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 Hello everyone. Welcome back to the pen testing Essentials course.

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 In this video. We're going to be taking a look at how

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 to perform firewall detection and evasion with

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 nmap. Now, as I mentioned in the previous

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 section, we are going to be dealing primarily with

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 Windows systems. And one thing that all

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 Windows, operating systems were the way talking about Windows Server,

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 Windows 2000 and Windows 2008

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 to 2016. 2012 08,

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 talking about desktop additions or Windows 10.

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 27 Windows 8.1, all of them.

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 Have one thing in common. And that is they have Windows Firewall

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 in place right now. Windows Firewall can

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 can be again an issue depending on

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 the way it's configured. Now. The first thing we need to

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 do as any pen test is, we need to understand if

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 we actually have a firewall running and

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 if the firewall is active and the easiest

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 way we can do that within map is by running or

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 by performing an act probe scan. Now.

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 Sonic probe scan works, very different day. It

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 works very differently and counter-intuitively to

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 how the default TCP. 3-way handshake is

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 initiated. And, again, how it is completed, in

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 terms of the sequence, what we're doing now,

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 instead of sending your tea, your simple syn packet to

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 your target. We're now going to send a packet with only

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 the app probe or the ack flag set and

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 doing this will allow us to determine whether the

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 target is actually being filtered by

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 Firewall or that's being protected by a firewall or

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 whether it really is not being protected by a firewall or the

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 fire wall isn't active and we can easily run this

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 on any Target. And what I'm going to do now is I'll

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 open up the Metasploit bo3 virtual machine here. And

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 I will, I will just open up

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 Windows Firewall here. So it's a Windows Firewall and

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 we'll open up the wheel and we will say,

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 I want to turn Windows firewall on or off.

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 So I'll turn it off, just for a

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 Second. I just want to show you something, so

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 I will turn it off and I'll open up my Kali virtual

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 machine again, and we'll run the app probe scan. So

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 we say and map, and we can specify the port's that

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 we interested in. But in this case, I'll just leave it to the default. So

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 I can say in map and we say s a

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 so lowercase s uppercase a and the target

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 IP.

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 We hit enter. It's going to say we require root privileges. So

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 I'm just going to provide them.

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 And then we are just going to attend turn again. We'll just

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 let this can complete and you can see immediately tells

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 us that the host is obsolete, forms.

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 Host Discovery we get. We then can see that it

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 tells us all 1000 scanned ports on the

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 Target or unfiltered. So that means that it's the all

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 1000 Bots are not being protected or

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 not being filtered by a firewall. All

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 right now, that's because we've disabled the firewall, but just

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 to prove to you that this can does work. I will

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 Divide the firewall. So I'll open up manipulatable three

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 year again, and I'll go again. I'll say turn Windows

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 Firewall or on or off. I'll turn it on for both

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 public and private networks, and I'll just hit OK, here

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 and we'll go back into Kelly and I'll

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 run that one more time just to show you. So, I'll hit enter and

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 we can compare the results. You can see for

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 one. The, the actual scan is taking longer. So

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 that's an indication that something is changed. So

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 again, we'll just let the scan complete here. So there

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 we are.

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 ER, should take just a few more seconds. Again.

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 It's going to take significantly longer than the

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 actual, then a scan where you don't have

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 a firewall in place. But again, this is one of the

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 great things about nmap is the ability to detect. Whether,

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 you know, we have a firewall up or or not.

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 So you can see in this case. We now get the

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 same scan results. The host is up, but instead of telling us

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 that the ports are our unfiltered, we can now see

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 tells us that all 1000 scan ports on

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 the

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 Are filtered, which means there is a firewall in

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 place and this may hinder your scans. All

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 right. So now that we've taken a look at at

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 how to detect firewalls with nmap using the app, probe. We

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 can now take a look at some common firewall evasion techniques.

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 All right, so let's get started with that. So the

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 first thing we are going to be taking a look at is the

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 is one of the most common techniques that has been used

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 for quite a while. And that is the ability to actually fragment

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 your packets into smaller.

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 Aller 8, byte packets, right? So to

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 do this, all we need to do is we need to say if we are running

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 a simple scan here. We can say fragment and

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 we can use the - lowercase f, that means

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 fragment and this will fragment it into eight byte

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 packets. And of course, you can analyze this yourself. And

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 again, the the whole idea behind reducing the

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 size of the packages to fragment a packet. So that

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 when it's passing through or firewall, the firewall is not

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 able to detect what's actually being

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 Sent to the Target because it's all in free. It's

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 all in fragments as opposed to a single packet that

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 contains information that the firewall might flag as as

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 malicious, right? So if we say nmap F,

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 and we can then, you know, specify our own types of scans,

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 like nmap fsv specify a

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 fast scan here and then we can type in

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 the Target IP here. So I say hit enter again,

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 you can see, it's going to tell me the frogs, can requires root

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 privileges. So I'll just hit pseudo and I'll

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 just

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 Hit enter now one more time. So

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 again, we'll just let that run. Now. One of the issues that you'll

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 have with with fragmentation is fragmentation, was

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 really used on older older

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 firewall. So again, it can used or it can be used on

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 a few old Legacy Windows systems. It also

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 is very effective. I've tested this myself on Windows Server,

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 2008 system. So you can use this again for

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 for very basic level of evasion. So

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 again, we're just going to let this can run and

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 then

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 Going to take a look at performing a since can

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 or a stalled scan as it's known. And then we'll also take talk

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 about decoys and specifying your empty you

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 as an additional option as well. Alright,

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 so as you can see, we get our results back and

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 again, we get the exact same results we would have gotten. And

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 again, the fragmentation really didn't make much of

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 a difference apart from slowing down the scan. Because remember, we're fragmenting

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 the packets into smaller pieces, which means

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 the requests are.

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 Owing to be fragmented. And then they need to be sent to the Target where

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 they are reassembled, and then interpreted, and then a

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 response is sent back. So again, that is fragmentation in

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 a nutshell. It's a very basic technique that's used.

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 Now. Let's talk about one of the most important types of

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 scans and that is your sin or your stilts can, if

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 I just clear up my terminal year, so I'll say man and

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 I'll say man and map

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 Right, enter. You can see that.

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 I'll look for the since Cannon. We're looking for the first option

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 that is denoted by a minus S1,

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 lowercase, and uppercase s.

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 So, the since can is the default and most popular

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 scan option for good reasons. It can be performed quickly,

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 scanning, thousands of stealth is can scanning thousands

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 of device devices, as stealthily

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 as possible because it

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 Never completes TCP connections. All right. So

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 this is the de facto scan that you should be running primarily

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 because it scans very quickly because it

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 is essentially splitting the TCP 3-way handshake

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 in half. And secondly, it's going to be extremely sturdy

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 because a firewall is looking for, you

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 know, you're it's looking for the complete TCP

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 3-way handshake. And if you cut it in half,

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 then it's really not going to be able to detect what's going on.

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 Exactly, because I'll explain it to you, very basically.

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 What's happening is in send instead of

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 completing the TCP 3-way handshake, where you send your syn

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 packet and then you wait, you wait

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 for a response from the target, which could either be a cynic.

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 If the device is up and then you respond with

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 a knack. What we're doing here is we

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 are sending a sin and then we wait for a response and

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 then irregardless of the response. We simply send a

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 reset packet back to the device and we

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 essentially splitting it in half making the scan shorter and

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 still

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 Thea to run. This can all we need to do is type

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 in nmap SS. So again - a

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 lowercase and uppercase s and then we specify our ports again.

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 I'll just use the 100 most common ports and

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 we can then specify our Target or any other

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 options that we would like. So for example, I

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 can say, I want service version detection, and a bit of

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 operating system detection. So, 10.0.0.0 X.

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 And we can then hit enter. So, what I'm going to

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 do now is

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 Just going to demonstrate this to you with Wireshark. Right?

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 So why shock is a traffic analyzer and

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 inspector allows us to analyze packets being sent and

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 received from our Target and I'll just specify more

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 ethernet 0 interface here. So I'm just going to start

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 the scan and it's going to say, it requires root privileges. So

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 I'll provide that with root privileges here. So pseudo,

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 we're just going to enter. And if I open up why shock

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 and I start the capture, now, you can see, we

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 have all of these syn packets being sent to the Target. So,

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 again,

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 I'll just wait.

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 I'll just wait for the actual scan to complete.

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 Let's see if that's, that's actually running here. There. We are.

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 It's running. And I'll just try and zoom in here.

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 Let me just try and zoom into the actual traffic being captured. Are

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 we all? So, I can now spread this

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 out, and I'll just say, I want my info right

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 over here. So you can see, we are sending our syn

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 packets right over here since insane. We then

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 get a syn, ack back from the target. You can see, the IP

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 10.0.0.0 X is the

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 The source and the destination is OIP. We

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 get a syntax. So that means that these ports are going to be open. So,

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 poor both Port 21 and 22 open.

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 You can see that specified right over here. We

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 can also open this up. You can see the source port and the destination Port

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 also listed right over here. Alright, so

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 that is how we can actually that

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 is essentially how this can works by sending syn

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 packets, but I just wanted to demonstrate that to you,

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 so that you have an understanding. So I'll just close this year. I

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 don't want to

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 Save the packets and then we are the scan is complete and

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 because we used the stealth can

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 for one. You can actually tell how much faster that's can

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 was and we get all the results we were looking for.

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 So there we. Are we able to get our operating system detection service

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 version detection. So on and so forth. All

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 right, so that is how to use the since can or the stealth scan

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 as it's known. Let's talk about a few other techniques.

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 One of the techniques that I want to show to you, which is

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 really cool. Is the ability to use the decoy. Now

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 a

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 Decoy is exactly what it is,

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 exactly what it states it is it is essentially using

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 an IP address or a decoy IP address

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 to perform your scan. So for

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 example, if we are on a network that

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 we are not supposed to have access to and we have

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 a firewall running or an intrusion detection system,

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 that is running an actively monitoring the network.

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 If we try an initial initiate, a scan on

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 a Target that we know we do not have permission to do so.

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 That would be flagged as a malicious as malicious

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 activity, irregardless of how we

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 we actually try and make it as stealthy as possible. So

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 what we can do is we can actually use another IP

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 or another set of ips as decoys to

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 actually trick any intrusion detection system of

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 firewall into thinking that the scan is coming from another

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 IP address, which is absolutely brilliant. So,

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 to do this, we have multiple, we

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 have multiple ways. We can do this. We

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 can actually,

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 Ali again, specifying. It is very simple. So again, if

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 I wanted to say and map and we can run any type of scan that we

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 want, we can say nmap. We want to run a stealth scan and

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 we want to run it on all 100, most

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 commonly used ports. If I want to use a decoy, I

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 use the - uppercase D option. Now

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 when we talk about specifying, a decoy, we can

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 specify random decoys and to

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 do this, we can say RND. Sorry,

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 that is a capital or

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 These four random, we then use the colon and

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 we specify the amount of random IP addresses that

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 we want to use an nmap will generate them

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 automatically. This is great, and I'll show you why in a

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 second. So, if I say, I want to use only three, random IP addresses

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 or decoy, and we specify the target IP.

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 Here. I'll open up, why shop? Just to show

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 you that three other IPS are using apart. And

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 these are not going to be our IP address or our Kali

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 Linux IP. So again, I'll open up a new tab here.

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 And if I list out the

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 IP address of the Kali virtual machine, you can see the IPS

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 10.0.0.0 in. So just

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 keep that in mind as we run this scan. So again,

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 I'll just stop the capture and I'll hit enter. It's going

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 to tell me to requires root privileges. I'll provide it with those root

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 privileges and we'll just capture a bit

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 of traffic here. The scan is complete and will stop the capture. So

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 if we go to the top here,

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 And we take a look at the sin request being sent. You

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 can see that the source IP address is not our

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 IP address at all. It's going to be these three IP

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 addresses that are going to be used and you can see them

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 being repeated frequently. So for example, you can see the

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 sequence is repeated after every every

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 sin packet has been sent so it sends one with to

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 8.1 sixty six point two one seven. It

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 then moves on to one ninety. Six point, one 62 and

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 then 2008 point to 49 and then it repeats.

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 Repeats again. So 28.1 60 61 96.1

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 62, 28 .2 49 so

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 you can see that. That is really that really

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 is brilliant because we can mask our activity as

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 other IP addresses, which is great. So if

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 you're on a private Network that, again, you

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 want to be as clandestine as possible. You can also make it look

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 like the scan is coming from a, an

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 authorized system on the network. So for example, if you,

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 if there is an administrator on the network,

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 You can actually spoof their IP address

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 to make it look like the scan is coming from their IP

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 address, which is brilliant. So again, we can do the

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 same thing. We say and Matt and I'll say we want to run a stealth scan.

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 We're going to run it on all 100, most

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 common ports and we can then specify our decoy.

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 And then we specify the IP we want to

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 use as our decoy in this case. Let's make this can

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 look like it's coming from the actual access point or the Gateway

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 or the router IP address. So you can say

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 10

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 Point zero point zero point one. And then we specify

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 the actual IP address of the target 10.0.0.0 6,

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 I'll hit enter. And again, it's

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 going to ask me for root privileges. I keep forgetting to provide it

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 with root privileges. We will start a new capture here.

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 So continue without saving and I'm going to hit enter and

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 we let that go. We let that continue scanning and then we

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 are the scan is complete and you can see right over here. It keeps sending its

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 in packets with the source IP of 10.0.0.0 one.

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 And again,

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 And it's really is brilliant. That the fact that you can

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 actually mask your IP address or use a decoy. I

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 IP address to make it look like the scan is coming from

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 another device on the network or another

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 device that is on the Internet or that is not part of

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 the network. Really, really is brilliant. So these are

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 the tactics primarily that I wanted to show you

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 in regards to in regards to firewall detection

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 and evasion. So that's pretty much going to

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 be all that. I wanted to cover in this video and I'll be seeing

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 you.

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 You in the next video?
