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Beginning Pen-200

The skill focuses on advanced penetration testing techniques, emphasizing the importance of thorough note-taking and timestamping to ensure accurate reporting and accountability. It covers the five phases of pen testing: reconnaissance, scanning, vulnerability assessment, exploitation, and reporting. The skill also highlights the significance of understanding risk management and the necessity of compiling an executive summary for stakeholders, summarizing key findings and recommendations for improving security measures.

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50m

Skill 1 of 46 in OSCP

Beginning Pen-200

It’s time for some advanced pen testing! We’ll see and learn about a wide variety of tools and techniques for testing systems and networks in the name of enhanced security.

And one of the building blocks to ensure better security is reinforcing what we’ve learned up to this point. In previous courses leading up to this, one of the key components we learned about was logging and note taking.

One important thing to remember when we conduct pen testing is that not all vulnerabilities will be patched after they are identified. This could be due to the organization accepting the risk based on their risk matrix.

Risk Management

We mentioned that some vulnerabilities may or may not be patched when we run our vulnerability assessment. It could be that when we conduct a pen test, the targeted organization is aware of some of the vulnerabilities we found and potentially exploited. So why weren't those vulnerabilities dealt with before our pen test?

Sometimes, it could be an accepted risk on part of the targeted organization. Based on the value of the system and its ability (or inability) to be patched or better secured, the targeted system was identified as having an accepted risk.

It's not for us to decide if an accepted risk is good for business or not because we're not the system/network owner. But it is good to know that this can come up in the course of you conducting a pent test.

Might I recommend a Program Management course here on CBT Nuggets that dives deeper into the risk assessment and management of programs as a whole.

Knowledge Check

Why is it important to take meticulous notes during a pen test?

Timestamps

Timestamps are crucial in penetration testing as they provide a clear timeline of actions taken, which supports accountability, reproducibility, and incident correlation. Including precise timestamps in notes ensures accurate reporting and strengthens the integrity of the executive summary by demonstrating a structured and professional assessment process.

There are ways to ensure you'll always have a timestamps when you run your commands. And I want to show you something you can run inside of your Kali terminal to ensure you're getting the most accurate timestamps from the system when you're running your tools.

Knowledge Check

Why are timestamps crucial in penetration testing?

Applying timestamps

It's one thing to just talk about adding timestamps, but you and I like to be complete in our note taking and have it at the ready when we're conducting our pen testing. Utilizing timestamps on each line of output in our terminal allows us to add an additional layer of verification and make it easier on us when we're taking notes.

#install moreutils
sudo apt install moreutils

#Get a timestamp with each line of output with your terminal commands
ifconfig -a | ts

Personally, I've been in situation where I've forgotten to record timestamps and I've had to go back and look them up. Utilizing | ts allows us to avoid doing that and keep our focus on the pen test itself.

#Adding timestamps to your bash history
bash
export HISTTIMEFORMAT="%F %T "

#running a bash history (should have time stamps)
history

Knowledge Check

Utilizing timestamps in terminal outputs can help verify actions during a pen test.

Note taking

A large part of pen testing is utilizing tools to test and validate security measures put into place on systems and networks. And there are a lot of tools out there that can help us achieve results.

But because there are so many different tools out there, it's important we remember to keep notes. I won't tell you how to keep notes. Mostly because this can vary based on personal preferences, business practices, law enforcement policies, or other factors.

I know you're still up on knowing the five phases of pen testing. But just in case a refresher is needed, I have them below for you so can you can get an idea of how note taking helps us in each of the areas.

  • Reconnaissance: Gathering preliminary information about a target system or network using passive and active techniques.
  • Scanning: Actively probing the target to identify open ports, services, and systems to better understand the attack surface.
  • Vulnerability Assessment: Analyzing discovered systems and services for known weaknesses that could be exploited.
  • Exploitation: Attempting to take advantage of identified vulnerabilities to gain unauthorized access or escalate privileges.
  • Reporting: Documenting findings, risks, and recommend remediations in a clear, structured format for stakeholders.

The key thing to remember here is that there are some basic bits of information we need to take note off when we conduct pen-testing.

  • Device tested
  • Hardware/Software utilized
  • Commands used
  • Timestamps
  • Witnesses?
  • Results

Knowledge Check

Match each phase of pen testing with its description.

This interactive assessment is available in the full learning experience.

Want to answer questions like this yourself?
with no purchase required. Already have an account?

Note taking in use

Let's work together on utilizing a pen testing tool and take some notes. As we walk through this together, we'll be able to see if we can look back on our notes and verify it's complete and understandable.

Below is the macro I use inside of Word to have timestamping available whenever I'm doing a report.

Be it on a Word document, pen and paper, or hammer and chisel, notes need to be as precise as possible and match as closely as you can to what is actually happening during the course of your pen test. And as important as that note taking is, so is the protection of the notes. Have some backup options available to ensure you can always recall the most accurate information.

Knowledge Check

What is a recommended method for taking notes during a pen test?

Executive Summary

It's time to wrap everything up and send in our report. This is where we focus on developing an Executive Summary for the folks that we're pen testing for. And there's a good bit of information that will be compiled.

Knowledge Check

An executive summary in a pen test report should include detailed technical information about every vulnerability found.

Challenge

In this challenge, we're going to take a look at developing our own Executive Summary based on our mock scenario.

We covered some of the information needed in our executive summary challenge and below, I have a list of things we found throughout the entirety of our pen testing.

  • a critical vulnerability was found on the forward facing web server
  • weak and/or default credentials were found during the test
  • outdated software was found
  • lack of network segmentation

Solution

Based on the information you received form the scenario, you have enough information to develop an Executive Summary for the organization that we're pen testing.

Knowledge Check

What was identified as a critical vulnerability during the pen test conducted between May 1 and May 14, 2025?

View Transcript

Beginning Pen-200

0:00Welcome back to our continuing journey of pen testing here where we kick off

0:04pin 200.

0:05And we're going to be covering a wide variety of topics all throughout this

0:09course as we start to get into advanced tool usage and also some very advanced

0:15techniques when we start to actually exploit some of the boxes themselves.

0:20First things first, let's always remember if we're pen testing, let's get our

0:24system or network owners permission.

0:26And when we do conduct that pen test, make sure it's within the bounds of the

0:30agreed upon scope. We don't want to begin in trouble as we're going out doing

0:34our exploring.

0:35But there are a few things that we're going to be covering along the way. First

0:38and foremost, like we've always talked about before, we're going to be doing

0:42information gathering where we do a lot of reconnaissance and the theme going

0:46throughout this is you're going to notice that we've and we've covered this

0:49before.

0:50The basic five phases of going into pen testing, which will get more in detail

0:55here in just a moment as we get into our first topic of note taken.

1:00And that's a part of information gathering as we continue on after we establish

1:05how do we do our notes just as a baseline. You ain't got to do everything by

1:10the way I say.

1:11We also want to go into vulnerability scanning because we don't know what to

1:16exploit if we don't have a fair idea of what it is that we're actually

1:19leveraging against.

1:20We're going to be going over a lot of the tool usage and how to actually read

1:25some of those reports and get an idea on if we can leverage something or if it

1:30's worth our actual time to try and do.

1:33Because as we know there are many different ways to scan that orange and once

1:37we get past the actual vulnerability assessment and understanding our

1:40plane and scope of how we're actually going to be pen testing an organization

1:46or an individual system.

1:47We're going to get into the actual attacks themselves and start going way more

1:51deeper into some of the tools that we introduced in the 100 and 103 courses

1:56along the way.

1:57And once we get through all that we're going to start putting all the pieces

2:01together and kind of wrap up on how we can actually come back around and fill

2:04out that executive summary for our finalize report.

2:07Now we'll be getting into the executive summary here in this particular skill,

2:11but I wanted to let you know it's good to know the note taking and executive

2:15summary stuff now.

2:17So that way we can have it as a baseline of understanding as we go throughout

2:21all the different techniques that we've learned for pen testing.

2:25Now with all that out of the way, let's go ahead and do it to it and start

2:28getting into our note taking

Beginning Pen-200

0:00One of the biggest questions that we ask ourselves inside of cybersecurity

0:04pen testing and anything business related, not just the IT portion,

0:09is why do we take notes?

0:11And it's very critical that we understand the beginning middle of end of every

0:15practice that we took along the way.

0:17And this is where it starts time into the actual pen testing itself.

0:21Pen testing is a very specific practice.

0:24And whenever we go through and conduct a pen test on an organization,

0:29it's critical that we keep notes because if a

0:33vulnerability leveraging technique goes outside the scope of what we're

0:39allowed to actually pen test, we need to keep meticulous notes on what command,

0:43what tool, basically the five W's on what it was that we did that caused that

0:50incident. Likewise, we need to make sure that we keep notes so that way we can

0:55give an basic report of what actually happened throughout the pen test itself

1:01in the executive summary.

1:02And we'll be going more into the executive summary as we continue throughout

1:06this skill. But what is it that we're actually covering inside of our note

1:12taken? Well, basically the five W's.

1:14So who, what, when, where, and why?

1:16And when we take a look at those five W's, we're taking a look at who is it

1:20that we're attacking?

1:21Basically, who is it that we're working for?

1:24Who is it that we're conducting the pen testing against?

1:27And who is it that's actually with us on our pen testing team?

1:31There's a whole lot of who involved in all this.

1:33And what is it that we're doing?

1:36Well, we're conducting a pen test, obviously, but what tool are we using?

1:40What technique are we using?

1:42What system or network scope are we actually going up against when we do

1:48that actual pen test or wouldn't we use a specific tool?

1:52When are we doing this?

1:55Because this plays a big factor in what's actually going on on the actual

1:58network itself.

1:59Let's say we're actually conducting a network scan during peak business

2:05hours.

2:05That's critical information to know because some of the traffic that we

2:09generate from our pen testing tools could potentially affect what's actually

2:15going on during regular business hours.

2:17And it could also reveal to us some vulnerabilities during peak and off peak

2:23hours.

2:23Let's say, for instance, we're running a vulnerability assessment against port

2:2880.

2:28And during the day when peak hours are at their highest, port 80 is being

2:35utilized

2:35the most.

2:36And so you would potentially see more avenues of approach when it comes to port

2:4180

2:42on that particular threat assessment, maybe, maybe not.

2:46Or maybe at night when nobody's paying attention to the web server, you see

2:49more

2:50there or less there.

2:51But this is a big part of going into wind and depending on the agreement that

2:55we

2:55have with the organization, we're actually pen testing that plays a factor as

2:59well.

3:00We may not be allowed to actually pen test during peak business hours.

3:03Good information to know though.

3:05And that's why we log when this stuff is actually happening because it all

3:09comes

3:09back to time stamps.

3:11Where are we actually doing this at?

3:12Are we doing this in the actual building itself?

3:15Are we doing this remotely from a different location that's nondescript in its

3:20nature?

3:20Or we actually doing this as a part of a collective for, let's say, Amazon

3:27cybersecurity red team and they're doing a pen test against Microsoft pick one.

3:32But the where in this is very critical too, because let's say, for instance,

3:37you

3:37decide that you want to run a pen test that's leveraging FTP servers and you're

3:43doing it from outside the network perimeter of the organization with pen

3:47testing.

3:48Well, there may be different firewall rules for internal versus external

3:53network

3:53configurations.

3:54And that's always a big consideration when we're going through and doing

3:59different

3:59types of pen testing and vulnerability assessments.

4:02You may see things that are quote vulnerable from the outside, but are

4:08completely different reporting on the inside.

4:11And why are we doing all this?

4:14Well, we're doing this because basically we're getting paid.

4:18I'm just kidding.

4:19We're doing this because we want to protect all of the systems and networks

4:23that we're being contracted to protect.

4:25And pen testing is a large part of making sure that we are fully defended

4:31against cybersecurity attacks that are in real time.

4:34Pen testers use the technique of best practice in real time in order to be able

4:41to build defenses against those threats.

4:45If we go in and we do a controlled and coordinated attack and the defense team

4:50on the for the organization going against the pen test knows about it, there's

4:55a

4:56strong possibility that they're going to be well prepared for that attack.

5:01Also, one practice to keep in mind too is that if you're pen testing yourself,

5:06you're not always going to be 100% truthful in your actual reporting because

5:11you may find it that there you may find that sometimes there are defense

5:17personnel

5:18out there that are a little embarrassed about letting people know some of the

5:21faults that they had within their own system or network.

5:23There's no shame in pen testing, but it is human nature that one of the biggest

5:29concerns is embarrassment from the system administrator's part made in

5:36some of those lines.

5:37So we usually get a third party team that comes out and does all of that pen

5:41testing because they have no shame.

5:44I have no shame.

5:45And when we go in and print out our results in executive summary form and go

5:51back to the C suite that's actually contracted us out, we're not worried

5:55about making friends on the inside of that organization.

5:58We're just there to do a job and make sure that all vulnerabilities are either

6:02identified or patched.

Timestamps

0:00Now, if there's one thing I want you to remember more than anything else when

0:03it comes to note-taking is time stamps.

0:05And I'm going to show you an example here in just a second.

0:08But the reason I point this out is because we need to make sure that we're syn

0:12ced with the actual time of the system that we're using or systems that we're

0:18conducting the pen test with and the actual organization that we're doing

0:22conducting the pen test on.

0:23And this is the same for an investigation that we would be conducting on the

0:27digital forensic side of the house.

0:30Because the time stamps don't match up or if there's not a best way to put it

0:34like a footnote inside of our executive summary that states what our timestamp

0:39scheme is, then it could be that the organization that we're conducting the pen

0:44test for thinks that we're outside of our scope in some way.

0:48Let's say business hours or peak hours are from nine to five and the

0:53organization that we're working for doesn't want us conducting pen test between

0:59nine and five.

1:00So basically, five, oh one in the afternoon, all the way up to eight, fifty

1:05nine in the morning and through the night.

1:08And if our time stamps are off and there's no indication that there is a skew

1:12of any kind whatsoever, this could cause problems when we're presenting the

1:17executive summary to those that were who are responsible for paying us.

1:21So let's take a look at an example real quick.

1:25This operating system should be very familiar by now because we're going to be

1:29using it a lot throughout this course and it is Kali Linux.

1:32So let's take a look at something real quick and that is on the top right

1:36corner, sorry, I had to turn my zoom in on you see a little bit of my OBS not

1:39apologize for that.

1:40But you see you up at the top where it says my time is four, fifteen, forty

1:44eight p.m. This is where we get a little bit outside and timescued because I

1:49want to pull this up real quick for my actual system itself.

1:55Right here and right there, you can see that it is six six TPM on the same day.

2:02Now I can verify that it's the same day if we go inside of here and just click

2:06right there. It's May 14 2025.

2:09But that's time is off from what the actual system is showing the host system.

2:16And if I'm conducting the pen test here, I need to account for that and state

2:20that there is a two hour timescue between the actual system that's conducting

2:25the pen test, which is Kali and the host system that we're on this our host

2:29system or whichever system that is that we're going to be attacking.

2:32Now, there's a couple of different things that you need to look out for when

2:36you're doing this. And that is is our system time synced with any kind of GPS

2:42are

2:43a time server, I say GPS because that's where I get my time from. We could go

2:47into properties here and go into time and date settings and you can see here

2:53that it's manually said.

2:55Configuration is manual. And then pull you real quick right there.

3:00And I'm not going to mess with that because inside of VMware, which is where I

3:04'm at right here, I'm moving it over so you could see.

3:08I'm going to right click on the actual VM that we're operating on and go into

3:11the actual settings.

3:13Experiences may vary if you're using virtual box. But if I go into the options

3:20of the actual VM that I'm on and go into VM tools, I'm going to zoom in and

3:25show you here real quick.

3:26You can see that there is a feature that's unchecked inside of the box called

3:31synchronous guest time with host.

3:34And that makes sure that our virtual machine is synced with the actual host

3:39that we're using for our virtualized environment.

3:42Now, this only goes so far as to make to ensure that the actual host itself is

3:49synced.

3:50So that's why I'm using time servers and GPS to make sure that this host system

3:54is good.

3:55So that way the actual virtual systems are good. Now, you can see here, if I

4:00click on date and time again, just like that,

4:03we have our time synced with what's actually on the actual host system itself.

4:09Move that there real quick and then move this over so you can see both at the

4:13same time.

4:14And right there, 618 on both systems, the host and the virtual one.

4:20So in a perfect world, I wouldn't have to account for any kind of time skew

4:26between the system that I'm pen testing with Cali,

4:30which is my virtual about virtualized environment and the target, which is

4:34actually going to be the host system for a lot of this.

4:36There will be exceptions, but that's just because everything's right here in

4:40the same location.

4:41It's important to remember that we're not always going to be in the same time

4:45zone as the actual targets themselves.

4:48Could be that we're a third party pen tester that's located here in Texas

4:52working against an organization for cybersecurity readiness in Eugene, Oregon,

4:58who knows.

4:59But if you're well aware of time zones, you know that Eugene, Oregon is two

5:03hours behind Texas.

5:05So when you're doing your reports and your note taking, it's always imperative

5:09to remember that there either has to be a standardized way of keeping time, let

5:13's say, like GMT or zoom time for your DOD folks out there,

5:17or you account for the time skew in your report by stating that there is a two

5:22hour skew between the target targeted systems and the ones that are actually

5:27conducting the pen test.

5:29So I just wanted to bring that up and let you know that when this is happening,

5:32time stamps are a very critical thing because that can be the make or break

5:37between staying within the scope, also reporting results correctly and seeing

5:42if the

5:43vulnerabilities that you find based on that time are in fact true, but when you

5:48found them.

5:49[BLANK_AUDIO]

Applying timestamps

0:00Number one or number two number one or number two number three or number four

0:07number three or number four

0:10You might have noticed a difference between number one and number two

0:14Being that one was just a command and the other one had the full syntax with it

0:20And number three and number four with the full syntax and output along with

0:25time stamps versus no time stamps

0:28And if you want you can go back and take a look

0:30But the point behind this is is that we want to be able to provide as much

0:34information as possible and provide those time stamps

0:36So let's add time stamps here. We are in our handy-dandy Cali box and we want

0:41to run a simple command of

0:43In-map we're doing a very quick and nitty-gritty

0:47reconnaissance to figure out what's actually out there on the network and

0:50By doing so it'll tell us what's open and what's available at that particular

0:55time of scan

0:56Well, there's that keyword again time because we want to make sure that we are

1:01within

1:01Compliance of our scope and our rules of engagement to make sure that we are

1:06doing everything when we're allowed to do it

1:08If there are any time constraints

1:10So if I zoom in for you here real quick, you'll notice that there's no time

1:15stamps whatsoever

1:16and even if we run a simple command, let's say in-map and

1:22We're just going to do a quick scan real quick. We could hit enter on this and

1:26we can see that

1:27Let me pause and zoom in for you there real quick

1:29There is a timestamp on the actual in-map command them itself

1:33But there won't be actually anything in the actual terminal other than what's

1:38in that command or tool that you're using at that time

1:41So now there are different ways to do this and what I like to do when I'm

1:45getting into want to keep track of every

1:48Thing that's going on to the second I can actually

1:52Incorporate time stamps inside of the channel itself to make things a little

1:56bit easier on me now

1:58I've cleared the screen and we're gonna walk through this together because I

2:00want to make sure that we all

2:01Can follow along and make sure that we're installing tools correctly first and

2:05foremost

2:06I want to make sure that we have a pseudo apt

2:08update that's ran to make sure that we have all the available packages to us

2:14from the Cali repository

2:16Now I've done this offline and already did all of our upgrades

2:19So this shouldn't take too terribly long now. I've cleared so we're gonna go

2:23ahead and do a pseudo apt install more utils

2:27and

2:28You can see there that it's gonna add a couple of different things to it

2:32But yes, we want to go ahead and install that and timestamp is one of the

2:35things that's included inside of the morning tilt

2:38And we'll be able to pipe it with some of the commands that we're actually

2:42using

2:43Such as in map now obviously that didn't take too long

2:46But I want to give you an example real quick

2:48We're going to do an if config - a and pipe in

2:52TS and you can see here that we get time stamps now

2:57With every line of output that's going through to include the actual initiation

3:02of the command itself

3:04Which was 18 to be 859 now if I run this by itself

3:08if config - a you can see that there are no time stamps there and

3:13that

3:15Just to give you a compare contrast now this comes into play a whole lot better

3:20when we go into in map and

3:21We ran it while while ago

3:24But now we're going to pipe a TS on the end of it and you can see here for a

3:29fact

3:29I'm gonna stop and zoom in for you real quick not only do we get the actual

3:33timestamp on the end of it itself

3:35But at the beginning of it we get the full

3:38formatted to our system timestamp May 14 659 32 seconds and

3:43Starting in map 7.95 and you'll notice that on the end map

3:48It doesn't actually have the seconds on there now is that getting two in the

3:51weeds on the time stamps?

3:52Maybe but for me it makes sense and if I zoom out you can see that

3:58The the entire program ran it took about four seconds to complete a quick scan

4:03of the overall network

4:05And we have time stamps to prove every little thing that happened

4:09so when we start going and comparing two logs on the network for our

4:13Roundup meeting with the actual

4:16Administration teams they can actually go through in their network logs and see

4:21at that particular time

4:22Based on timeskew if there is any and see if that lines up with their systems

4:28If not it could be an indication of the vulnerability or if it does yes

4:33they got it and it was duly noted.

Note taking

0:00Alright, so we've got time stamps, commands, got the history configured to be

0:04able to

0:05include time stamps, then over some of the things that we need to be on the

0:08lookout for

0:09for time skew.

0:11Let's get into taking notes.

0:12And this is going to be a big part of everything else we do all throughout the

0:16skill, so I

0:16kind of want a hammer on this now instead of having to nickel and dime it all

0:20the way

0:20throughout the entirety of the course.

0:23So let's go back and remember.

0:28The five phases of pen testing and they go down to reconnaissance, scanning,

0:34vulnerability

0:35assessment, exploitation and reporting.

0:39Now I know what you're thinking important has its own section that should be

0:42where all

0:42the notes are, right?

0:44Wrong.

0:45We need to make sure that we're keeping notes the entirety of the time because

0:48when we do

0:49get to reporting, it's going to be that executive summary that we're going to

0:53cover in a little

0:53bit, but we also need to make sure that with the notes that we do have that we

0:59either don't

1:00repeat a step by accident, don't mess up a step by accident or do anything else

1:03by accident.

1:05And during the reconnaissance phase, we're going through and basically scoping

1:10out the

1:10entirety of what's entire within the organization that's within our rules of

1:16engagement.

1:17This is our time for us to gather that preliminary information.

1:22And the note taking comes critical because there may be items or systems within

1:27the organization

1:28that were pen testing that don't need to be touched.

1:31And that would be something that we need to make note of.

1:34And I've said this before in terms of like, make a note of it.

1:39This is what we're actually talking about now because if there's a particular

1:43target

1:43system out there that does not need to be touched and it was inside the rules

1:47of engagement

1:48and we didn't make a note of it, that could really come back to bite us in the

1:52butt because

1:52it's either going to get us canceled out of a contract, we may have to recoup

1:57some

1:57costs and that does happen.

1:59When we're actively scanning, just like we saw in the N-Map earlier, there's

2:03going to

2:03be a lot of information that comes back and the scope within the rules of

2:06engagement can

2:07go even deeper.

2:09We're allowed to attack some ports but not others.

2:12We're allowed to attack some systems based on time and not others.

2:16And the notes that we get during the scanning process basically allow us to be

2:20able to keep

2:21track of the different vulnerabilities, the different systems out there and

2:26also be able

2:27to know what kind of a service plane that we're attack surface that we have for

2:34those

2:34particular systems within the scope of our pen test.

2:38So the notes for this one would be if you wanted to imagine real quick, a

2:43spreadsheet

2:44could be something like this.

2:45One nine two one six eight zero dot one through two fifty five and then based

2:50on the ports,

2:51you know, the commonly found ports are the ones that you want to attack or the

2:55ones that

2:55are open, you could say zero dot one had port 80 open and 443 and go through

3:01line by line.

3:02Instead of having to rerun thing all the time or rerun your scanning.

3:07Now you will rerun scans as you go throughout your pen testing process because

3:12certain systems

3:12do different things based on different times of day and different activity with

3:17the user.

3:17But it's good to have a baseline of notes taken on the side to make sure that

3:21we're

3:21all in line with this.

3:23And the same thing goes with vulnerability.

3:24If you have a specific system out there that has a vulnerability report or

3:30different

3:30whole network systems out there, you can actually go through the actual

3:35vulnerability report

3:36itself and go through and make notes on it of hey, I scanned it at this time,

3:41which will

3:41be in the vulnerability assessment itself or you can go through and note on

3:45there, hey,

3:46I've ran across this vulnerability before and I've leveraged it with Metasploit

3:50using

3:50this plug in and just something to keep note on the side of.

3:55Exploitation kind of in the same vein of this, you know, what results are you

3:58getting

3:59back and did you find something else during the exploitation that you wanted

4:02nine deeper

4:03on and you can make a note of that.

4:05And then all of it gets pulled all together and tallied up between you, me and

4:10the team

4:10that we have together to be able to build out that executive summary.

Note taking in use

0:00Now, I just want to hit on one more thing before we start even noting it into

0:03our executive summary of the wrap up of the skill.

0:06And that is, where do we take notes at?

0:09Well, this is more of a shooter's preference thing.

0:12All I'll say for sure is that there needs to be a surefire way of backing that

0:18up and being able to call upon those notes for reference later on, be it an

0:23investigation or verification or whatever the case may be.

0:28Now, my method of taking notes is usually pen and paper and something as simple

0:34as a regular notes booklet is and I keep one of these per

0:40pen test or investigation that I use.

0:43And the reason I do this is because some of these, if you can see up at the top

0:48right there, it has month and date that I could just simply circle on there and

0:54the title up at the top.

0:56Now, I put bullet points in there, things like I walked up to the system, I

1:01began my pen test.

1:03This is the tool that I use, this is the command that I use.

1:06Now, for the purposes of this course and being that we are computer based

1:10training online, I know that this is not always applicable to the things that

1:15we do because I'd have to be able to write and scan every page that I took

1:20notes on.

1:21That being the case, as you can see over here on this screen, I have a Word

1:25document opened up and I just want to pull that over here in just a second and

1:30show you a couple of tricks real quick.

1:32So here I am in Microsoft Word and I promise that this is elbows at hand, but

1:37it comes in handy if you want to use it.

1:41So I'm going to go to file and go down to options real quick and make sure that

1:46in my customization river ribbon that on the right side, I have right there

1:51developer checked for us to be able to do this.

1:55Once that's done, you should be able to go to the developer tab, which is what

1:59I'm on now and up on the top left is I'm going to zoom in for you real quick is

2:03the macros button.

2:05Inside of macros, you can see that I have one in there called timestamp and I

2:09've exported this and I want to put it in as an attachment right below this

2:13video.

2:13Go into edit it. You will see that I just put in a simple selection there that

2:19allows me to be able to do the timestamp of your month day with the actual time

2:23itself.

2:24By all means, with this as you want based on how you are your organization does

2:30. But the reason I've pointed this out is because I also go through and go into

2:36file.

2:36Options.

2:38Customize ribbon and then go into customize keyboard shortcuts. And if I go all

2:45the way down to macros on the left, you'll see that I already have one set for

2:50timestamps, which is that macro we just created.

2:53Along with all control one as being my actual keyboard shortcut to that. So

2:59long story short, if I go inside of word now and specifically inside of this

3:04document or I have a separate word overall.

3:07But if I go through and say all control one. There's my actual timestamp right

3:14there and I can say opened case or pen test.

3:19And then and then all control one again and then say.

3:25Assigned Eric to pen test.

3:33And you get the idea is we can go through and hit the timestamp anytime that we

3:37need on our keyboard. So that way, as we're making notes and annotations about

3:42different tools that we use different things that you ran across.

3:45We can put the actual timestamp in there correlate with what we've learned

3:50inside of Cali by going through and comparing it to the actual bash history or

3:55even in the terminal itself.

3:58And this allows us to be able to alleviate times to all together. So that way,

4:02when we do get to our executive summary, we can nip this in the bud and make

4:06sure that everything's all on the same sheet sheet and use it.

4:10We can also annotate in our notes here if there's a time zone difference or if

4:15there's a problem with the virtual machines.

4:18Specifically with the other site, not always have an access to NTP or yeah.

4:25Now you may think that's a 10 bit silly, but I'm here to tell you that not all

4:29networks out there have NTP or

4:31GPS available to them for time synchronization. You will run across different

4:37networks, specifically in sign of DoD

4:40That are secret and above that don't have access to regular internet resources.

4:46And there are GPS and NTP solutions on those specified networks of class

4:50ifications. However, they're not always readily available, especially in I give

4:57you a little bit behind the curtain here in those mobile command environments

5:00where you don't always have access to the rest of the actual

5:05network. So if you set everything up and you're running internally, they should

5:10have all their systems sync to the domain controller or a central point within

5:15that network.

5:16And if you're brought in the pen test, you need to make sure that whatever time

5:20it is in real time,

5:21along with the notes of what time it actually shows on those individual systems

5:26, because in those closed network scenarios,

5:30you will see timescue happen all over the place. And with the advancement of

5:36CPUs and GPUs and all the other fun parts that are a computer nowadays,

5:41there is still a little bit of timescue the longer those systems are left on or

5:46being utilized. So it's not like that day. It's not as bad as the days is

5:51286, 386 and 46 and having to manually set your time at Pascal. Yes, I remember

5:57those, but it does happen over time and it can cause discrepancies within your

6:02reporting.

Executive Summary

0:00We've been over how to take notes, make sure that all of our time stamps are

0:03aligned.

0:04Basically, we're building out references for our final executive summary.

0:08Now, I want to point out that in executive summary, you will not have all the

0:13nitty-gritty details of every vulnerability exploit or problem that was found

0:19throughout

0:19the course of our pen test. An executive summary is really just for the C-suite

0:24or

0:26anybody in charge of the organization or network that we're actually doing the

0:31pen test on.

0:32It's a synopsis or a very brief summary of what's actually happened throughout

0:38the course

0:39of our pen test. Key bullet points is the topic here. We don't want to

0:45overwhelm everybody

0:46throughout the executive summary, and we want to try to keep it as short as

0:50possible.

0:51Now, generally, executive summaries are going to be a page or two. That should

0:56be enough information

0:58right there to tell you that only the most important information is only going

1:03to be inside of the

1:04executive summary. Now, as we go through this, I kind of want to point out a

1:08couple of different

1:09areas real quick, and that is, first, starting off, we need to have an

1:13engagement overview.

1:15This will basically be the opening paragraph of our executive summary that

1:19explains

1:20what exactly happened and when did it happen. So, how long did our pen test

1:26take?

1:26When or who did we pen test against and what were we looking for? Followed

1:31right after that are

1:32going to be our key findings. Just for me, and you may be a little bit

1:37different based on

1:39space available within your executive summary or how detailed you want to go,

1:42I generally try to keep this between three and four of the biggest points taken

1:48away from

1:49the actual pen test itself. Again, we're not trying to get too far into the

1:54weeds of what

1:55actually happened, but let's say throughout the course of our pen test that we

1:58discovered that

1:59there was a serious password breach on a critical server within the

2:04organization that were pen

2:06test against. That's something that needs to be highlighted, especially if it

2:10has something to do

2:11with PII or information that is federally regulated, like HIPAA or FERPA or

2:17something along those lines.

2:19And inside of those different three or four areas, we want to bring out the

2:24biggest things that

2:26need to be addressed. Along with those could be like, let's say we did a

2:31username and password

2:33test on the actual network itself against active directory and we found that a

2:38bunch of default

2:39passwords were being utilized or that there were some weak passwords all across

2:44the network,

2:45so easily guessed and things like that. It might be something that you want to

2:49bring up. So many

2:50accounts, XX accounts had the weak passwords that were able to be penetrated

2:55and exploited and

2:57basically just key points. We don't want to go too deep on this one. This is

3:03going to be followed

3:04by our risk assessment and this is just a quick paragraph of where do we as pen

3:11testers see the

3:12overall organization, not one particular system, not an idea of multiple

3:18systems,

3:19but the overall organization itself, low, medium, high, critical, whatever the

3:24case may be, because

3:25it's also possible that you can run a NASA scan and find a high or critical

3:31vulnerability within

3:33the organization and this is an accepted risk by that network or system owner

3:38that's already been

3:39identified as an exception inside of our scope and rules of engagement. If that

3:45's the case,

3:45then that shouldn't really be included here. We just want to have a quick, hey,

3:51where do we see

3:51the organization? Overall, I rate you as medium. There are a couple of

3:55different things on there

3:57that you should take a look at and that should really be it. We're then

4:02followed up by the

4:04recommendations section. What are some quick tidbits that the C-suite can

4:09identify to issue out

4:12orders to the tech team to be able to remediate issues that were found within

4:18the course of our

4:19pen test? These would be very quick and to the point. You don't want to go into

4:24the actual technical

4:25details. For example, let's say those passwords that we were talking about

4:29earlier, we just want

4:31to be able to identify that as a recommendation, maybe users should go in and

4:36strengthen up their

4:37passwords. Maybe the administration team can implement a policy of minimum

4:43strength passwords,

4:44something along those lines, not the actual CB or the configuration idea inside

4:51of the system

4:52itself. Lastly, we wrap up with the conclusion and this is going to be a quick,

4:58this is what happened.

5:00We revealed many different things that were wrong with your organization and we

5:04're going to recommend

5:05a follow-up or not and when that follow-up should take place. For me, on my

5:12executive summaries,

5:14I'm always going to have an included section at the very bottom as well. This

5:18is basically an old

5:20DoD habit because for memorandums for record or anything like that, you'll

5:26always have an

5:27included section at the bottom. Now it's good to have an executive summary be a

5:31synopsis of

5:32everything that happened really quick but also include the detailed information

5:38such as the

5:39vulnerability assessment such as the actual network scan that we did throughout

5:43the pen test itself

5:45and some of the CDE reports of the different things that we found that were

5:49causing or are

5:50raising attention to earlier on in our executive summary. Now all this is

5:55pretty much straightforward

5:57and I will give you an example in the challenge because I just wanted to go

6:02over some of the

6:03different things that we needed to consider when it comes to executive summary

6:07and that's

6:07going to take us into our challenge.

Challenge

0:00It's challenge time and this one we're going to be making an executive summary.

0:04Now again, it's a summary. It's not supposed to be a dissertation, but I'm

0:09going to cover some of

0:10the information here and put some bullet points right below this video so that

0:15way you can compile

0:16together how you at home would like to compile or present your executive

0:21summary. One thing I

0:23really want to stress here is that there's no single answer for an executive

0:27summary.

0:29Different folks have different ways of presenting information and putting

0:33together and preparing

0:34an executive summary for a pen test, but the idea remains the same with the

0:39five areas that we

0:40covered in the previous portion of the skill. Now between one May and 14 May

0:462025, we conducted a

0:48pen test against CBT nuggets and there were a bunch of areas that we were

0:52looking to test out against

0:55such as systems that could lead to credentials that could lead to unauthorized

1:02access, maybe even

1:03some data that was being exposed and see if we could cause disruption services

1:09based on some of the

1:11exploitation practices that we're going to be trained up in throughout this

1:15course.

1:15And some of those findings that we had are going to be reported in our key

1:21finding section. Now I

1:23have again right below this challenge video some of the findings that we had so

1:28you can expand on

1:29them at your leisure inside of the executive summary. Now based on this

1:33information that I've

1:35given you so far, we have a risk assessment that needs to be made and I'm going

1:41to let you choose

1:42how you want to be able to identify this as a low, medium, high or critical. I

1:48have my own which

1:49will be coming up here in the solution and we'll review it together. And then

1:53whatever recommendations

1:55that you would like to make and they usually are tied to the key finding. So if

1:58you have key

1:59finding number one, you should have recommendation number one and they should

2:03kind of be tied together.

2:05And then whatever your conclusion is and if you want to be able to sign and

2:09validate your executive

2:10summary. So now that you have that information and what you see right below

2:14this video, let's go

2:15go ahead and do it to it and I shall see you in the solution.

Challenge

0:00It's solution time and I wanted to show you the executive summary that I've

0:04come up with based on the information that we had in the challenge.

0:06Remember, we had the bullet points above and some of the key information in the

0:11actual challenge video itself.

0:13So let's take a look at how I attack this one.

0:16Here we are in my executive summary PDF version of this below so that way you

0:20could use it as a template.

0:22I don't mind.

0:23And there are many other templates out there that you could take a look at.

0:27But the key factor here is that we have all five areas discussed and we start

0:32out with our overview, which is between one May in 14 May 2025.

0:37We did a pen test on CBT nuggets and we basically just gave a five W's of what

0:43happened there.

0:44We move on into the key findings and that was exactly what I put inside of the

0:49challenge bullet points.

0:52And again, you don't have to word them the exact same way I do and I don't want

0:56them the exact same way anybody else does just whatever fits based on the

1:00organization and whatever templates that you require to use or maybe achieve

1:04your preference.

1:05Who knows.

1:06But these are the four areas that we found and after that we put together a

1:11risk assessment and this one I rated it as high.

1:15And the reason for this is mostly due to the vulnerability inside of the web

1:20facing web server along with the amount of user credentials that were either

1:26simple or default passwords.

1:28Now, I do want to take a side here real quick and point something out and that

1:33on the DoD you know who you are.

1:36There are many systems of record that are implemented that have default

1:41passwords assigned to them and whenever I conduct pen testing for DoD or when I

1:46actively did it full time for the army.

1:49This was always a major problem. So if you're with the DoD and you are using

1:53let's say CPC or any kind of command and control software change the default

1:58password because I'm tired of popping them.

2:02So yeah, take that, but our risk assessment is overall high due to those

2:06default passwords and that vulnerability on the web server, which leads us into

2:11the recommendations on how we would actually go about changing this up.

2:15Now these are quick and to the point how I would actually go through

2:19immediately patch.

2:22Go in and take care of that insecure code that's inside of that web server, put

2:27in a group of policy or just find a way to enforce those strong passwords

2:31within the organization.

2:33And then we wrap everything up with our conclusion and my conclusion is that

2:38several areas required our new intention to strengthen the organizations

2:42security posture are needed and I want to come back in 90 days.

2:46And my signature block along with on the bottom left and what's in there

2:50included network scan report vulnerability assessment user and password report.

2:55That way, if after the executive summary is presented to the C suite upstairs

3:00that way the folks in the tech office and I can pull to a side and go into some

3:05of the nitty gritty nerd talk that goes along with this.

3:09Now this isn't trying to insult anybody inside the C suite, but most of times

3:14when we put together an executive summary or do any kind of tech work for an

3:19organization that has a C suite involved.

3:21More often than not that C suites not going to be to in the weeds are hip to

3:27what it is that we as techies do within the organization.

3:32Anyways, you ever form. So it's always good to make sure that the executive

3:36summary is written to where anybody can pick it up within any organization and

3:41understand the base principles of what it is that needs to be done or addressed

3:45inside of that organization after we're done with our pen test.

3:50So now that we have all of our note taken out of the way and have an

3:53understanding of what it is that the baseline is for the rest of this course.

3:58And we know how to properly record it up to those executives upstairs. Let's

4:03start getting into some of the breaking of testing of things as we continue out

4:08through pin 200. I hope this has been a formative for you and I'd like to thank

4:12you for viewing.

4:13[BLANK_AUDIO]

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