In this lesson, you’ll learn about:
You can listen and download our episodes for free on more than 10 different platforms:
https://linktr.ee/cybercode_academy
- The top real-world network threats and how to think like an attacker
- The full process of conducting a vulnerability assessment
- Tools and methodologies used in modern vulnerability scanning
- How penetration testing works and its legal, ethical, and operational requirements
- Red team vs. blue team roles
- Best practices for reporting and mitigating discovered vulnerabilities
- Defense is inherently harder than offense, so defenders must understand attacker mindset and methodology.
- Understanding how attacks work is essential for proper mitigation.
- A widely referenced list (e.g., from firms like Netrix) highlights the most common network attacks, including:
- Denial-of-Service (DoS)
- Man-in-the-Middle
- Phishing and spear phishing
- Drive-by attacks
- Password attacks
- SQL injection
- Cross-Site Scripting (XSS), CSRF/XSURF variants
- Eavesdropping
- Birthday attacks
- Malware attacks
- A structured evaluation of security policies, controls, and system configurations.
- A combination of automated scanning and manual analysis.
- Verifies whether an organization’s defenses align with its intended security posture.
- Network Discovery
- Use tools like Nmap or Zenmap to map the environment.
- Identify open ports, services, and protocols.
- Establish scope and baseline information.
- Vulnerability Scanning
- Dedicated scanners identify known vulnerabilities in devices and applications.
- Examples commonly used in labs or controlled learning environments include:
- Nessus
- OpenVAS
- Aunetis
- Application-level scanners include:
- Burp Suite
- Nikto
- Wapiti
- SQLMap
- Many tools are pre-packaged in specialized security testing operating systems (e.g., Kali Linux, Parrot OS).
- Analyzing and Validating Results
- Remove false positives.
- Evaluate severity and risk.
- Determine potential impact and remediation urgency.
- Simulates real-world attacks to evaluate the organization's true security posture.
- Helps validate defenses, identify exploitable paths, and strengthen systems.
- Specialized security operating systems like Kali Linux and Parrot OS.
- Frameworks such as Metasploit provide structured exploit testing in controlled environments.
- White Box: Full internal knowledge (IP ranges, architecture, credentials).
- Black Box: No prior knowledge, simulating an external attacker.
- Gray Box: Partial information, simulating an insider or semi-informed adversary.
- Red Team: Offensive testers simulating adversaries.
- Blue Team: Defensive personnel monitoring, detecting, and mitigating attacks.
- A formal contract must define:
- Scope of testing
- Rules of engagement
- Permission to perform active tests
- Ensures compliance with laws (such as the CFAA in the U.S.) and protects testers from liability.
- A structured professional report including:
- Executive summary
- Risk-ranked list of vulnerabilities
- Technical analysis and reproduction details
- Clear mitigation recommendations for the security team
You can listen and download our episodes for free on more than 10 different platforms:
https://linktr.ee/cybercode_academy
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
You know, when you think about jobs in tech, network
security has to be one of the most uh just
incredibly stressful fields out there.
Speaker 2 (00:08):
Oh without attack, because.
Speaker 1 (00:09):
If you're the one defending a network, you have to
be right one hundred percent of the time. You're securing
this massive perimeter against every single possible angle.
Speaker 2 (00:19):
Of attack, every single one.
Speaker 1 (00:20):
But the malicious attacker they only need to find one
vulnerable window, one tiny crack in the armor, and they've succeeded.
Speaker 2 (00:30):
That's the fundamental asymmetry of it.
Speaker 1 (00:32):
It really is. Playing defense is just inherently harder than
playing offense in the digital world. Okay, let's unpack this.
If defense is so you know, inherently difficult, what is
the most successful security strategy you can adopt?
Speaker 2 (00:45):
Well, it's a bit ironic.
Speaker 1 (00:47):
Really, the answer is to stop playing defense altogether and
just switch sides exactly.
Speaker 2 (00:52):
The most effective security strategy is taking a proactive offensive approach, thinking.
Speaker 1 (00:56):
Exactly like an attacker would about your own network.
Speaker 2 (00:59):
You have to learn how to break your own system
before someone else does.
Speaker 1 (01:02):
So that's what this is all about.
Speaker 2 (01:04):
That is precisely the mission for this deem dive. You
you can't manage or secure what you haven't thoroughly tested.
We are going beyond the theory today. We're going to
discuss the three pillars of modern network defense. First, how
to understand the threat landscape, then how organizations find their
own weaknesses, and finally how they actually simulate live attacks
(01:25):
to stay secure.
Speaker 1 (01:26):
So let's start there with the offensive mindset the threat landscape.
We have to face a pretty hard truth that INFOSEC
experts lay out all the time. And what's that an
organization can spend I mean an unlimited amount of money
trying to secure their environment and still not guarantee you
one hundred percent prevention of an outside attack.
Speaker 2 (01:46):
It's impossible. So mitigation and just deeply understanding the enemy's
playbook become absolutely key.
Speaker 1 (01:52):
It's the foundation, right it is.
Speaker 2 (01:54):
If you don't know the playbook, you can't defend the goal.
So instead of listing every single attack method out there,
it's more useful for you to think about them in categories. Okay,
and we really see three major categories dominating in the
real world. First, you have social engineering.
Speaker 1 (02:08):
Attacks the human element exactly.
Speaker 2 (02:11):
These target human weakness. The biggest players here are phishing
and spear phishing, you know, tricking users into giving up
credentials and what else falls in that bucket, And the
more passive eavesdropping attack where an attacker is just listening
to network traffic or data as it's being transmitted.
Speaker 1 (02:28):
Social engineering just feels, i don't know, cheap and easy
for the attacker to deploy it is, which.
Speaker 2 (02:33):
Makes it incredibly common. So the next category is what
i'd call disruption and access attacks. Okay, these are all
about brute force or interception. This includes the denial of
service or DOSS attack.
Speaker 1 (02:46):
Where the goal is just to overwhelm the system so
it crashes YEP, and.
Speaker 2 (02:51):
The Man in the middle or MITM attack, which involves
intercepting and maybe even altering communication between two parties without
them knowing.
Speaker 1 (02:59):
So what about the technical attacks, the ones that go
after the code itself.
Speaker 2 (03:03):
That's the third category, application flaws and exploitation. These attacks
hit directly at weaknesses in software, especially custom web applications.
Speaker 1 (03:12):
The classic examples.
Speaker 2 (03:13):
The classics SQL injection, where malicious SQL queries are put
into input fields to corrupt or expose the database, and
cross size scripting or EXSS.
Speaker 1 (03:25):
Right, where unauthorized code gets run through a trusted website.
Speaker 2 (03:28):
Because the site didn't properly validate its inputs. If you
understand those three categories, you're already in a much much
better place to deploy countermeasures.
Speaker 1 (03:36):
Which brings us to the next crucial step. Knowing the
list of threats is step one. But how do you
actually prove your network is secured against them? You can't
just assume your firewall is working. You have to test
it regularly.
Speaker 2 (03:48):
And this is where we transition from understanding threats to
proactive self examination. This is the realm of the vulnerability assessment.
Speaker 1 (03:57):
So what is that exec At.
Speaker 2 (03:59):
Its core, assessment is a rigorous, in depth examination of
an organization's IT security policies, it's infrastructure, it's procedures. You're
evaluating everything against the risks the company.
Speaker 1 (04:10):
Faces, and the main purpose is just to find the
weak spots.
Speaker 2 (04:13):
It is to uncover information about known weaknesses in your
current security controls.
Speaker 1 (04:17):
So does this rely on one method or is it
more of a mix.
Speaker 2 (04:21):
It's a mix. It involves both automated tools running on
scripts and manual testing where an expert actually tries to
find the holes that a machine might have missed.
Speaker 1 (04:31):
So where you start.
Speaker 2 (04:32):
The first typical step is running a network discovery scan
just to define the scope to see what systems are
even on the network. A decades old but still wildly
popular tool for this is NMAP, the Network Mapper. It's
fantastic for finding out what devices exist and what ports
and protocols they're using.
Speaker 1 (04:51):
NMP. That sounds like a pretty hardcore command line tool,
right it can be.
Speaker 2 (04:55):
Yeah, it's incredibly powerful.
Speaker 1 (04:57):
So for someone just starting out trying to learn this,
is there an easier way in?
Speaker 2 (05:02):
Oh? Absolutely, that's the beauty of NMAP. It has a
user friendly graphical interface version called zenmap. Oh okay, and
it basically gives you training wheels while you're learning how
to properly craft and generate the NMAP commands. In the background,
it's a great way to visualize the network.
Speaker 1 (05:17):
Got it? So, once that initial scam is done, what's next?
Speaker 2 (05:21):
Then we move to advanced vulnerability scanning. These specialized scanners
go beyond just finding open ports. They actively check systems
and applications for known vulnerabilities, flaws.
Speaker 1 (05:34):
That have already been documented and you know, supposedly patched exactly.
Speaker 2 (05:37):
The two primary industry names to know here are nessis
and open VAS.
Speaker 1 (05:42):
And I imagine the assessment doesn't stop at the network level. Right,
especially for companies running their own custom software, the application
is often the easiest point of entry.
Speaker 2 (05:51):
That's spot on. For proprietary code, we need tools for
specific application analysis. If you're testing a web application, tools
like burpsuite are essential for checking common web flaws.
Speaker 1 (06:02):
And what about that SQL injection we mentioned.
Speaker 2 (06:04):
For that, you do something like sql map, which is
used specifically for automatically testing for those really dangerous SQL
injection vulnerabilities.
Speaker 1 (06:12):
Here's where it gets really interesting. If you're a cybersecurity
professional or say a student, looking to practice with these
tools ethically, you don't have to download twenty different programs
and install them one by one.
Speaker 2 (06:24):
No, that would be a nightmare, and that's a key
piece of practical advice. The vast majority of these professional
testing tools are all conveniently consolidated into specialized Linux.
Speaker 1 (06:35):
Distributions like Callie Linux.
Speaker 2 (06:37):
Cali Linux, or Parados. Those are the big two. My
advice is always to download one of those and run
inside a virtual machine a VM. Yeah, that way you
can practice with real world applications in a safe, sandboxed
environment without messing up your main operating system.
Speaker 1 (06:53):
Okay, so running a vulnerability assessment gives you a checklist,
a list of known weaknesses. But that checklist just tells
you there might be.
Speaker 2 (07:00):
A hole, right, It doesn't prove it.
Speaker 1 (07:03):
So how do you know if those weaknesses are actually exploitable.
That's what takes us to the third most advanced stage,
active testing.
Speaker 2 (07:11):
That is the definition of penetration testing or pen testing.
This is the next level after a simple assessment. We
aren't just finding vulnerabilities anywhere.
Speaker 1 (07:19):
It's actively trying to exploit them.
Speaker 2 (07:21):
We are actively trying to exploit them in a controlled
ethical environment to prove the whole exists and to demonstrate
the actual risk to the organization. This is often called
white hat hacking.
Speaker 1 (07:33):
When you say white hat, you're making a distinction between
the good guys and the bad guys.
Speaker 2 (07:37):
Precisely, we have to be clear about the moral spectrum here.
The term itself came from old Western movies. Believe it
or not. Really, Yeah, the black hat hackers are malicious,
they're criminals. The white hat hackers are security experts helping
companies stop them.
Speaker 1 (07:52):
And there's a middle ground too, isn't there There.
Speaker 2 (07:54):
Is the gray hat hackers. They're somewhere in between. They
might find a flaw and exploit it without permission, but
then they'll notify the company afterward. But pen testing, that's
exclusively the domain of the ethical white hat.
Speaker 1 (08:06):
So what is that white hat penetration tester trying to achieve?
What's the end goal?
Speaker 2 (08:12):
The goal is definitive proof of risk. They use exploits
to gain a shell or root access, basically administrative level
control over a target system.
Speaker 1 (08:21):
And if you can get root access, if you can.
Speaker 2 (08:23):
Get root access, you can definitively tell the organization that
they are vulnerable to a real attack that could lead
to data theft or a total system compromise. The single
most crucial tool for this is the metasplit framework.
Speaker 1 (08:39):
Okay, so when an organization hires a team for this,
I'm guessing it matters how much information you give that
team to start with.
Speaker 2 (08:45):
Oh, it matters enormously, and it dictates the type of
test being run.
Speaker 1 (08:49):
I assume less information simulates a more challenging, more realistic scenario.
Speaker 2 (08:54):
Exactly in a black box test, the ethical hacker gets
no information at the start. It simulates an outside attacker
trying to breach the system coal and the opposite. The
opposite is white box test. The ethical hacker gets all
the information network diagrams IP addresses everything. This simulates an
attacker who's had time to study the system, maybe an insider.
(09:14):
And then you have the gray box test, which is
a blend of the two.
Speaker 1 (09:17):
And while this test is happening, you hear a lot
about these different teams inside the company sort of fighting
each other.
Speaker 2 (09:23):
Yes, and this is the institutionalization of that offensive mindset.
The consultant team trying to attack the system is known
as the red team, and the defenders their opponents. The
defensive team within the company trying to protect the network
and react to the intrusion, are the Blue team. This
competition is critical. It tests not just the technology, but
(09:44):
the people and their ability to respond to a live event.
Speaker 1 (09:47):
That makes sense.
Speaker 2 (09:48):
Now, one final crucial point about using outside consultants for this,
the legal and logistical side is paramount. Before any test begins,
you have to be extremely careful toify the scope.
Speaker 1 (10:01):
The scope of testing, so what systems are included and
what's off.
Speaker 2 (10:04):
Limits exactly, and the rules of engagement.
Speaker 1 (10:07):
Rules of engagement meaning things like are they allowed to
cause a network outage? Should they stop if a system
goes down?
Speaker 2 (10:13):
Precisely and if you are the penetration tester, you absolutely
need a strong legal contract or service level agreement with
the client that defines all of that. Without that prior agreement,
you could be in serious trouble. Running exploits could make
the tester criminally liable under the US's Computer Fraud and
Abuse Act the CFAA. It's the major piece of legislation
(10:36):
that without that contract could land you in serious legal
trouble just for doing your job. That legal protection is
non negotiable.
Speaker 1 (10:43):
So the outcome of all this offense and defense, this
Red team versus Blue team, it isn't just a bunch
of exploited systems. It's a formal record correct.
Speaker 2 (10:51):
The end product is a detailed report delivered to the
IT department. This report is the gold standard for security assurance.
It has to rank all the vulnerable found by importance,
is it critical, high, medium, or low risk.
Speaker 1 (11:04):
And tell them how to fix it and.
Speaker 2 (11:05):
Provide clear actionable recommendations on exactly how to patch those
security holes.
Speaker 1 (11:10):
So what does this all mean? We've kind of completed
this journey moving from identifying the big categories of attacks
to using professional tools like NMAP and nessus to assess
weaknesses and finally using ethical hacking with tools like metasploit
to prove where the holes really are.
Speaker 2 (11:25):
It's a cycle.
Speaker 1 (11:26):
This constant cycle of simulation Red team versus Blue Team
is how organizations move past that passive defense and achieve genuine,
continuous security assurance.
Speaker 2 (11:37):
To help solidify this concept for you, here's a short exercise.
If you are advising a company that wants to specifically
test how well their internal security teams catch zero day attacks,
vulnerabilities they don't know about yet, which type of penetration
test white box, black box, or gray box would you
recommend they run and why?
Speaker 1 (11:55):
And while you think about that, here's a final provocative
thought for you. The formal report at the end of
a penetration test is crucial, but true security isn't just
about patching the systems in that report. It's about institutionalizing
that Red team Blue team adversarial mindset throughout your culture.
And if your organization relies on proprietary, custom built software,
the assessment has to extend beyond just network devices and
(12:18):
standard applications to rigorously analyze that custom code is their
biggest vulnerability, the expensive firewall they just installed, or the
application they just finished building themselves,
You know, when you think about jobs in tech, network
security has to be one of the most uh just
incredibly stressful fields out there.
Speaker 2 (00:08):
Oh without attack, because.
Speaker 1 (00:09):
If you're the one defending a network, you have to
be right one hundred percent of the time. You're securing
this massive perimeter against every single possible angle.
Speaker 2 (00:19):
Of attack, every single one.
Speaker 1 (00:20):
But the malicious attacker they only need to find one
vulnerable window, one tiny crack in the armor, and they've succeeded.
Speaker 2 (00:30):
That's the fundamental asymmetry of it.
Speaker 1 (00:32):
It really is. Playing defense is just inherently harder than
playing offense in the digital world. Okay, let's unpack this.
If defense is so you know, inherently difficult, what is
the most successful security strategy you can adopt?
Speaker 2 (00:45):
Well, it's a bit ironic.
Speaker 1 (00:47):
Really, the answer is to stop playing defense altogether and
just switch sides exactly.
Speaker 2 (00:52):
The most effective security strategy is taking a proactive offensive approach, thinking.
Speaker 1 (00:56):
Exactly like an attacker would about your own network.
Speaker 2 (00:59):
You have to learn how to break your own system
before someone else does.
Speaker 1 (01:02):
So that's what this is all about.
Speaker 2 (01:04):
That is precisely the mission for this deem dive. You
you can't manage or secure what you haven't thoroughly tested.
We are going beyond the theory today. We're going to
discuss the three pillars of modern network defense. First, how
to understand the threat landscape, then how organizations find their
own weaknesses, and finally how they actually simulate live attacks
(01:25):
to stay secure.
Speaker 1 (01:26):
So let's start there with the offensive mindset the threat landscape.
We have to face a pretty hard truth that INFOSEC
experts lay out all the time. And what's that an
organization can spend I mean an unlimited amount of money
trying to secure their environment and still not guarantee you
one hundred percent prevention of an outside attack.
Speaker 2 (01:46):
It's impossible. So mitigation and just deeply understanding the enemy's
playbook become absolutely key.
Speaker 1 (01:52):
It's the foundation, right it is.
Speaker 2 (01:54):
If you don't know the playbook, you can't defend the goal.
So instead of listing every single attack method out there,
it's more useful for you to think about them in categories. Okay,
and we really see three major categories dominating in the
real world. First, you have social engineering.
Speaker 1 (02:08):
Attacks the human element exactly.
Speaker 2 (02:11):
These target human weakness. The biggest players here are phishing
and spear phishing, you know, tricking users into giving up
credentials and what else falls in that bucket, And the
more passive eavesdropping attack where an attacker is just listening
to network traffic or data as it's being transmitted.
Speaker 1 (02:28):
Social engineering just feels, i don't know, cheap and easy
for the attacker to deploy it is, which.
Speaker 2 (02:33):
Makes it incredibly common. So the next category is what
i'd call disruption and access attacks. Okay, these are all
about brute force or interception. This includes the denial of
service or DOSS attack.
Speaker 1 (02:46):
Where the goal is just to overwhelm the system so
it crashes YEP, and.
Speaker 2 (02:51):
The Man in the middle or MITM attack, which involves
intercepting and maybe even altering communication between two parties without
them knowing.
Speaker 1 (02:59):
So what about the technical attacks, the ones that go
after the code itself.
Speaker 2 (03:03):
That's the third category, application flaws and exploitation. These attacks
hit directly at weaknesses in software, especially custom web applications.
Speaker 1 (03:12):
The classic examples.
Speaker 2 (03:13):
The classics SQL injection, where malicious SQL queries are put
into input fields to corrupt or expose the database, and
cross size scripting or EXSS.
Speaker 1 (03:25):
Right, where unauthorized code gets run through a trusted website.
Speaker 2 (03:28):
Because the site didn't properly validate its inputs. If you
understand those three categories, you're already in a much much
better place to deploy countermeasures.
Speaker 1 (03:36):
Which brings us to the next crucial step. Knowing the
list of threats is step one. But how do you
actually prove your network is secured against them? You can't
just assume your firewall is working. You have to test
it regularly.
Speaker 2 (03:48):
And this is where we transition from understanding threats to
proactive self examination. This is the realm of the vulnerability assessment.
Speaker 1 (03:57):
So what is that exec At.
Speaker 2 (03:59):
Its core, assessment is a rigorous, in depth examination of
an organization's IT security policies, it's infrastructure, it's procedures. You're
evaluating everything against the risks the company.
Speaker 1 (04:10):
Faces, and the main purpose is just to find the
weak spots.
Speaker 2 (04:13):
It is to uncover information about known weaknesses in your
current security controls.
Speaker 1 (04:17):
So does this rely on one method or is it
more of a mix.
Speaker 2 (04:21):
It's a mix. It involves both automated tools running on
scripts and manual testing where an expert actually tries to
find the holes that a machine might have missed.
Speaker 1 (04:31):
So where you start.
Speaker 2 (04:32):
The first typical step is running a network discovery scan
just to define the scope to see what systems are
even on the network. A decades old but still wildly
popular tool for this is NMAP, the Network Mapper. It's
fantastic for finding out what devices exist and what ports
and protocols they're using.
Speaker 1 (04:51):
NMP. That sounds like a pretty hardcore command line tool,
right it can be.
Speaker 2 (04:55):
Yeah, it's incredibly powerful.
Speaker 1 (04:57):
So for someone just starting out trying to learn this,
is there an easier way in?
Speaker 2 (05:02):
Oh? Absolutely, that's the beauty of NMAP. It has a
user friendly graphical interface version called zenmap. Oh okay, and
it basically gives you training wheels while you're learning how
to properly craft and generate the NMAP commands. In the background,
it's a great way to visualize the network.
Speaker 1 (05:17):
Got it? So, once that initial scam is done, what's next?
Speaker 2 (05:21):
Then we move to advanced vulnerability scanning. These specialized scanners
go beyond just finding open ports. They actively check systems
and applications for known vulnerabilities, flaws.
Speaker 1 (05:34):
That have already been documented and you know, supposedly patched exactly.
Speaker 2 (05:37):
The two primary industry names to know here are nessis
and open VAS.
Speaker 1 (05:42):
And I imagine the assessment doesn't stop at the network level. Right,
especially for companies running their own custom software, the application
is often the easiest point of entry.
Speaker 2 (05:51):
That's spot on. For proprietary code, we need tools for
specific application analysis. If you're testing a web application, tools
like burpsuite are essential for checking common web flaws.
Speaker 1 (06:02):
And what about that SQL injection we mentioned.
Speaker 2 (06:04):
For that, you do something like sql map, which is
used specifically for automatically testing for those really dangerous SQL
injection vulnerabilities.
Speaker 1 (06:12):
Here's where it gets really interesting. If you're a cybersecurity
professional or say a student, looking to practice with these
tools ethically, you don't have to download twenty different programs
and install them one by one.
Speaker 2 (06:24):
No, that would be a nightmare, and that's a key
piece of practical advice. The vast majority of these professional
testing tools are all conveniently consolidated into specialized Linux.
Speaker 1 (06:35):
Distributions like Callie Linux.
Speaker 2 (06:37):
Cali Linux, or Parados. Those are the big two. My
advice is always to download one of those and run
inside a virtual machine a VM. Yeah, that way you
can practice with real world applications in a safe, sandboxed
environment without messing up your main operating system.
Speaker 1 (06:53):
Okay, so running a vulnerability assessment gives you a checklist,
a list of known weaknesses. But that checklist just tells
you there might be.
Speaker 2 (07:00):
A hole, right, It doesn't prove it.
Speaker 1 (07:03):
So how do you know if those weaknesses are actually exploitable.
That's what takes us to the third most advanced stage,
active testing.
Speaker 2 (07:11):
That is the definition of penetration testing or pen testing.
This is the next level after a simple assessment. We
aren't just finding vulnerabilities anywhere.
Speaker 1 (07:19):
It's actively trying to exploit them.
Speaker 2 (07:21):
We are actively trying to exploit them in a controlled
ethical environment to prove the whole exists and to demonstrate
the actual risk to the organization. This is often called
white hat hacking.
Speaker 1 (07:33):
When you say white hat, you're making a distinction between
the good guys and the bad guys.
Speaker 2 (07:37):
Precisely, we have to be clear about the moral spectrum here.
The term itself came from old Western movies. Believe it
or not. Really, Yeah, the black hat hackers are malicious,
they're criminals. The white hat hackers are security experts helping
companies stop them.
Speaker 1 (07:52):
And there's a middle ground too, isn't there There.
Speaker 2 (07:54):
Is the gray hat hackers. They're somewhere in between. They
might find a flaw and exploit it without permission, but
then they'll notify the company afterward. But pen testing, that's
exclusively the domain of the ethical white hat.
Speaker 1 (08:06):
So what is that white hat penetration tester trying to achieve?
What's the end goal?
Speaker 2 (08:12):
The goal is definitive proof of risk. They use exploits
to gain a shell or root access, basically administrative level
control over a target system.
Speaker 1 (08:21):
And if you can get root access, if you can.
Speaker 2 (08:23):
Get root access, you can definitively tell the organization that
they are vulnerable to a real attack that could lead
to data theft or a total system compromise. The single
most crucial tool for this is the metasplit framework.
Speaker 1 (08:39):
Okay, so when an organization hires a team for this,
I'm guessing it matters how much information you give that
team to start with.
Speaker 2 (08:45):
Oh, it matters enormously, and it dictates the type of
test being run.
Speaker 1 (08:49):
I assume less information simulates a more challenging, more realistic scenario.
Speaker 2 (08:54):
Exactly in a black box test, the ethical hacker gets
no information at the start. It simulates an outside attacker
trying to breach the system coal and the opposite. The
opposite is white box test. The ethical hacker gets all
the information network diagrams IP addresses everything. This simulates an
attacker who's had time to study the system, maybe an insider.
(09:14):
And then you have the gray box test, which is
a blend of the two.
Speaker 1 (09:17):
And while this test is happening, you hear a lot
about these different teams inside the company sort of fighting
each other.
Speaker 2 (09:23):
Yes, and this is the institutionalization of that offensive mindset.
The consultant team trying to attack the system is known
as the red team, and the defenders their opponents. The
defensive team within the company trying to protect the network
and react to the intrusion, are the Blue team. This
competition is critical. It tests not just the technology, but
(09:44):
the people and their ability to respond to a live event.
Speaker 1 (09:47):
That makes sense.
Speaker 2 (09:48):
Now, one final crucial point about using outside consultants for this,
the legal and logistical side is paramount. Before any test begins,
you have to be extremely careful toify the scope.
Speaker 1 (10:01):
The scope of testing, so what systems are included and
what's off.
Speaker 2 (10:04):
Limits exactly, and the rules of engagement.
Speaker 1 (10:07):
Rules of engagement meaning things like are they allowed to
cause a network outage? Should they stop if a system
goes down?
Speaker 2 (10:13):
Precisely and if you are the penetration tester, you absolutely
need a strong legal contract or service level agreement with
the client that defines all of that. Without that prior agreement,
you could be in serious trouble. Running exploits could make
the tester criminally liable under the US's Computer Fraud and
Abuse Act the CFAA. It's the major piece of legislation
(10:36):
that without that contract could land you in serious legal
trouble just for doing your job. That legal protection is
non negotiable.
Speaker 1 (10:43):
So the outcome of all this offense and defense, this
Red team versus Blue team, it isn't just a bunch
of exploited systems. It's a formal record correct.
Speaker 2 (10:51):
The end product is a detailed report delivered to the
IT department. This report is the gold standard for security assurance.
It has to rank all the vulnerable found by importance,
is it critical, high, medium, or low risk.
Speaker 1 (11:04):
And tell them how to fix it and.
Speaker 2 (11:05):
Provide clear actionable recommendations on exactly how to patch those
security holes.
Speaker 1 (11:10):
So what does this all mean? We've kind of completed
this journey moving from identifying the big categories of attacks
to using professional tools like NMAP and nessus to assess
weaknesses and finally using ethical hacking with tools like metasploit
to prove where the holes really are.
Speaker 2 (11:25):
It's a cycle.
Speaker 1 (11:26):
This constant cycle of simulation Red team versus Blue Team
is how organizations move past that passive defense and achieve genuine,
continuous security assurance.
Speaker 2 (11:37):
To help solidify this concept for you, here's a short exercise.
If you are advising a company that wants to specifically
test how well their internal security teams catch zero day attacks,
vulnerabilities they don't know about yet, which type of penetration
test white box, black box, or gray box would you
recommend they run and why?
Speaker 1 (11:55):
And while you think about that, here's a final provocative
thought for you. The formal report at the end of
a penetration test is crucial, but true security isn't just
about patching the systems in that report. It's about institutionalizing
that Red team Blue team adversarial mindset throughout your culture.
And if your organization relies on proprietary, custom built software,
the assessment has to extend beyond just network devices and
(12:18):
standard applications to rigorously analyze that custom code is their
biggest vulnerability, the expensive firewall they just installed, or the
application they just finished building themselves,
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