power spoit and nicheing.
Speaker 1: What kind of things can you do with PowerShell after
Speaker 1: you've compromised the system?
Speaker 2: Oh, all sorts of things. You can inject toad into
Speaker 2: running processes, connect to other systems, even log keystrokes. The
Speaker 2: possibilities are endless.
Speaker 1: It's like a hacker Swiss army knife, you could say that.
Speaker 2: And because it's built into Windows, it often flies under
Speaker 2: the radar of security software.
Speaker 1: That makes it even more dangerous. So we've got lateral movement,
Speaker 1: privileged escalation, PowerShell. What other tricks do we need to
Speaker 1: be aware of?
Speaker 2: Well, no discussion of hacking would be complete without mentioning
Speaker 2: man in the middle attacks.
Speaker 1: Yep, manim attacks, Yeah, I've heard of those.
Speaker 2: This is where an attacker gets between two parties, intercept
Speaker 2: and potentially manipulating their communication so.
Speaker 1: They're easdropping and maybe even tampering with the messages exactly.
Speaker 2: And one of the classic tools for this is Ettercap.
Speaker 1: Ettercap that name sounds familiar.
Speaker 2: It lets you do ARP spoofing. It tricks devices on
Speaker 2: the network into sending their traffic through the attacker's computer.
Speaker 1: So the attacker becomes the middleman.
Speaker 2: Precisely, and they can do all sorts of nasty things.
Speaker 2: The book shows you how to use etter cap for
Speaker 2: DNS spoofing.
Speaker 1: DNS spoofing, what's that.
Speaker 2: Imagine you're trying to visit your bank's website with DNAs spoofing.
Speaker 2: The attacker redirects you to a fake website that looks
Speaker 2: just like the real deal.
Speaker 1: That's terrifying. You could easily enter your login info without
Speaker 1: realizing it's a trap.
Speaker 2: That's the danger. And it's not just websites. They could
Speaker 2: redirect you to fake update servers, download malware, you name it.
Speaker 1: Yikes. So edercap is a pretty powerful tool, it.
Speaker 2: Is, and there are even more advanced tools out there.
Speaker 2: The book mentions evil Foka, which targets IPv six networks at.
Speaker 1: Pv six that's the newer version of the Internet Protocol,
Speaker 1: right exactly.
Speaker 2: It just shows that attackers are always coming up with
Speaker 2: new ways to exploit new technologies.
Speaker 1: It's like an arms race. Speaking of new ways, what
Speaker 1: about attacks that target cookies? Those are used to track
Speaker 1: user sessions on websites right right.
Speaker 2: Cookies are little text files that websites store on your computer.
Speaker 2: They remember things like your login status or preferences.
Speaker 1: So if an attacker steals my cookies, they can basically
Speaker 1: become me on that website.
Speaker 2: You got it, And that's where attacks like sidejacking and
Speaker 2: cookie stealing come in.
Speaker 1: Tell me more about those.
Speaker 2: Sidejacking is all about capturing cookies over unencrypted connections. Say
Speaker 2: you're using public Wi Fi without a password.
Speaker 1: Uh, oh, I've done that.
Speaker 2: An attacker on that same network could use tools like
Speaker 2: Hamster or ferret to snag your cookies.
Speaker 1: And if they get my session cookie for like my
Speaker 1: online banking, they're in.
Speaker 2: They could potentially take over your account. That's why it's
Speaker 2: so important for websites to use HTTPS, which encrypts everything.
Speaker 1: So HTTPS scrambles it data, making it unreadable to snoopers.
Speaker 2: Makes sense? What about those tools I've heard of fire
Speaker 2: sheep and SSL strip. Didn't they mess with cookies and Https?
Speaker 2: They did. Fire sheep was notorious for hijacking sessions over
Speaker 2: those unencrypted networks, especially on sites like Facebook and Twitter, So.
Speaker 1: It showed everyone how vulnerable those unencrypted connections were.
Speaker 2: You could say that it was a wake up call.
Speaker 1: What about SSL strip? How does that work?
Speaker 2: Fsl strip is sneaky. It downgrades HTTPS connections to regular HTTP,
Speaker 2: removing that encryption.
Speaker 1: So even if a website uses HTTPS, an attacker could
Speaker 1: bypass it with SSL strip.
Speaker 2: In certain situations, yes, it allows them to eavesdrop on traffic,
Speaker 2: but they need to be in a position to manipulate
Speaker 2: that network traffic.
Speaker 1: So like running a fake Wi Fi hotspot.
Speaker 2: Or using a technique like ARP spoofing to readirect traffic.
Speaker 1: Okay, so we've covered a ton of network and web
Speaker 1: application attacks, but the book also talks about physical attacks
Speaker 1: the on sidekick.
Speaker 2: Right, security is often overlooked, but it's just as important
Speaker 2: as digital security. This section covers compromising wireless networks, cloning
Speaker 2: key cards, and planting secret devices for access.
Speaker 1: Let's start with those wireless attacks. How do people usually
Speaker 1: break into Wi Fi networks?
Speaker 2: If a company is still using WEP encryption, that's like
Speaker 2: leaving the door wide open. It's super easy to crack
Speaker 2: with tools like fern Wi Fi cracker.
Speaker 1: So if you see a Wi Fi network using WEP,
Speaker 1: run away fast.
Speaker 2: WPA two is the standard now much more secure, but
Speaker 2: even that can be vulnerable, especially if the passwords are weak.
Speaker 1: Right, A good password is your first line of.
Speaker 2: Defense absolutely to crack WPA two. Attackers usually capture the
Speaker 2: handshake when a device connects. Then they use tools like
Speaker 2: hashcat to try and figure out the password. That's why
Speaker 2: having a strong, unique password is so important.
Speaker 1: The longer and more random, the better. What about those
Speaker 1: WPS attacks I've heard of.
Speaker 2: WPS stands for a Wi Fi Protected setup. It was
Speaker 2: supposed to make connecting to Wi Fi easy, but it
Speaker 2: actually introduced some security flaws. It uses a pin, and
Speaker 2: attackers can route force those pins with tools like reaver
Speaker 2: root force, so.
Speaker 1: They just keep trying different pins until they get it.
Speaker 2: Pretty much, it's like trying every combination on the lock
Speaker 2: until it opens.
Speaker 1: Not very secure, then not at all.
Speaker 2: And the book covers even trickier wireless attacks like going
Speaker 2: after WPA enterprise networks.
Speaker 1: Those are the ones used in businesses right with stronger security.
Speaker 2: Exactly, they might try setting up a fake server that
Speaker 2: handles authentication. That way they can capture user names and passwords.
Speaker 1: Tricky, so they're impersonating the legitimate system exactly.
Speaker 2: It's all about deception.
Speaker 1: Okay, moving on to physical access. What are some sneaky
Speaker 1: ways attackers get into buildings or secure areas.
Speaker 2: Cloning those access cards is pretty common.
Speaker 1: You mean, like those key cards you swipe to get in.
Speaker 2: Yeah, they can copy the data from a legit card
Speaker 2: using an RFID reader and then create a fake one.
Speaker 2: It's like making a duplicate key so.
Speaker 1: You can walk right in. What about social engineering? Isn't
Speaker 1: that a big part of physical attacks?
Speaker 2: Huge They might trick employees into letting them in, pretend
Speaker 2: to be a delivery person, a maintenance worker, anything to
Speaker 2: get past security.
Speaker 1: So physical security is just as much about people as
Speaker 1: it is about technology.
Speaker 2: Totally. Now, the book gets even sneakier talking about planting,
Speaker 2: pen testing drop boxes.
Speaker 1: Drop boxes, what are those?
Speaker 2: They're tiny devices attackers hide inside the target's environment.
Speaker 1: Like a secret backdoor.
Speaker 2: You got it. They can be hidden anywhere air vents,
Speaker 2: behind furniture, even inside computers.
Speaker 1: So even if they lose their initial access, they still
Speaker 1: have a way.
Speaker 2: Back in exactly. The book mentions the odroid U two
Speaker 2: as a good platform for making these. They walk you
Speaker 2: through setting it up with remote access and scripts so
Speaker 2: the attacker can connect back in whenever they want.
Speaker 1: That's some next level stuff.
Speaker 2: It shows how determined some attackers can be. They'll go
Speaker 2: to great lengths to maintain access.
Speaker 1: Okay, we've covered a lot, from scanning networks to sneaking
Speaker 1: into buildings. What other must have skills do penetration testers need?
Speaker 2: The Hacker playbook calls these special teams things like cracking passwords,
Speaker 2: creating those exploits, and bypassing security measures.
Speaker 1: So the elite forces of hacking. Let's start with cracking passwords.
Speaker 1: What are some common techniques?
Speaker 2: Route forcing is the most basic. Trying every possible character
Speaker 2: combination until they find the right.
Speaker 1: Password sounds time consuming.
Speaker 2: It can be, especially for long, complex passwords, so attackers
Speaker 2: look for shortcuts, like what word lists and rules. Word
Speaker 2: lists are like dictionaries of common passwords. Rules are ways
Speaker 2: to modify those passwords.
Speaker 1: So they might take a password like password one two
Speaker 1: three and try variations like password one two three or
Speaker 1: p at two dollar and one two to.
Speaker 2: Three dollars exactly. They also use rules to add things
Speaker 2: like years or words related to the target. It's all
Speaker 2: about guessing based on how people usually create passwords.
Speaker 1: They're using psychology as much as technology.
Speaker 2: You got it, and they use tools like John the
Speaker 2: Ripple and hashcat to automate all this.
Speaker 1: What do those tools actually do?
Speaker 2: They take those stolen password hashes and try to guess
Speaker 2: the real passwords using word lists, rules, and various cracking techniques.
Speaker 2: It's a bit like a high tech guessing game.
Speaker 1: Okay, remind me again what's a hash password.
Speaker 2: It's like a scrambled version of a password. It's a
Speaker 2: one way transformation. You can't go back from the hash
Speaker 2: to the original password easily.
Speaker 1: So attackers are trying to find a password that, when hashed,
Speaker 1: matches the one they stole exactly.
Speaker 2: And the book shows how to crack MD five hashes
Speaker 2: using John the Ripper and WPA two hashes using hashcat.
Speaker 1: It all comes back to having strong, unique passwords and
Speaker 1: storing them securely.
Speaker 2: Absolutely, the stronger your passwords, the harder they are to crack.
Speaker 1: Okay, now let's talk about exploit development. How do attackers
Speaker 1: actually create those exploits?
Speaker 2: Yeah, that always seems like a mysterious process to me.
Speaker 1: It's a complex skill. It requires a deep understanding of
Speaker 1: software vulnerabilities and how to exploit them. Attackers often start
Speaker 1: by looking at known.
Speaker 2: Vulnerability so they do their research.
Speaker 1: They use websites like exploit dB and the National Vulnerability Database.
Speaker 1: They also use techniques like fuzzing, which we talked about
Speaker 1: and reverse engineering to find new ones.
Speaker 2: Whatt's reverse engineering.
Speaker 1: It's taking software apart to see how it works, like
Speaker 1: dissecting a machine to see how all the gears fit together.
Speaker 2: That sounds pretty intense.
Speaker 1: It can be. And once they find a weakness, they
Speaker 1: need to write code to exploit it, make it do
Speaker 1: things it wasn't designed to do.
Speaker 2: So it's like being a programmer, but for evil in
Speaker 2: a way.
Speaker 1: Yeah, but there are tools and frameworks that can help,
Speaker 1: like metasploit. Right, Okay, let's talk about bypassing security controls?
Speaker 1: How do attackers get past things like firewalls and anti virus.
Speaker 2: Attackers are always trying to stay ahead of the game.
Speaker 2: They might tunnel traffic through weird ports, disguise their code
Speaker 2: to avoid detection, even exploit flaws in the security software itself.
Speaker 1: It's a never ending battle, isn't it It is.
Speaker 2: Attackers and defenders are constantly trying to outsmart each other.
Speaker 2: That's why it's so important to stay up to date
Speaker 2: on the latest threats and have a layered security approach.
Speaker 2: Don't rely on just one thing to protect you.
Speaker 1: Okay, so we've covered a lot of the technical stuff,
Speaker 1: but what happens after a penetration test is done. What
Speaker 1: about the reporting phase?
Speaker 2: The report is super important. It's where you tell the
Speaker 2: client what you found and how they can improve their security.
Speaker 1: So it's not just about breaking in, it's about helping
Speaker 1: them fix things.
Speaker 2: Absolutely. A good report is clear, concise, and actionable. It
Speaker 2: tells them what's broken, how you broke it, and how
Speaker 2: to fix.
Speaker 1: It, so it's a roadmap to better security.
Speaker 2: Exactly. It should have an executive summary that gives a
Speaker 2: high level overview, then go into the nitty gritty of
Speaker 2: each vulnerability. How serious is it, how did you exploit it,
Speaker 2: and what can they do to fix it?
Speaker 1: So it's not just a laundry list of problems. It's
Speaker 1: about providing context and guidance.
Speaker 2: Right, and the report should prioritize the vulnerabilities based on
Speaker 2: their severity. It needs to offer concrete solutions, including technical
Speaker 2: details and best practices.
Speaker 1: What about the level of detail. Does it have to
Speaker 1: be super technical?
Speaker 2: It depends on who's reading it. For a tech team, yeah,
Speaker 2: go deep. But for management or executives, keep it simple
Speaker 2: and focus on the business impact of those vulnerabilities.
Speaker 1: So tailor the report to the audience.
Speaker 2: Exactly. A good penetration tester isn't just a tech whiz,
Speaker 2: they're also a good communicator.
Speaker 1: Communication is key in any field. Okay, so we've covered
Speaker 1: a ton of ground in this deep dive. Any major
Speaker 1: takeaways for our listeners.
Speaker 2: I think the biggest one is that penetration testing is
Speaker 2: crucial for finding and fixing security holes. It's not about
Speaker 2: being malicious, It's about helping organizations improve their defenses.
Speaker 1: And thinking like an attacker, understand their methods so we
Speaker 1: can build better defenses.
Speaker 2: You got it. And this book, The Hacker Playbook, is
Speaker 2: a great resource for anyone wanting to learn more about
Speaker 2: penetration testing.
Speaker 1: Definitely. Now imagine you're wrapping up a penetration test for
Speaker 1: that Fortune five hundred company. We talked about what would
Speaker 1: be the key points in your report.
Speaker 2: Well, it'd stressed the importance of a layered security.
Speaker 1: Approach, so don't rely on just one thing exactly.
Speaker 2: Multiple layers of security controls mean that if one fails,
Speaker 2: others are there to catch the attack, like having a
Speaker 2: backup plan for your backup plan. Defense in depth, right,
Speaker 2: and I'd emphasize strong passwords, keeping software up to date,
Speaker 2: and training employees on security best practices. You know the basics.
Speaker 1: The basics are often the most important.
Speaker 2: You'd be surprised how often they're overlooked. Of course, I'd
Speaker 2: also highlight those specific vulnerabilities we found during the test
Speaker 2: and how to fix them, so the.
Speaker 1: Report would act as a blueprint for improving their security.
Speaker 2: Precisely, give them the tools and knowledge to strengthen their defenses.
Speaker 1: Okay, so much great info today, any parting words of
Speaker 1: wisdom for our listeners.
Speaker 2: If you're interested in this stuff, definitely check out the
Speaker 2: Hacker Playbook. It's a fantastic resource.
Speaker 1: And remember, security is an ongoing journey. It's all about learning, adapting,
Speaker 1: and staying one step ahead.
Speaker 2: Well said. The more you understand about penetration testing, the
Speaker 2: better you can defend against those real world attacks.
Speaker 1: All right, let's end with a challenge for our listeners.
Speaker 1: How would you adapt these techniques for a specific type
Speaker 1: of organization like a hospital or a government agency. What
Speaker 1: would be different? Fascinating, right, all these different techniques and attacks.
Speaker 1: It's like a whole new world, it is.
Speaker 2: And as we've been diving into these network and web
Speaker 2: app attacks, it made me realize the book doesn't really
Speaker 2: cover one crucial area.
Speaker 1: I know, what you mean the cloud? With everything moving
Speaker 1: to the cloud these days, cloud security is a whole
Speaker 1: other ballgame.
Speaker 2: Right. It's like we've been focused on fortifying the castle,
Speaker 2: but now the battle's moving to the sky.
Speaker 1: How do you even approach a penetration test when your
Speaker 1: target is constantly shifting and changing in the cloud.
Speaker 2: That's a key difference with cloud penetration testing. You're not
Speaker 2: dealing with those physical servers and networks anymore.
Speaker 1: So it's not as simple as scanning ports and looking
Speaker 1: for open vulnerabilities.
Speaker 2: It's more about understanding the cloud architecture, the security models,
Speaker 2: how respond one's ability is shared between the cloud provider
Speaker 2: and the customer.
Speaker 1: So the rules of the game have changed exactly.
Speaker 2: Those traditional penetration testing techniques still apply, but you have
Speaker 2: to adapt them for the cloud.
Speaker 1: What kind of things do you have to consider?
Speaker 2: Oh, all sorts of things, misconfigured permissions, insecure APIs vulnerabilities,
Speaker 2: and those servillist functions.
Speaker 1: It's like learning a new language and a new set
Speaker 1: of combat skills all at once.
Speaker 2: You got it, and you have to be really careful
Speaker 2: about the legal and ethical side.
Speaker 1: Of things, right. You can't just go poking around on
Speaker 1: someone else's cloud without permission exactly.
Speaker 2: You need clear scope, coordination with everyone involved, and make
Speaker 2: sure you're operating within the rules and agreements.
Speaker 1: So cloud penetration testing requires a whole new level of expertise.
Speaker 2: It does, and it's a hot field right now. Lots
Speaker 2: of demand for skilled cloud pen testers.
Speaker 1: So for those listeners who are ready to take their
Speaker 1: skills to the cloud, what advice would you give them?
Speaker 2: First, get a solid grasp of those cloud technologies. Understand
Speaker 2: the different service models, like.
Speaker 1: What's the difference between infrastructure as a service, platform as
Speaker 1: a service, software as a service, all those as a
Speaker 1: service things exactly.
Speaker 2: Then dive into cloud security concepts, things like identity and
Speaker 2: access management, security groups, encryption. Learn about that shared responsibility.
Speaker 1: Model, knowing who's responsible for what right.
Speaker 2: Then start exploring cloud specific penetration testing tools and techniques.
Speaker 2: There are tools for scanning cloud infrastructure, testing APIs, finding holes,
Speaker 2: and serverleist functions. It's like upgrading your toolbox for the cloud.
Speaker 1: And don't forget those communication skills.
Speaker 2: You're right. Cloud penetration testing is often a team effort.
Speaker 2: You're working with the cloud provider, the client. Everyone needs
Speaker 2: to be on the same page, being able to clearly
Speaker 2: explain your findings is crucial.
Speaker 1: So if the Hacker Playbook is our guide to the
Speaker 1: on premises world, we need a whole new playbook for
Speaker 1: the cloud.
Speaker 2: I think that's a great way to put it. The
Speaker 2: fundamentals are still there about understanding how things work, finding
Speaker 2: those weaknesses, and showing how they can be exploited. But
Speaker 2: the cloud adds a whole new layer of complexity.
Speaker 1: And a whole new set of opportunities for those who
Speaker 1: are up for the challenge.
Speaker 2: Exactly.
Speaker 1: Well, on that note, I think it's time to wrap
Speaker 1: up this deep dive.
Speaker 2: Yeah, we covered a lot of ground.
Speaker 1: We explored the world of penetration testing, from setting up
Speaker 1: your own lab to uncovering those sneaky vulnerabilities in web
Speaker 1: applications and networks. We even ventured into the cloud and
Speaker 1: saw how the game is changing.
Speaker 2: It's been quite a journey.
Speaker 1: It has so to our listeners. Keep learning, keep experimenting,
Speaker 1: and keep pushing the boundaries of cybersecurity.
Speaker 2: Stay curious, stay ethical, and happy hacking.
Speaker 1: That's a wrap for this deep dive into the Hacker Playbook.
Speaker 2: Until next time, Stay safe out there in the digital
Speaker 2: world
Speaker 1: And keep those firewalls strong,