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Penetration Testing Defined

This skill, led by Anthony Sequeira, provides a comprehensive overview of penetration testing within the field of cybersecurity. It covers fundamental concepts, methodologies such as white-box, black-box, and grey-box testing, and the importance of ethical hacking. The skill also delves into the modern threat landscape, including ransomware and zero-day attacks, and offers guidance on setting up effective penetration testing labs using both traditional and cloud-based environments.

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38m 6 Videos 6 Questions

Skill 2 of 2 in Penetration Testing

Overview

Join Anthony Sequeira as he teaches you the fundamental concepts of penetration testing and how it fits into the field of cybersecurity.

Gain an understanding of threat actors, attack methods, and penetration testing methods, such as white-box, black-box, and grey-box tests.

What is Penetration Testing?

This Nugget helps you understand what penetration testing is and why it's an important part of cybersecurity operations.

Knowledge Check

A computer researcher discovered a new vulnerability in Microsoft Windows and has shared it on their public blog. This is an example of which of the following?

  1. AUnethical hacking
  2. BEthical hacking
  3. CHacktivism
  4. DWhite hat hacking

Verify your team's readiness — Request a Demo to verify practice assessments, completion reporting, and CSV / SCORM exports on the Team plan.

Modern Threat Landscape

This Nugget gets you familiar with your attackers, their methods of attack, and provides you with examples of recent major exploits.

Knowledge Check

This style of attack was so common in 2017, it became known as "the year of _____."

  1. ARansomware
  2. BDenial of Service
  3. CTrojan Horse
  4. DPhishing

Verify your team's readiness — Request a Demo to verify practice assessments, completion reporting, and CSV / SCORM exports on the Team plan.

Penetration Testing Methodologies

This Nugget covers common approaches to penetration testing.

Knowledge Check

In which type of pen test does the tester start out with a significant amount of information about the organization and its infrastructure?

  1. AWhite box
  2. BGrey box
  3. CBlack box
  4. DGold box

Verify your team's readiness — Request a Demo to verify practice assessments, completion reporting, and CSV / SCORM exports on the Team plan.

Penetration Testing Lab Fundamentals

This Nugget walks you through some simple steps to consider when building your own pen test lab.

Knowledge Check

Your PenTest lab is most likely an open network environment. True or false?

Verify your team's readiness — Request a Demo to verify practice assessments, completion reporting, and CSV / SCORM exports on the Team plan.

Leveraging the Cloud for Labs

This Nugget details some exciting options for the creation of your pen test lab.

Knowledge Check

You may need to obtain pen test permissions from a public cloud vendor before you begin testing. True or false?

Verify your team's readiness — Request a Demo to verify practice assessments, completion reporting, and CSV / SCORM exports on the Team plan.

Where to Next?

This Nugget provides a summary of what was covered in this skill and discusses what's next.

Knowledge Check

The preparation for a PenTest engagement is often the most critical part. True or false?

Verify your team's readiness — Request a Demo to verify practice assessments, completion reporting, and CSV / SCORM exports on the Team plan.

Conclusion

I hope this has been informative for you and I would like to thank you for consuming.

View Transcript

What is Penetration Testing?

0:00You don't have to hang around with the security

0:02engineers in your organization long before you hear

0:05mention of penetration testing.

0:07Pen testing is so cool.

0:09And I know you're anxious to get started.

0:12But before we jump headlong into actual penetration testing,

0:16let's spend some time defining exactly what we're

0:19talking about here.

0:21And it is a really interesting discussion,

0:23because it all stems around hacking.

0:25Yeah, we are going to be hacking when we

0:28engage in penetration testing.

0:30And a hacker, as even the National Institute

0:33of Standards and Technology would define,

0:35this is an unauthorized individual

0:38that is trying to gain access to some system that

0:42has security mechanisms in place to keep

0:44that unauthorized individual out.

0:47So right off the bat, it's like wait a minute,

0:50we're going to be engaged in something that is not ethical?

0:55Well, that's really what's happened.

0:57Hacking has evolved so much that we really

1:00need to separate out the ethical hacking

1:04from the unethical hacking.

1:06Ethical hacking is going to be doing things

1:09like penetration testing.

1:11And this is where we are going to be

1:14authorized to carry out security testing against systems.

1:19And typically, we are looking for vulnerabilities that

1:23might exist in the security.

1:24We'll look at the defenses that are put in place to see

1:28if they're actually working.

1:30And this is something, the penetration testing,

1:33that we'll want to do both periodically as well

1:37as randomly because we know things are going to be changing

1:40constantly in networks today.

1:42And clearly, we're going to need to make sure

1:44that our penetration test results and reports are

1:47up to speed with all those changes.

1:50Now keep in mind that penetration testing could

1:54be done in an unethical manner.

1:57Of course it could.

1:58In fact, this might even not be all that intentional.

2:02For instance, let's say we're doing some penetration

2:04testing against Windows systems and we

2:07discover some unknown vulnerability

2:11that exists inside of Windows.

2:13Yikes.

2:14Not good.

2:15We then go ahead, let's say, and go to our blog site

2:19and document this previously unknown Windows vulnerability.

2:24Well, technically, sorry, we have just

2:27engaged in unethical hacking with our penetration testing,

2:31because Microsoft is going to be very, very upset with us

2:35that we are now alerting to individuals out there

2:38that might do harm that there is this vulnerability.

2:42And perhaps in our blog we explain

2:44exactly how to trigger that vulnerability

2:47within the system.

2:48As part of this skill where you'll really

2:51get to penetration testing well, we'll

2:53take a look at the threat landscape that we have today.

2:57It's pretty scary, because the threat actors as we call them,

3:02those that might do us harm, they're

3:04more varied and diverse than ever.

3:07And then we also will talk about the overall methodologies

3:11that will be used with penetration testing.

3:13And finally, we'll even give you advice

3:16on how easy it can be today for you

3:19to set up a safe and effective pen test lab

3:23that you can utilize in order to experiment

3:26with many of the technologies I'll be demonstrating for you.

3:30So penetration testing.

3:31Think about it.

3:32It's often about validation.

3:34Yeah.

3:34It's an ethical hacking process that we'll go through

3:37to validate the security mechanisms that

3:40are in place for maybe it's very sensitive data that we

3:44are trying to keep secure in our organization.

3:47Without the penetration testing, we're

3:49not going to know if we did a good job in securing

3:52that information.

3:54I hope this has been informative for you.

3:56And I'd like to thank you for viewing.

Modern Threat Landscape

0:00I really need you to brace yourself.

0:02Incoming is probably one of the worst Bob Dylan impressions

0:06you've ever heard.

0:07Oh the times, they are a changing.

0:12Why does this song come to mind?

0:14Well, we're going to talk about the modern threat landscape

0:16when it comes to penetration testing

0:18and, Yeah, a lot has changed and always will change.

0:23Think about the year 2017, for example.

0:26This became known as the year of ransomware.

0:30That's how prevalent ransomware attacks have become.

0:34And think about it.

0:35If we go back 10 years from this point,

0:37no one had even thought of the word ransomware.

0:40So it's interesting how things like this happen too.

0:44We can learn so much from some of

0:47the famous ransomware attacks.

0:49The example that I'm showing you right here

0:51is the very famous WannaCry example.

0:55How did the WannaCry ransomware attack

0:58end up affecting an estimated 350,000 IP

1:04addresses across the globe?

1:06Well, it was taking advantage of a Server Message Block SMB

1:12vulnerability found in Windows.

1:15The vulnerability was named EternalBlue.

1:19And this vulnerability in SMB Microsoft knew about.

1:23They had released a patch for this vulnerability.

1:26But no one took it really seriously.

1:29And the EternalBlue vulnerability

1:31ended up giving the door into the WannaCry ransomware

1:36attack that caused all these many problems.

1:39So this is just a representation of a couple of things--

1:43how this landscape changes and we end up getting attacks

1:47that are of a new category even.

1:50And it also represents how this vulnerability

1:54leads to this attack which leads to this attack.

1:58So everything's connected, man.

2:00And this is something that we'll see again, and again,

2:03and again as we work throughout these pen test skills.

2:07Something else that's super interesting

2:09that we'll be tackling is zero day type of attacks.

2:13So when there is some brand new attack

2:16that we have never seen before, it's called a zero day attack.

2:20And of course, one of the very interesting things about that

2:23is how in the world would we ever protect ourselves

2:27against it?

2:28I mean, there are no IPS signatures for it.

2:32There are no definitions for it in antivirus databases.

2:35So zero day is a very interesting topic

2:38that we'll be exploring.

2:40And then yet another super interesting topic

2:43is the Internet of Things, or IoT.

2:46Attacks are happening in this category.

2:48And one of the most fascinating comments

2:50on this that I ever heard was at a large tech conference

2:54where this IoT big shot got on the stage--

2:57and I didn't mean that negatively.

2:59He was really a big shot.

3:01This guy got on the stage and he said, you know,

3:03what's scary about the IoT security landscape?

3:07We don't know what's scary.

3:10We don't even know the kind of damage that could be done.

3:13We don't even know what the threats are going to look like.

3:16And that was the scariest part for him.

3:20And another thing that's really evolved and will continue

3:22to evolve are what we call the threat actors, those

3:25that seek to do these kinds of hacking activities against us.

3:31That's changing all the time.

3:33I mean, we've got organized crime in the game now,

3:36you know like Tony Soprano in the group.

3:38Hey, forget about it.

3:41We've got hacktivists.

3:42Yes.

3:43One of the famous groups called Anonymous.

3:46this right here is their flag.

3:48This right here is their little calling card

3:50that you will see after you've been attacked.

3:53This right here is those really, really freaky masks

3:56that they will wear.

3:57And you know, all of this stuff is centered around,

4:00oh, we're hacking, sure, and we're

4:02committing computer crime.

4:03Sure we are.

4:05But we're not doing it for financial gain.

4:07We're doing it for political reasons perhaps

4:10or social awareness reasons and all that kind of stuff.

4:14The main thing that I want you to remember

4:16is it's not money as the motivator with the hacktivists

4:20most typically.

4:21There's state-sponsored attacks where

4:23we have one country saying, hey, let's disable the systems

4:28of another country.

4:29Scary.

4:30And then, of course, we've always had this category.

4:34And this is by far the biggest category.

4:36And that is when we have attacks that

4:39are coming from disgruntled or even nondisgruntled users

4:43inside of our organization.

4:45Just like everything else, we have

4:47to consider that there are malicious versions of this

4:51and nonmalicious versions of this.

4:53But insider attacks, oh my goodness.

4:56They're so common.

4:57And we don't really even know how common

4:59they are, because not all of them are being reported.

5:02Many times these attacks come and the organization

5:06is under no legislative requirement

5:09to report the activity so they don't report

5:12the activity, leading me to make that statement of boy

5:15are they common.

5:16And we don't even know how common they are.

5:19Now as you and I are operating as part of the forces of good,

5:24you and I need to realize that, look, this is not all bad news.

5:27I mean, this Nugget may be like the ultimate buzzkill, right?

5:31No, no, no.

5:32It's not all bad news.

5:33We are going to have tools at our disposal

5:36as you'll see that are very, very sophisticated compared

5:39to what they used to be.

5:40And we're going to be able to do things that we were never

5:42able to do before when we are engaging in penetration

5:46testing.

5:47And then, of course, as is so typical,

5:50we are really helping organizations

5:53to guard against this ever evolving threat landscape.

5:58I hope this Nugget was informative for you.

6:00And I'd like to thank you for viewing.

Penetration Testing Methodologies

0:00[TECHNO MUSIC]

0:10Think about it.

0:11A computer criminal, they're going

0:13to have a methodology as they're attacking us.

0:16It only stands to reason that, as penetration testers,

0:19we should have a really rock solid methodology as we

0:22are testing for the security in our systems.

0:26And I think this becomes even more

0:27obvious in today's landscape.

0:29And that's because one of the things that we see consistently

0:32is systems just keep getting more and more complex.

0:36So as the system grows in complexity

0:39that we are pen testing, the methodology that we use better

0:43be rock solid.

0:44And another reason we really want

0:46to come up with solid methodologies

0:49is because of what we call scope creep.

0:51This happens a lot.

0:53So it is our goal to pen test some component

0:56and then, inevitably, the pen testing

0:59starts spreading out to additional components.

1:03And now we're running into problems

1:04that we did not anticipate.

1:06We are producing reports that contain information

1:10that the person that we're pen testing for

1:13might not have even wanted to see.

1:15So we got to make sure that we really define scope.

1:19And I'll have a skill for you covering that, of course.

1:22And that will be one you do not want to skip.

1:24Now something else too that is really

1:27going to help us if we have a methodology that's

1:30tried and true that we are utilizing

1:32is the fact that, with the documentation that we

1:35are inevitably going to be needing to provide the client,

1:39the documentation is really facilitated

1:43through a careful, well thought through methodology.

1:46So we are almost, in a sense, automagically creating

1:50a lot of that documentation just through the great methodology

1:54that we're using.

1:55And speaking of the complexity of modern systems,

1:58we really need to group methodologies under the web

2:03application tests that we might be running, the network

2:06infrastructure tests, wireless, physical facilities,

2:10and social engineering.

2:12You may break this down into further categories.

2:15And keep in mind the delineations aren't always set

2:19in stone and rock solid.

2:20Let me give you a perfect example.

2:22We know that many web applications today

2:26are going to be built upon database technology.

2:29So there'll be underlying databases

2:31that store the information.

2:33The web application, one of its functions

2:36is to be a front end for that database

2:39and make the database information accessible.

2:43So as part of our web application testing,

2:47we will be doing things involving the database.

2:50But note it's really going to be constrained

2:54in scope to the web application aspects of the database.

2:58There may be other methodologies that we

3:01use against the underlying database itself

3:04for further testing.

3:05With network infrastructure tests,

3:07the sky's the limit, right?

3:08I mean, we may be dealing with our routers.

3:11We may be dealing with our firewalls.

3:13We may be dealing with switches.

3:17There is a wide variety and an ever-growing list

3:20of potential devices inside the infrastructure, which

3:24may need to be incorporated into our tests.

3:27I can't say enough about social engineering.

3:30So many of the massive attacks that we

3:32read about in the headlines today

3:35began with very relatively simple social engineering

3:40attacks that were successful.

3:42So this is an area that we really

3:44need to do due diligence on and provide

3:46a lot of great education on this topic to both the stakeholders

3:50as well as the employees or the clients of those stakeholders.

3:55Now before you get like super stressed out about all this,

3:59just realize that, like in so many areas of technology today,

4:02we don't have to operate from a vacuum.

4:05No.

4:06There's great classic methodologies out there

4:09that are documented for us.

4:10We'll be referencing them again, and again,

4:13and again in these penetration test

4:15skills like the penetration testing execution standard or p

4:20test.

4:21And no, that's not pee test.

4:23A p test is something different entirely.

4:25This is p tests.

4:27And we'll see where there's going

4:29to be excellent information inside of that standard.

4:32And it's going to give us Ike phase

4:35information in how we can operate

4:37in a tried and true manner.

4:39There'll be specific methodologies

4:41like the payment card industry data security standard.

4:45I'm pretty sure that's what DSS stands for.

4:48I know D is Data and S is Security.

4:51Data Security-- yeah.

4:52I got it right.

4:53Data Security Standard.

4:53Never question yourself, Anthony.

4:55And this is going to be a pen test guidance

4:58section of their documents that's

5:00going to be very, very valuable for us,

5:02things like the penetration testing framework

5:05and the open source security testing methodology manual

5:10is something that we will be taking

5:11a look at for its specific guidance in this area as well.

5:16Now the final point I want to make about methodologies as we

5:19really kind of zero in on defining what pen testing is

5:23all about is our box tests.

5:25You see there is testing that we do that couldn't be considered

5:30oftentimes or categorized as white box, black box,

5:33or you'll see gray box tests.

5:36What this is all about is simply how much information

5:39we have about the device or architecture

5:44that we are testing.

5:46If we know pretty much all there is to know about that entity,

5:50this is a white box test.

5:52So let's think about this in terms of like server operating

5:55systems.

5:56If the penetration test device that I

6:00am working with, if I know the exact version of the operating

6:06system, the patch level, the apps

6:09maybe that are installed inside of it,

6:11if I know all these great details,

6:13that's a white box test.

6:15But there are environments where we

6:17would want to be doing specifically black box tests.

6:21And that's where we know nothing.

6:23We're not provided any advanced information about the entity

6:27that we're testing.

6:28As you might guess, a gray box test

6:31would fall somewhere in the middle of these two approaches

6:34where we get limited information but at least some

6:38about that entity that we are testing.

6:41If you're confused on, OK, now wait a minute,

6:43when am I going to use which or the other, that is something

6:46we'll be working with throughout these skills as well.

6:49Now if you're like me, you're super

6:51anxious to get your hands dirty here

6:53to really jump in and start doing some penetration testing.

6:56And I've got great news for you.

6:58Next up in this skill, I'm going to have some nuggets for you

7:01that discuss the lab environment for penetration testing.

7:06And this is super exciting, because if we approach the lab

7:11environment properly, we can be up and running safely

7:16penetration testing in no time.

7:19I hope this Nugget was informative for you.

7:21And I'd like to thank you for viewing.

Penetration Testing Lab Fundamentals

0:00[MUSIC PLAYING]

0:15I hope you dug that little intro tune.

0:17It only took me 3 and 1/2 hours in GarageBand last night.

0:22So this Nugget is important for two big reasons.

0:25Number one, we want to learn to build

0:28a really awesome penetration testing lab

0:31so that we can learn these technologies.

0:34But perhaps even more important than that,

0:37we need to discuss pen testing labs

0:40that we may be creating when we're out there consulting

0:44or working for our employer and we

0:46need to do penetration testing against a lab environment.

0:50So really this is a two for one kind of Nugget.

0:53And in both cases, regardless of whether we are setting up

0:56our penetration lab for our own education as we're learning

1:00this skill or if we are setting up a penetration

1:03lab due to an engagement we are on with a client--

1:07you can say it, Anthony--

1:09then either of those situations, it's

1:12typically a little more complex than we're

1:14used to setting up this lab.

1:16And that's because, as we've alluded

1:18to earlier in this skill, things are more complex than ever

1:22today.

1:23There's going to be a wider variety of systems and devices

1:26than ever that we might need to be pen testing against.

1:29And great news.

1:31We have more tools than ever.

1:33But you certainly need to know the ins and outs of these tools

1:36to use them appropriately and successfully.

1:40Now keep in mind that many times when

1:43we are working with clients and we're pen testing, by design

1:48we are going to be testing against their production

1:51network.

1:52Yeah.

1:52And you know, that's the whole thing.

1:55They're like, OK, we have this system in place.

1:57See if you can penetrate it.

2:00And we're going to be very, very careful in scoping that.

2:03And we're going to be very, very careful

2:05that we don't like disrupt for measurable time

2:09periods their operation and all that kind of stuff.

2:11We'll give you guidance on this.

2:13But just keep that in mind that we are not always

2:16testing for them against what we often

2:19call a sandbox where we isolate the system

2:23and test in that safe kind of-- oh,

2:26what's it-- sanitary environment where

2:28we can't mess with production.

2:30So there are definitely two ways to approach that.

2:33We'll be getting into much more detail about it.

2:35We can't forget though, yes, as I alluded to,

2:38the practice lab is something that we're also

2:41going to be setting up.

2:42And that's a great opportunity for us

2:44to practice with our tools and to practice

2:47pen testing different systems and different devices.

2:52Now because this is complex enough of a lab

2:55that we are going to be working with,

2:56I wanted to give you some often fundamental concepts

3:02that we want to know when it comes to pen testing labs.

3:06Oftentimes, our pen test lab will need to incorporate access

3:10to a public network.

3:12Yeah, like the internet.

3:14So we have this pen test lab.

3:16And we're doing all this great pen testing inside it.

3:18But we do have need for worldwide web access

3:22for all kinds of reasons.

3:25And this is important to think about because this technically

3:30is therefore an open system.

3:33And we need to make sure that we have the correct protection

3:37mechanisms in place since technically it's

3:39open that we don't allow maybe even attacks themselves

3:44to flow outside of the network.

3:48We have an opposite approach.

3:50And that is to build a closed system.

3:53So we say nope, nope, nope, nope.

3:56There is going to be no ability whatsoever for this system

4:01to reach out to other networks, other devices.

4:04We're staying completely closed.

4:06And this is often the approach we

4:08have to take when we are in the confines of our organization.

4:12That's a headquarters building in case you didn't know.

4:14It's also a domino.

4:16So we need to make sure when we're in HQ

4:20and we're doing this, can you imagine

4:22how upset the IT department would be when we bring down

4:25key systems and we're like, hey, whoa, whoa,

4:27whoa, wasn't my fault. I was just doing my pen test practice

4:30like Anthony told me to.

4:32In fact, please do not say that ever.

4:35So yeah, open and closed systems certainly a consideration here.

4:40We may have private services.

4:42And that's a star.

4:43We may have private services that we

4:45are going to incorporate into the pen test lab.

4:49And you know, this might be like DNS, and DHCP, and NTP.

4:55And oftentimes due to scope, we don't

4:58want to impact these things.

5:00So really keep that in mind.

5:03Something else that I want to share with you

5:05is the concept of a clean or dirty network.

5:09So what we will do is we will have this clean network where

5:13we are operating and where those services that we need live.

5:18And then we come up with a partitioning scheme.

5:21And you guessed it, what exists below this partition

5:25is the dirty network.

5:27This contains the systems and devices

5:30that we're going to be attacking,

5:32that we're going to be testing.

5:33So that's another very common design

5:36when it comes to awesome pen test labs.

5:39They consist of the clean and the dirty network.

5:44So you'll notice that as we discuss other really, really

5:48fundamental concepts here when it comes to our lab,

5:51you'll note I begin with just a reminder

5:54that we often will use closed systems and closed networks.

6:00And the example I gave, I can't emphasize enough this

6:04is something we often have to do when

6:06we are in an environment like the production headquarters

6:10network where we work and we want

6:12to ensure there is no impact to the surrounding devices.

6:16More so than ever today, virtualization

6:19helps us out when we are pen testing.

6:21We can build a virtualized environment

6:25that contains many virtual networks

6:29and many virtual devices that are going to be easy for us

6:32to pen test against.

6:34And guess what?

6:35In the very next Nugget of this skill,

6:38I'm going to share with you a cloud solution that

6:41would clearly involve virtualized devices

6:45but would give us many, many conveniences

6:47that the cloud brings.

6:49This is being done more often than ever.

6:52When you're designing your lab, you

6:53want to be as realistic as possible.

6:56This isn't a problem if we are testing a production

7:00device for a client.

7:02I'll say it's realistic.

7:03It's the production device.

7:05But it gets more problematic when

7:07we are building a closed system, a sandbox system,

7:11and we are trying to replicate some environment for testing.

7:15We need to really spend a lot of time

7:17on this to make sure it is truly realistic for the production

7:21network that we are modeling.

7:23Modeling.

7:24I can say it.

7:25Monitored.

7:27We need more sophisticated and in-depth monitoring than ever.

7:32One of the reasons that we would do this

7:34is to, in the pen testing, see the impact

7:38that the hacker tools are having on the network.

7:41But also we need to make sure that all of this stays up

7:46and functional.

7:47We may accidentally overload RAM or CPU just

7:52with the usage of the tools themselves.

7:54And that's not realistic for this scenario.

7:57So what we tend to do is overprovision

8:00a lot in these labs so that we don't

8:03run into artificial problems artificial resource

8:07constraints, because, clearly, we

8:11want to be in scope for what we're testing.

8:15We might involve multiple OSs.

8:18And that's another thing that you'll

8:19see that the cloud is so wonderful for.

8:22And we'll probably want to take our tool set

8:26and test with one tool, and then test with another tool that's

8:30like that tool, and then test with a third tool that's

8:33like that tool, and using different tools that

8:36attempt to do the same thing makes for a much more robust

8:40penetration test.

8:42Finally, when it comes to practice targets,

8:44we need to be creative.

8:46If we're operating outside of a production network

8:50to maintain that level of realism,

8:53we need to make sure that we model

8:55as closely as possible the targets in our penetration

8:59testing.

9:00So if building realistic, and well-provisioned,

9:04and rock solid labs is something that excites you as it does me,

9:09you're going to love penetration testing because

9:12so oftentimes we are not operating

9:15for various reasons against production systems or networks.

9:19And we want to really construct a kick butt lab.

9:23That's the official terminology.

9:26In our next Nugget of this skill,

9:28I want to elaborate with you on that cloud concept,

9:32because there's some key advantages to doing that that I

9:34want you to be aware of and also some super important key

9:38caveats.

9:40I hope this Nugget was informative for you.

9:42And I'd like to thank you for viewing.

Leveraging the Cloud for Labs

0:00How in the world are we going to pull this off?

0:02The cloud.

0:03How in the world are we going to pull this off?

0:06The cloud.

0:07How in the world are we going to pull this off?

0:09The cloud.

0:11It might be that you're suffering from a little cloud

0:13fatigue, because we hear it as the answer

0:16so much for how we're going to solve a particular IT

0:20challenge.

0:21Listen, it's pretty legitimate.

0:23In this Nugget, let me show you of those characteristics

0:27that we talked about that often make

0:29for a great, successful pen test lab,

0:32of those characteristics, many can be directly addressed

0:36by moving to CloudTech.

0:39First of all, I really need to remind you, as we pointed out,

0:43remember, we may be doing penetration testing

0:47against a production network.

0:49And sure enough, with the popularity of cloud

0:52today, that production network your client

0:55may be running in the happy, happy cloud.

0:58It might be a public cloud.

1:00It might be a private cloud.

1:02It could even be a cloud that's part of a community cloud.

1:06So there's so many times where we'll

1:09be pen testing against somebody's cloud

1:12infrastructure.

1:13And it's so common, because so many clients today

1:17have moved to the cloud.

1:18And they're really kind of unsure

1:21about the security posture and security environment

1:24that they are operating within.

1:26But even if we are talking about a true lab,

1:30maybe for our learning practices or to sandbox

1:33and replicate a production environment that we're

1:36going to pen test against, the cloud

1:38is more and more appealing than ever today.

1:42But don't worry.

1:43If you're interested in setting up the classic data center

1:48architecture for your pen testing and maybe

1:51you're using all physical equipment in the data center,

1:53or if you're doing a data center and you

1:56are using virtualization inside that data center

1:59but you're not going all the way to cloud characteristics,

2:03no problem.

2:04In our pen test skills, we're going

2:06to be giving you examples of how to set all of this up

2:09and how to pen test against it.

2:11So if Cloud isn't your thing, I won't

2:15be biased as we move throughout these skills to the cloud.

2:18Now, do you remember this presentation

2:20from our previous Nugget in this skill?

2:23Sure.

2:24Think about how the cloud can actually

2:27help us accommodate so many of these common pen test

2:31lab mainstays.

2:33And some of them might even surprise you.

2:35For example, you might think, well,

2:37we can't do a closed environment in public cloud.

2:41No, no, no, no.

2:42Of course you can.

2:43You're going to have in the case of the famous Amazon Web

2:46Service example, you're going to have what is

2:49called a virtual private cloud.

2:52And you could have many of these, by the way.

2:54But in a single VPC, you could go ahead

2:57and you could do a totally private subnet.

3:01That's right.

3:01You can only get in there through something

3:04like Secure Shell, and it could be only you.

3:08And it will have no communication

3:10with any other entity.

3:12So yeah, we can do closed systems.

3:14In fact, we have even more flexibility

3:16with the cloud in setting them up.

3:17The cloud is powered by virtualization,

3:20so we can take advantage of that.

3:22We can get very realistic as far as modeling

3:26an actual infrastructure in the cloud,

3:28because we're going to have all kinds of opportunities

3:31for appliances that we might not be able to afford for a lab

3:36if we were having to go out and actually get

3:39the physical equipment.

3:40It is hyper monitored.

3:43You heard me right.

3:44Cloud implementations give us monitoring capabilities

3:47like never before.

3:48As far as provisioning resources go,

3:51the cloud gives us not only scalability, the ability

3:56to increase resources quickly and easily,

4:00but the cloud gives us elasticity.

4:03And elasticity would allow us to grow or shrink resources

4:07as we need them.

4:08We're going to have a ton of options for practice targets

4:11thanks to the marketplace that is available with cloud

4:14infrastructures today.

4:16They're going to accommodate all kinds of different OSs.

4:19And they'll even offer us tools built right in.

4:23Even if up to this point you've only

4:25had a casual interest in pen testing,

4:28you probably heard about one of the shining

4:31examples of tools that we have in our tool belt these days.

4:34It's called Kali Linux.

4:36Check this out.

4:37We're going to go up to the AWS Marketplace.

4:40And I'm going to go in here, and I'm going to do a search

4:42for K-A-L-I, K-A-L-I, K-A-L-I. It's Kali Linux.

4:50Woo-hoo.

4:51There it is.

4:52This is Free Tier eligible.

4:55That means we can get this highly updated

4:58version of Kali Linux, and it's going

5:01to cost us $0.046 per hour.

5:06And it's Free Tier eligible, meaning

5:09that we can spin this up at that total price with no charges

5:15whatsoever from Amazon Web Services.

5:18And this Kali Linux is only going

5:20to cost us $0.046 per hour.

5:23And that's when it's running.

5:25So if we're only using it for a couple of hours

5:27and then we don't even need it anymore,

5:29we have gotten our money's worth, to say the least.

5:34Now, I don't know if you remember this,

5:35but at the end of the previous Nugget,

5:38I was talking to you about how there

5:40are going to be caveats here.

5:42Two that come to mind immediately

5:44is the simple fact that we can't do everything with the cloud.

5:48I mean, think about physical security penetration testing.

5:54We don't have any physical.

5:56Oops.

5:57So yeah, we're not going to be able to pen test

6:00the physical infrastructure in a public cloud environment,

6:03because I'm pretty sure Amazon Web Services would be super

6:06upset if we showed up at one of their high tech data centers

6:10and we're like, we're here to pen test the physical security.

6:14Not going to go over all that well.

6:17The other thing that I wanted to mention right away

6:19here is, if you have a big client that you're working with

6:24and they're in, let's say, Amazon Web Services

6:27and they hire you to pen test against their production Amazon

6:32Web Service infrastructure, you are almost always

6:36going to want to obtain--

6:37you may even have to obtain--

6:40written permission from Amazon Web Services to do that.

6:43It makes sense, right?

6:44Amazon must know that the attacks that are coming

6:49are from you, and they need to know why you're doing

6:51it and all that great stuff.

6:53They have very much over the years

6:56loosened up on you taking a private subnet

6:59inside a virtual private cloud and doing your own little pen

7:02testing of systems inside that sandbox.

7:05They're not nearly as concerned about that,

7:07and it's evident why.

7:09But boy oh boy, be careful with any public cloud vendor

7:14if your plan is to pen test against production networks

7:20that they're hosting.

7:21Makes good sense.

7:22I hope this Nugget was informative for you,

7:24and I'd like to thank you for viewing.

Where to Next?

0:00I know.

0:01I know.

0:01You're probably not excited about penetration

0:03testing as I am.

0:05But I hope now that we've walked through these Nuggets

0:07where we really took a detailed look at exactly

0:11what penetration testing is all about,

0:13I sure hope you're almost as excited as me.

0:16And you're probably wondering, OK,

0:18I got a good handle now on penetration testing,

0:21and common methodologies, and things to watch out for,

0:24and different ways we can go about it.

0:27But what do we do next?

0:28Well, I would highly suggest that next you

0:31take a look at the skill where we

0:33are going to be really planning intensely

0:38for a successful penetration test engagement.

0:42I'm going to give you great strategies for planning,

0:44great tools that are going to help you plan.

0:46This is super important, because if we don't plan ahead,

0:50we could easily violate laws.

0:53We could get clients really, really angry with us.

0:57We could even--

0:58I shudder to think--

1:00give bad, bad advice when it comes to the security

1:04posture of an organization.

1:06I don't know about you, but I don't want that on my resume.

1:10I hope this Nugget was informative for you,

1:12and I'd like to thank you for viewing.

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