Speaker 1: Have you ever watched those intense movie scenes where a
Speaker 1: hacker types like furiously a few lines of code and poof,
Speaker 1: there's suddenly inside some top secret network happens exactly. It's
Speaker 1: it's definitely dramatic, but the reality of digital security, and
Speaker 1: you know, particularly the world of ethical hacking, it's, well,
Speaker 1: it's far more methodical and honestly, I think even more fascinating.
Speaker 2: I'd agree with that.
Speaker 1: Today we're taking a deep dive into Collie Linux, which is, well,
Speaker 1: it's really more than just an operating system, it really is.
Speaker 2: It's a comprehensive framework, a powerhouse you could.
Speaker 1: Say, yeah, packed with tools specifically designed for security auditing
Speaker 1: and what we call penetration testing testing app. So our
Speaker 1: mission for you, our listener, is to really extract the
Speaker 1: most important nuggets from a detailed guide to Callie Linux.
Speaker 1: Will explore exactly what penetration testing involves, right from the
Speaker 1: very start, from the initial intelligence gap all the way
Speaker 1: to that crucial final stage of reporting the findings. Think
Speaker 1: of this as your shortcut to truly understanding the sort
Speaker 1: of complex layers of digital defense and offense and offense. Yes,
Speaker 1: so let's unpack this. When we talk about calli linux.
Speaker 1: We're really talking about a complete framework.
Speaker 2: Yeah, it comes pre loaded an expansive set of tools
Speaker 2: covering well a huge range of cybersecurity use cases. Okay,
Speaker 2: what's truly impressive about Kalie Linux is its incredible adaptability.
Speaker 2: I mean, sure, you can install it on your personal laptop.
Speaker 1: Right the standard way, but it.
Speaker 2: Also excels on public servers for say, continuous network monitoring,
Speaker 2: or on dedicated workstations for really deep forensic analysis forensics. Okay,
Speaker 2: and here's where it gets particularly interesting. It can even
Speaker 2: run on tiny embedded devices, things with an arm architecture CPUs,
Speaker 2: like a Raspberry Pie.
Speaker 1: Wow, a Raspberry Pie. That's tiny.
Speaker 2: It is. Imagine that a device so small it could
Speaker 2: literally act as a time bomb in a wireless network.
Speaker 2: How so just by being plugged in somewhere discrete thanks
Speaker 2: to its low power consumption and you know, small size.
Speaker 2: It's about deploying powerful tools in completely unexpected places.
Speaker 1: That's a great point. So it's not just some fancy
Speaker 1: desktop environment. It's more like a like a Swiss army
Speaker 1: knife for cybersecurity pros exactly, and honestly, for anyone curious
Speaker 1: about how systems are secured.
Speaker 2: Or how they might be breach or breach.
Speaker 1: Yeah, so what kind of capabilities does the Swiss Army
Speaker 1: Knife actually have inside?
Speaker 2: Well beyond just the standard desktop cali Lenox offers this
Speaker 2: carefully selected suite of core capabilities. They really show its range. Okay, Now,
Speaker 2: instance information gathering. It gives you tools to systematically collect
Speaker 2: data on target.
Speaker 1: Systems, like what kind of data everything from.
Speaker 2: The hardware they use, the operating systems, the services active
Speaker 2: on their network, any sensitive areas that might be exposed,
Speaker 2: even details about their active directories.
Speaker 1: Active director Those are like the central control panels for
Speaker 1: big networks.
Speaker 2: Right verty much the central nervous system for managing users
Speaker 2: and resources and a large company network. Crucial information.
Speaker 1: And it's not just about what's inside a network, is it.
Speaker 1: It's also about what's visible from the outside.
Speaker 2: That's precisely where web application analysis becomes so critical. Ah okay.
Speaker 2: College's tools can pinpoint flaws loopholes in publicly available web applications,
Speaker 2: identifying them before malicious actors get a.
Speaker 1: Chance proactive defense exactly.
Speaker 2: Then there's vulnerability analysis. This uses tools loaded with massive
Speaker 2: databases to understand common weaknesses in local systems remote systems.
Speaker 2: It lets ethical hackers advise organizations precisely where they need
Speaker 2: to shore up their defenses.
Speaker 1: So you're essentially looking for those potential weaknesses, those open
Speaker 1: doors before the bad guys even spot them.
Speaker 2: That's the idea.
Speaker 1: What other kinds of doors can cally help test?
Speaker 2: Well? It also offers robust support for wireless attacks Wi
Speaker 2: Fi and stuff. Yeah, it lets you use multiple wireless
Speaker 2: cards to test and attack wireless networks. You can even
Speaker 2: uncover inactive roads or maybe switches that might be misconfigured.
Speaker 1: And getting pass logins, passwords.
Speaker 2: Absolutely, password attacks. It includes tools to crack passwords and
Speaker 2: attack what are called hashing systems.
Speaker 1: Hashing systems, right, they scramble the passwords.
Speaker 2: They do. They use mathematical functions to turn passwords into
Speaker 2: unique codes. Your password isn't stored directly, just its hash.
Speaker 2: Collie helps test how strong those hashing systems really are.
Speaker 1: That's a really clear explanation. But okay, what if all
Speaker 1: the technical defenses are like super strong, rock solid, where
Speaker 1: does a penetration tester look then?
Speaker 2: Ah, that leads us to social engineering tools. The human
Speaker 2: element exactly. Yeah, When the tech is solid, the human
Speaker 2: element often becomes the weakest link. COLLEIUE provides tools to
Speaker 2: exploit this, like what like crafting deceptive USD drives, you know,
Speaker 2: designed to entice someone to just plug it in, oh wow,
Speaker 2: or creating sophisticated fish websites that look exactly like legitimate
Speaker 2: banking sites for.
Speaker 1: Example, Tricking people.
Speaker 2: It's all designed to trick people into inadvertently compromising their
Speaker 2: organization's security. It's about understanding how human behavior can be leveraged.
Speaker 1: Okay, so when most people think about hacking, they probably picture,
Speaker 1: you know, that lone.
Speaker 2: Genius, Yeah, in a dark room.
Speaker 1: Frantically typing green codes, rolling up the screen and then.
Speaker 2: Bam, they're in instant access.
Speaker 1: Movies make it look so instant and chaotic, but true
Speaker 1: penetration testing it's actually incredibly structured, systematic, and surprisingly strategic.
Speaker 2: That's a crucial point. What's fascinating here is just how
Speaker 2: structured and methodical this entire process really is. It's worlds
Speaker 2: away from the chaotic hacking you see in films. Right,
Speaker 2: penetration testing follows a well a solid framework. It has
Speaker 2: a proper structure and a very defined sequence.
Speaker 1: Step by step, every.
Speaker 2: Single stage builds logically on the last one h decision
Speaker 2: is absolutely key. There are five main stages and they
Speaker 2: follow a very linear path, almost like a military operation,
Speaker 2: with distinct phases.
Speaker 1: So definitely no instant access. Then how does this methodical,
Speaker 1: almost intricate process actually start. What's the very first step.
Speaker 2: It all kicks off with something we call reconnaissance. Recon
Speaker 2: think of this like the military's intelligence analysts. It's all
Speaker 2: about passive information gathering ass Okay, imagine officers and analysts,
Speaker 2: you know, studying maps, monitoring activity from a secure, maybe
Speaker 2: dimly lit room, gathering insights without any direct engagement, no detection.
Speaker 1: So the goal is just learn everything.
Speaker 2: The primary goal here is to find out as much
Speaker 2: information about the target organization as humanly possible, all without
Speaker 2: them ever knowing.
Speaker 1: You're even looking, staying hidden, just observing. It's like casing
Speaker 1: a building from across the street.
Speaker 2: Perfect analogy.
Speaker 1: So once you've gathered all that passive intel, what's the
Speaker 1: next move? When you start getting a bit closer.
Speaker 2: That's when you move into scanning. Okay, now picture maybe
Speaker 2: a camouflaged soldier on a hilltop getting closer to the target,
Speaker 2: but still trying to stay undetected. Their goal is to
Speaker 2: confirm specific network infrastructure details. In pen testing, you use
Speaker 2: tools to fetch concrete information on the target systems, their computers,
Speaker 2: other devices on their network.
Speaker 1: It's active now, but still stealthy.
Speaker 2: It's stealthy as possible.
Speaker 1: Yes, And once you've pinpointed those vulnerabilities, gathered your intel
Speaker 1: from scanning, that's when you make your move, right.
Speaker 2: Yes, that's the exploitation phase.
Speaker 1: Okay, this sounds like the hacking part.
Speaker 2: This is akin to a covert entry team. Imagine soldiers
Speaker 2: entering a target camp through maybe a small gap in
Speaker 2: a fence or an open door. They gather vital intelligence
Speaker 2: and then crucially leave unnoticed.
Speaker 1: Get in, get info, get out clean Exactly.
Speaker 2: In our world, the goal is to enter the system,
Speaker 2: gain the necessary information, and then leave the system without
Speaker 2: being detected, all by leveraging those vulnerabilities you found earlier.
Speaker 1: But gaining acts us just once. That isn't always enough,
Speaker 1: is it, Especially if your objective requires you to come back,
Speaker 1: or maybe if a whole team needs access over time.
Speaker 2: Absolutely, that brings us to maintaining access. Okay, This is
Speaker 2: where you might think of, say, tunnel engineer. Tunnel engineer, Yeah,
Speaker 2: if they chart out a plan to get discrete tunnel
Speaker 2: to a specific room so they can easily maintain access
Speaker 2: to it. Ah, I see the strategic goal here is
Speaker 2: to significantly reduce the time and effort it would take
Speaker 2: to gain access to that same system again and again.
Speaker 2: Makes sense, whether it's for future tasks you need to
Speaker 2: perform or just for seamless collaboration among your pen testing team.
Speaker 2: Got it.
Speaker 1: And finally, after all that meticulous work, all those strategic steps,
Speaker 1: it's time for the communication part, translating the tech stuff precisely.
Speaker 2: The last stage is reporting. This is truly the commander's briefing.
Speaker 2: Imagine a commander presenting a detailed report to generals and admirals,
Speaker 2: clearly explaining the process they followed, the specific vulnerabilities they found,
Speaker 2: which systems were successfully.
Speaker 1: Attacked, so management can understand.
Speaker 2: It's about taking all that complex technical work and translating
Speaker 2: it into clear, actuable insights for management, for the technical
Speaker 2: teams so they can understand and crucially act upon it.
Speaker 1: That roadmap really paints a clear picture. Now let's maybe
Speaker 1: dig into the nitty gritty of some of these key
Speaker 1: stages and the tools involved. Okay, starting with reconnaissance again,
Speaker 1: what are some of the clever ways you gather info
Speaker 1: without you know, actually touching the target system directly.
Speaker 2: Well in reconnaissance. One powerful technique is website mirroring.
Speaker 1: Mirroring like making a copy exactly.
Speaker 2: Tools like rudge a get there's a command line tool
Speaker 2: they let you download an entire website, all its static
Speaker 2: HTML files, images, everything, locally to your machine.
Speaker 1: Why do that?
Speaker 2: It's not just for convenience, It's a critical stealth tactic.
Speaker 2: Think about casing that building again. You wouldn't keep knocking
Speaker 2: on the front.
Speaker 1: Door, right, Oh, definitely.
Speaker 2: Not Mirroring the site lets you meticulously analyze every detail,
Speaker 2: every hidden link, every piece of metadata, developer comments, all
Speaker 2: from your own machine without leaving a trace on their
Speaker 2: live servers.
Speaker 1: It's like taking the blueprint home to.
Speaker 2: Study precisely at your leisure.
Speaker 1: So you're creating a local replica. What about using something
Speaker 1: as common as say Google, I've heard of google hacking?
Speaker 1: Is that a rest.
Speaker 2: Absolutely Google hacking or Google dorking as it's sometimes called.
Speaker 2: It was pioneered by Johnny Long. It leverages advanced search
Speaker 2: parameters that go way beyond basic keywords, like how you
Speaker 2: can search for exact phrases, restrict searches to a specific
Speaker 2: site or domain like maybe only dogov domains. Or look
Speaker 2: for particular file.
Speaker 1: Types file types like word docs.
Speaker 2: Yeah or SQL files which might accidentally contain sensitive data
Speaker 2: like passwords if misconfigured, or PDF and docx documents that
Speaker 2: can hold internal information wow. For example, the Google Hacking Database,
Speaker 2: the GHDB has loads of these pre made queries. If
Speaker 2: a website is misconfigured, these queries could potentially reveal things
Speaker 2: like network device passwords, stuff that was never meant to
Speaker 2: be public.
Speaker 1: That's wild. It's almost like people leave clues just lying
Speaker 1: around online.
Speaker 2: Sometimes they do. It's about finding information that wasn't intended
Speaker 2: to be publicly discoverable.
Speaker 1: But what about the information they do willingly put out there,
Speaker 1: maybe without realizing the security implications exactly.
Speaker 2: And that's where social media and the human aspects become
Speaker 2: a genuine gold mine for a pen.
Speaker 1: Tester Like LinkedIn.
Speaker 2: LinkedIn is invaluable. You can map out organizational charts, figure
Speaker 2: out who does what. Even job postings can reveal technology insights,
Speaker 2: what systems they're using, what skills they're hiring. For interesting,
Speaker 2: there's even a concept called doppelganger creation, creating fictitious social
Speaker 2: media profiles to gather intelligence, though obviously you have to
Speaker 2: be extremely careful to op rate strictly within legal and
Speaker 2: ethical boundaries.
Speaker 1: There, right, a fixer key yeah, Okay. Beyond websites and
Speaker 1: social media, what about the Internet's own directory system DNS.
Speaker 2: Yeah, DNS attacks DNS.
Speaker 1: The Domain name system is basically the telephone directory of
Speaker 1: the Internet, right, translates website names into IP addresses. Tools
Speaker 1: like and slock up can reveal crucial info like a
Speaker 1: domain's mail servers MX records or it's name servers NS records. Okay,
Speaker 1: and the more powerful dig tool can even attempt what's
Speaker 1: called a zone.
Speaker 2: Transfer zone transfer.
Speaker 1: Yeah. If a name server is misconfigured, and sometimes they are,
Speaker 1: a zone transfer can effectively dump all the information it
Speaker 1: holds about a domain's network structure, like getting a full
Speaker 1: phone book for their entire internal system layout.
Speaker 2: Wow. Okay. So, once you've gathered all that passive intel
Speaker 2: through recon, it's time for scanning. How do you identify
Speaker 2: the more specific weaknesses active points of entry? Right? So, first,
Speaker 2: maybe a quick recap on some network fundamentals. Idea, think
Speaker 2: of a big building. It's got technically sixty five and
Speaker 2: thirty five doors for TCP communication and another sixty five, thousand,
Speaker 2: five and thirty five for UDP. These are ports.
Speaker 1: Ports are like doors got it.
Speaker 2: And firewalls are like the vigilant gate keepers deciding which
Speaker 2: doors are open or closed. Then you have the main
Speaker 2: it protocols. TCP is connection based, reliable, like a phone call.
Speaker 2: You establish a connection, confirm every message gets through using
Speaker 2: a three way.
Speaker 1: Handschick s yn sinac ack exactly.
Speaker 2: UDP is connectionless, faster, more like a radio broadcast. You
Speaker 2: just send info out, no confirmation it was received okay.
Speaker 2: And ICMP that's used for basic network health checks. Familiar
Speaker 2: commands like pie and trace route. They tell you if
Speaker 2: a device is online, how data packets get there.
Speaker 1: So with all those potential doors those ports, scanning is
Speaker 1: essentially knocking on them, seeing who answers and how.
Speaker 2: That's a perfect analogy. And the undisputed scanning king for this.
Speaker 1: Task is NMAP NMP right heard of it.
Speaker 2: It's incredibly powerful. Goes way beyond just detecting if a
Speaker 2: device is online. You can identify operating systems, the services
Speaker 2: running on open ports, sometimes even specific user accounts associated
Speaker 2: with those services.
Speaker 1: Wow, what are the different ways it knocks?
Speaker 2: Well? Key scan types vary in stealth and the info
Speaker 2: they give back. A stealth scan dash ASS tries an
Speaker 2: incomplete handshake. It's harder for poorly configured systems to log
Speaker 2: or detect sneaky. A TCP connect scan dash ST completes
Speaker 2: the handshake gives more detailed info, but it's much easier
Speaker 2: to detect. Then. You also have UDP SCANSSU for those
Speaker 2: UDP ports, and ACK scans SA, which can sometimes help
Speaker 2: figure out firewall rules.
Speaker 1: And you can control how fast or slow en MAP
Speaker 1: is how aggressive.
Speaker 2: Absolutely you can fine tune its behavior using timing templates.
Speaker 2: They range from T zero, which is paranoid extremely slow
Speaker 2: and stealthy all the way up to T five insane
Speaker 2: very fast but much more likely to be detected or
Speaker 2: even disrupt.
Speaker 1: Things, so you choose based on the situation exactly.
Speaker 2: You also have precise targeting methods, specifying IP ranges using
Speaker 2: CIDR notation, even feeding it lists of targets from a file,
Speaker 2: and you can select exact port selection WP if you
Speaker 2: only care about specific doors like webports or file sharing ports.
Speaker 1: And it has scripts too.
Speaker 2: Yes, a very powerful n MAP scripting engine NSSE. It
Speaker 2: allows you to run pre configured scripts for loads of
Speaker 2: automated checks, vulnerability detection, more information gathering. It's vital to
Speaker 2: keep that script database updated regularly. Script updated dub.
Speaker 1: That sounds like it could generate a lot of raw data.
Speaker 1: Is there a tool that helps make sense of it all?
Speaker 1: Tells you what vulnerabilities are actually present in a more
Speaker 1: digestible way.
Speaker 2: That's precisely where nessus comes in nessus Okay, it's a
Speaker 2: really powerful vulnerability scanner, comes from covie called tenable. Nessus
Speaker 2: excels at taking that raw scan data, analyzing it and
Speaker 2: identifying known vulnerabilities.
Speaker 1: How does it work?
Speaker 2: It typically has a web based interface, usually access securely
Speaker 2: over HTTPS on your local machine. This interface lets you
Speaker 2: easily configure scans, set of specific scanning policies, like maybe
Speaker 2: you only want to check for critical web vulnerabilities, and
Speaker 2: even disable certain.
Speaker 1: Checks like ones that might be too risky exactly like.
Speaker 2: Checks that might inadvertently trigger a denial of service derosis attack.
Speaker 2: If your rules of engagement for a specific test phibit
Speaker 2: potentially disruptive actions, you can disable those specific plugins in nessis.
Speaker 1: Okay, that makes sense. All right, So you've done recon
Speaker 1: You've scammed for vulnerabilities. Now we've arrived at stage three exploitation.
Speaker 1: We've covered a lot of ground finding weaknesses. Now it
Speaker 1: seems like the stage is set for the actual breach. Right.
Speaker 1: This is probably what most people think of when they
Speaker 1: hear hacking.
Speaker 2: It often is Yes, So what happens.
Speaker 1: Next in that process? And how do you even begin
Speaker 1: to categorize the ways you might get in?
Speaker 2: That's a great question, and it highlights an important distinction,
Speaker 2: the difference between an attack vector and an attack.
Speaker 1: Type vector versus type.
Speaker 2: Okay, think of it like a disease, a pathogen. The
Speaker 2: vector is the means by which it travels. For example,
Speaker 2: a web based attack vector means the attack comes through
Speaker 2: a web browser or web server interaction.
Speaker 1: Right the pathway.
Speaker 2: The type is the specific action the pathogen takes once
Speaker 2: it arrives. So for a web vector, the attack type
Speaker 2: might be something like SEQL injection manipulating database queries, or
Speaker 2: cross site scripting EXSS injecting malicious code into a website
Speaker 2: for other users to encounter. Ah.
Speaker 1: Okay, vector is the path. Type is the weapon.
Speaker 2: You got it. The vector is the path The type
Speaker 2: is the specific method of attack used on that path.
Speaker 1: So you're choosing your path then selecting your specific weapon
Speaker 1: for that path. Are there different kinds of exploits depending
Speaker 1: on how you're connecting to the target system itself.
Speaker 2: Yes. Broadly speaking, we categorize them as local exploits and remote.
Speaker 1: Exploits, local versus remote.
Speaker 2: A local exploit means you already have some level of
Speaker 2: access to the system, maybe physical access, or you've already
Speaker 2: logged in via SSH, or you're connected through a VPN.
Speaker 1: You're already inside somehow.
Speaker 2: Right, and social engineering often bridges this gap. Remember the
Speaker 2: USB drive. Yeah, tricking a user into running said trojan
Speaker 2: code embedded in a PDF or getting them to plug
Speaker 2: in that malicious USB drive left as a courier. Those
Speaker 2: actions can lead to the execution of code needed for
Speaker 2: a local exploit, okay. And remote remote to exploits, on
Speaker 2: the other hand, allow access purely through network connections. You
Speaker 2: don't need any prior physical presence or user interaction on
Speaker 2: the target machine itself. If it's not local, it's remote,
Speaker 2: you're attacking it across the network.
Speaker 1: Gotcha. And for actually doing these exploits, for orchestrating them,
Speaker 1: there's one tool that really stands out, isn't there the
Speaker 1: one you always hear about.
Speaker 2: Absolutely the Metasploitt framework Menness point. It's arguably one of
Speaker 2: the most powerful, most comprehensive tools available to a penetration tester.
Speaker 2: It's often considered the crown jewel of many toolkits.
Speaker 1: Why is it so powerful.
Speaker 2: It's a result of years of knowledge, countless tests and trials,
Speaker 2: contributions from security experts all over the globe. And it's incredibly.
Speaker 1: Modular, modular like build up blocks.
Speaker 2: Kind of think of it like James Bond's Aston Martin.
Speaker 2: It has all these different gadgets, right ejector seed oil slick.
Speaker 2: Metasploid is similar, with independent components or modules that can
Speaker 2: be swapped in and out depending on the mission.
Speaker 1: Okay, so it's not just one program, but a collection
Speaker 1: of specialized parts. What are the key parts?
Speaker 2: There are several key module types that work together. You
Speaker 2: have exploit modules. These contain the actual pre written code
Speaker 2: designed to leverage a specific vulnerability on a target system
Speaker 2: to gain.
Speaker 1: Access the attack code itself.
Speaker 2: Right. Then there are auxiliary modules. These are for tasks
Speaker 2: other than direct exploitation, things like scanning.
Speaker 1: Fuzzing, fuzzing, what's that sending lots.
Speaker 2: Of unexpected or random data to a program to see
Speaker 2: if it crashes or reveals vulnerabilities. Auxiliary modules also include
Speaker 2: things like SQL injection tools. They're mainly for gathering information
Speaker 2: or performing specific checks.
Speaker 1: Okay, exploits auxiliary what else?
Speaker 2: Payloads? Payloads are crucial. They are the instructions to the
Speaker 2: compromised system after it exploit succeeds. Think of them like
Speaker 2: tiny communication devices dropped on the target that tell it
Speaker 2: what to do next, like phone home exactly, or open
Speaker 2: a command prompt. Then you have listeners or handlers. These
Speaker 2: run on your machine waiting to communicate with those payloads
Speaker 2: once they'rerunning on the target, a receiving end precisely. And finally,
Speaker 2: shell code. This is the core, often very compact, piece
Speaker 2: of machine code within a payload that's directly responsible for, say,
Speaker 2: opening that command prompt or creating the communication channel. It's
Speaker 2: like the explosives packed inside the payload.
Speaker 1: Can you give us a more concrete example of how
Speaker 1: those payloads work what they let you do?
Speaker 2: Sure? Payloads are typically classified as either bind shells.
Speaker 1: Or reverse shells bind versus reverse.
Speaker 2: A bind shell is like a dormant program on the
Speaker 2: target system. It opens up a port and just waits
Speaker 2: for the attacker you to connect to it.
Speaker 1: Okay, it waits for your call right.
Speaker 2: A reverse shell, on the other hand, is often more useful,
Speaker 2: especially through firewalls. When it runs, it immediately connects back
Speaker 2: to the attacker's listening machine. It calls you exactly. It
Speaker 2: actively reaches out, often bypassing firewall rules that might block
Speaker 2: incoming connections. This gives the attacker direct keyboard access.
Speaker 1: And you mentioned a special shell.
Speaker 2: Min ah, Yes, the interpreter shell. This is really the
Speaker 2: bread butter of metasploit post exploitation. It's a special, highly
Speaker 2: versatile in memory shell. Once it's running on the target
Speaker 2: via a payload, it gives you its own small but
Speaker 2: powerful set of tools and commands directly on the compromise
Speaker 2: system without writing much to the disc, making it stealthier.
Speaker 1: So this is where it gets really interesting. Metasploit is
Speaker 1: like this finely tuned orchestra of hacking tools, each playing
Speaker 1: its part. How do you actually use it, say, to
Speaker 1: run a scan or launch an exploit?
Speaker 2: You can often access it via web based graphical interface,
Speaker 2: which can be easier for some tasks, or through its
Speaker 2: command line interface MS console, which is very powerful. Before
Speaker 2: any serious mission, it's crucial to update its database of
Speaker 2: exploits payloads and modules. Take it current always. When you're
Speaker 2: setting up a scan or configuring an exploit. Within metasploit,
Speaker 2: you define your targets, could be a single IP, arrange
Speaker 2: a list from a file. Then you can configure various
Speaker 2: advanced target settings like what this lets you fine tune things,
Speaker 2: maybe exclude certain sensitive addresses from the scan, add custom
Speaker 2: end map arguments for more specific scanning, or even set
Speaker 2: a custom TCP source port to try and bypass certain
Speaker 2: firewall rules that might filter based on source ports.
Speaker 1: Sneaky, And once you've successfully exploited a system, you get
Speaker 1: that interpreter session. What happens next? What can you actually
Speaker 1: do from there?
Speaker 2: Inside of interpreter session you unlock a whole suite of
Speaker 2: post exploitation capabilities. It's really powerful. You can collect system data,
Speaker 2: grab things like cash, Windows passwords, password hashes, or take
Speaker 2: screenshots of the user's desktop. Wow. You can access filesystem
Speaker 2: to upload your own tools, download sensitive files, or modify
Speaker 2: existing ones. You can get a standard command shell to
Speaker 2: interact directly with a target operating system using its native commands,
Speaker 2: so full control pretty close. You can also do more
Speaker 2: advanced things like great proxy pivot.
Speaker 1: Pivot What's that?
Speaker 2: It means using the compromised target machine as a gateway,
Speaker 2: you pivot through it to scan or attack other systems
Speaker 2: deeper inside their network you couldn't reach directly from the outside,
Speaker 2: like island hopping. Exactly like island hopping in a network.
Speaker 2: You can even create VPN pivot for encrypted traffic through
Speaker 2: the target, and of course you can terminate session cleanly
Speaker 2: when your work on that system is done.
Speaker 1: This all sounds very focused on networks and operating systems,
Speaker 1: But what about exploiting web servers and web applications? They're
Speaker 1: everywhere right, often publicly exposed.
Speaker 2: They are Web applications R and D a very common
Speaker 2: target precisely because of that public exposure. Things listed in
Speaker 2: the o.
Speaker 1: ASP Top test wellwash right Open Web Application Security Project.
Speaker 2: Yeah, their top ten lists the most common web vulnerabilities,
Speaker 2: things like injection attacks, SQL injection, command injection, broken authentication,
Speaker 2: cross site scripting XSS. These are frequent targets for PEN testers.
Speaker 1: So how do you test web apps? Is it similar?
Speaker 2: Web application testing often follows similar phases recon scanning, exploitation.
Speaker 2: It usually begins with a manual review.
Speaker 1: Manual justaing around.
Speaker 2: Pretty much meticulously clicking every link, trying default or common
Speaker 2: password guesses on log informs, carefully inspecting the website's htmail
Speaker 2: source code for any comments or hidden information left behind
Speaker 2: by developers. Good old fashioned.
Speaker 1: Detective work, finding clues.
Speaker 2: Finding clues. Then you move to fingerprinting. This uses tools
Speaker 2: to actively probe the web server to figure out what
Speaker 2: software it's.
Speaker 1: Running, like endmap, but for web servers sort of.
Speaker 2: Tools like netcat NC can connect to the web server's port,
Speaker 2: and by setting a simple head HTTP one point zero request,
Speaker 2: you can often get backheaders revealing valuable info like it's
Speaker 2: running apatche version two point two on Linux of boontu okay.
Speaker 2: Other tools like telnet can do similar things, and SSL
Speaker 2: scan is great for checking which versions of ssltls the
Speaker 2: server supports and looking at its certificate details for potential weaknesses.
Speaker 1: And then automated tools.
Speaker 2: Yes, after manual checks and fingerprinting, automated scanning tools come
Speaker 2: into play. There are several good ones in colli Aracne
Speaker 2: has a nice WebUI and is good for scanning a
Speaker 2: single host I port W three AF was developed by
Speaker 2: Owas people. It's very comprehensive with lots of plugins for
Speaker 2: different checks and websploit is a Ruby based tool focused
Speaker 2: specifically on web app exploits, and it integrates nicely with metasploit.
Speaker 1: Okay, so a whole suite for web stuff too. Now,
Speaker 1: after all that effort to gain access through the network
Speaker 1: through web app whatever, the next stage you mentioned was
Speaker 1: maintaining access the long game. Why is it so crucial
Speaker 1: to establish that persistent access once you're in It seems
Speaker 1: like you've already done the hard part.
Speaker 2: The purpose is actually quite straightforward. It's to reduce the
Speaker 2: time and effort taken to gain access to the same
Speaker 2: system again.
Speaker 1: Later on efficiency, efficiency.
Speaker 2: Exactly, and for collaboration. If you have an ethical hacking
Speaker 2: team working on an engagement, you definitely don't want every
Speaker 2: single team member to have to go through the entire
Speaker 2: potentially complex exploitation process from scratch every time they need
Speaker 2: to access a system that's already been compromised by a teammate, right, That.
Speaker 1: Would be a huge waste of time.
Speaker 2: It's about efficiency and enabling sustained engagement, whether for further
Speaker 2: testing or coordinated team actions.
Speaker 1: So you leave a little something behind a way back in.
Speaker 2: You might, yeah, and understand this properly. We need to
Speaker 2: clarify some terminology first, Okay. Malware is just a generic
Speaker 2: umbrella term for any kind of malicious software viruses, worms, trojans,
Speaker 2: et cetera.
Speaker 1: Got it.
Speaker 2: A backdoor is a program specifically planted on a system
Speaker 2: after initial compromise. Its sole purpose is to provide easy
Speaker 2: future entry bypassing the original exploit method the secret entrance exactly.
Speaker 2: A trojan horse is software that looks legitimate or useful,
Speaker 2: maybe a game, a utility, a PDF read, but secretly
Speaker 2: contains hidden malicious functionality like that back door. Very A
Speaker 2: virus typically infects existing legitimate files or processes on the system.
Speaker 2: Worms are self multiplying malware that spread across networks, generally
Speaker 2: something you strictly avoid in a real ethical penetration test
Speaker 2: because they can quickly get out of control and cause
Speaker 2: widespread damage.
Speaker 1: Right too risky, definitely.
Speaker 2: Keyloggers are tools that capture keystrokes with the user types,
Speaker 2: and botnets are networks of compromised computers, all controlled remotely
Speaker 2: by a botmaster for coordinated tasks like sending spam or
Speaker 2: launching denial of service attacks.
Speaker 1: Okay, that clarifies the term. So what are some of
Speaker 1: the actual strategies for maintaining this access once you've decided
Speaker 1: you need it well.
Speaker 2: Strategies can include things like collocation. This might mean hosting
Speaker 2: malicious services on remote servers you control, or sometimes even
Speaker 2: using compromised user computers as part of a larger infrastructure
Speaker 2: like that spamming botnet.
Speaker 1: Example, using their resources right.
Speaker 2: Remote communications are key setting up covert tunnels, maybe using
Speaker 2: VPNs or enabling remote desktop access back into the compromise system.
Speaker 2: And command and control C two or C and C
Speaker 2: systems are the infrastructure used by attackers to send commands
Speaker 2: to and receive data from those compromise systems, managing their
Speaker 2: back doors or.
Speaker 1: Bots can metasploit help with creating and managing these backdoors too.
Speaker 1: It seems like it does everything.
Speaker 2: It's incredibly versatile for this as well. Metaploid has tools
Speaker 2: like ms venom now which combined older tools like apps
Speaker 2: payload and ansome code specifically for generating executable files payloads
Speaker 2: for various operating systems, architectures and formats.
Speaker 1: So you can make a Windows backdoor a Linux one exactly.
Speaker 2: And what's more, you can often encode these payloads. Encoding
Speaker 2: tries to obfuscate the payloads signature to make it harder
Speaker 2: for antivirus software to detect it as malicious, avoiding av
Speaker 2: trying to Yes, it's an ongoing cat and mouse game.
Speaker 2: For example, using metasploid, you could create a trojan horse
Speaker 2: by taking a legitimate harmless program like the standard Windows
Speaker 2: calculator Yeah calc dot ex and embedding one of these
Speaker 2: encoded backdoor payloads inside it. When the user runs the calculator,
Speaker 2: the back door runs silently in the background.
Speaker 1: Wow. Sneaky. So you create and deploy that back door
Speaker 1: maybe hidden in a trojan than what how do you
Speaker 1: actually connect to it later?
Speaker 2: You absolutely need to set up a metasploil listener on
Speaker 2: your attacking machine. This is a critical step the receiving
Speaker 2: end again right. The listener uses the exploit multi handler
Speaker 2: module in metasploit. You can figure it with the same
Speaker 2: payload type, IP address LA to a plate and port
Speaker 2: out or that you use when you generated the back door.
Speaker 2: It then waits patiently listening for an income and connection.
Speaker 1: And when the back door runs.
Speaker 2: When the back door executable runs on the target machine,
Speaker 2: it calls back to the IP address and port where
Speaker 2: your listener is waiting. The listener catches the connection and boom.
Speaker 2: You usually get a interpreter session giving you control again.
Speaker 1: But what about reboots? If the user restarts their computer,
Speaker 1: is the back door gone?
Speaker 2: Good question. Simple backdoors might not survive a reboot. That's
Speaker 2: where persistent back doors come in. Interpreter itself has scripts
Speaker 2: like persistence or older ones like schedule EMA, which can
Speaker 2: help establish access that persists over time out they might
Speaker 2: install the back door as a service, or create scheduled
Speaker 2: tasks or add registry keys so that the back door
Speaker 2: automatically runs again every time the system boots up or
Speaker 2: when a user logs in, even on a regular schedule
Speaker 2: like daily or weekly. This ensures ongoing access.
Speaker 1: Clever and what about capturing sensitive information like passwords? Can
Speaker 1: you do that once you have this sustained access.
Speaker 2: Yes. Metasploit's Interpreter shell includes a powerful built in key logger,
Speaker 2: capturing typing exactly within an active interpreter session. Simple commands
Speaker 2: allow you to start it, keys can start, retrieve everything
Speaker 2: the user has typed since you started it, keyscin dump
Speaker 2: and then stop it keyskin.
Speaker 1: Stop So you could potentially grab passwords as they.
Speaker 2: Type them, potentially yes or other sensitive information typed into
Speaker 2: the emails, documents, anything. It's a very effective way to
Speaker 2: collect information, although again the ethical considerations in the specific
Speaker 2: rules of engagement for a test are absolutely paramount here.
Speaker 2: You only collect what's necessary and authorized.
Speaker 1: Right, Absolutely, So, all this meticulous work, recon scanning, exploitation,
Speaker 1: maintaining access, all these strategic steps, these powerful tools, it
Speaker 1: all culminates in the final and as you said, arguably
Speaker 1: most sortant stage reporting. This is where you translate all
Speaker 1: those technical findings into the so what for the people
Speaker 1: who actually need to act on it?
Speaker 2: Right? Exactly right? Yeah, If we connect this back to
Speaker 2: the bigger picture, the entire penetration testing life cycle, from
Speaker 2: that initial passive observation right through to securing ongoing access,
Speaker 2: it all leads to this final, sometimes overlooked but utterly
Speaker 2: crucial step, clear actionable reporting. Because without it, Without it,
Speaker 2: all the brilliant technical work is frankly just academic, it
Speaker 2: doesn't help the organization improve its security. These reports are
Speaker 2: absolutely vital for both management, who need to understand the
Speaker 2: risks and allocate resources, and for the technical staff who
Speaker 2: need the details to actually fix the vulnerabilities.
Speaker 1: What are the key parts of a really good penetration
Speaker 1: test report? What should be in there?
Speaker 2: Well, standard reports usually include several key sections. The executive
Speaker 2: summary is critical. It's a high level overview, usually no
Speaker 2: more than maybe two or three paragraphs, exactly written last
Speaker 2: designed to quickly convey the most critical findings and the
Speaker 2: overall security posture to non technical management needs visuals maybe graphskay?
Speaker 1: What else?
Speaker 2: And there's the engagement procedure section. This details the scope
Speaker 2: of the test, what was in scope, what was out
Speaker 2: of scope, the agreed upon methodology, any limitations. Transparency is key.
Speaker 2: An optional architecture and composition section might describe the target
Speaker 2: environment operating systems, key hardware, network layout if relevant, then
Speaker 2: the juicy stuff, then the core. The finding section. This
Speaker 2: lists all the discovered vulnerabilities, usually ranked by severity critical, high, medium, low. Crucially,
Speaker 2: these should be clearly explained, demonstrate how they were exploited
Speaker 2: and ideally linked to potential business impact or relevant compliance
Speaker 2: standards like PCIDSS for payment cards or FISMA for government systems.
Speaker 1: Okay, and just finding problems isn't.
Speaker 2: Enough, No, you need recommended actions. This section outlines practical
Speaker 2: steps the organization can take to remediate each finding or
Speaker 2: at least mitigate the risk general fixes, configuration changes, patching advice.
Speaker 2: Then a conclusion that summarizes the engagement and re emphasizes
Speaker 2: the most critical findings, and finally appendices. This is where
Speaker 2: you put supporting technical details raw TOUOL outputs, screenshots, scripts used,
Speaker 2: IP addresses tested, anything that backs up the findings.
Speaker 1: How important is the sort of professionalism the delivery of these.
Speaker 2: Findings extremely important. Professionalism is absolutely key. You need to
Speaker 2: avoid accusatory language or blaming individuals, focus purely on the
Speaker 2: objective facts that technical findings and the associated risks. Just
Speaker 2: the facts, Just the facts, and ensure secure delivery. These
Speaker 2: reports contain highly sensitive information about an organization's weaknesses. You
Speaker 2: need secure methods for handing them over in careful recordkeeping.
Speaker 1: And what happens to the reports afterwards. You don't just
Speaker 1: leave them lying.
Speaker 2: Around, definitely not. Secure storage is critical. Encrypted digital copies
Speaker 2: may be stored on offline media, protected with strong passwords, or,
Speaker 2: depending on the agreement and legal advice, complete deletion might
Speaker 2: be required after a certain period. Sometimes this requires two
Speaker 2: person integrity, meaning to authorized individuals must concur before deletion
Speaker 2: can occur. Always follow legal counsel's advice on retention.
Speaker 1: And deletion handle with extreme care. Are there tools within
Speaker 1: Kalie itself to help with this reporting process? It sounds
Speaker 1: like a lot to compile.
Speaker 2: Yes, Collie does offer tools specifically designed to streamline reporting.
Speaker 2: Dratis is a popular open source framework. It's great for
Speaker 2: collaboration within a testing team and helps consolidate findings and
Speaker 2: evidence from various tools into a central repository, making report
Speaker 2: generation easier. Another useful one sometimes mentioned is Magic Tree.
Speaker 2: It's designed for data management and reporting, organizing information in
Speaker 2: a hierarchical tree structure, which can be helpful for structuring
Speaker 2: complex findings and notes during an engagement, ready for compiling
Speaker 2: into the final report.
Speaker 1: So tools to help manage the evidence and build the report. Okay,
Speaker 1: So there you have it. We've taken a pretty comprehensive
Speaker 1: deep dive, haven't we. We certainly have into the world
Speaker 1: of Kalie, Linux and the intricate art of penetration testing.
Speaker 1: We've moved from those high level concepts right down to
Speaker 1: specific tools and the very methodical techniques they employ.
Speaker 2: From recon all the way to reporting exactly.
Speaker 1: Our mission today was really to give you our listener
Speaker 1: a shortcut, a way to be truly well informed about
Speaker 1: the systematic, often complex nature of securing digital systems. From
Speaker 1: that initial passive reconnaissance, through active scanning and exploitation that
Speaker 1: may be maintaining persistent access, and finally that absolutely crucial
Speaker 1: step of clear, actionable reporting.
Speaker 2: It's definitely a detailed, strategic process.
Speaker 1: Far beyond what you typically see in the movies, that's
Speaker 1: for sure, miles away. And as you reflect on the
Speaker 1: incredible depth and frankly sophistication of these tools and techniques,
Speaker 1: and the fact that technology is just constantly evolving, maybe
Speaker 1: consider this, what does true digital security even look like,
Speaker 1: especially in a world where we're constantly connecting new smart devices, watches, fridges, cars,
Speaker 1: expanding our digital footprint in ways we're only just beginning
Speaker 1: to fully grasp.
Speaker 2: That's a big question, it is.
Speaker 1: And how might you apply this newfound understanding, even just
Speaker 1: a little bit to protect your own corner of that
Speaker 1: digital world.