Project: Penetration Testing Report
(20 Points)
You have been hired as a junior security consultant and have been tasked
with performing an in-house penetration test to demonstrate your readiness
to support the audit of a large corporate client that has employed your firm’s
services. Conducting a penetration test consists of 1) planning the test, 2)
preparing your test tools, 3) performing the test, 4) analyzing the data, and
5) writing up and communicating your findings. The project will document
your notional penetration test.
Your project will be submitted in four sections. The final deliverable will
include all combined sections:
 Pre-Test: Deployment of attack tools and victim host (Week 2)
 Testing (Mapping and Scanning): Mapping the target environment
and conducting a vulnerability scan (Week 4)
 Testing (Exploitation): Gaining Access through a vulnerability
identified during the vuln scan (Week 6)
 Analysis and Reporting: Communicating findings and providing
mitigation recommendation (Week 8)
Supporting Details
The purpose of this project is to evaluate the student’s ability to:
 Build and deploy an attack OS (Kali Linux or other similar operating
system (OS))
 Configure and deploy a victim host (Metasploitable, Broken Web
Apps, Mutillidae, other exploitable OS or virtual machine (VM))
 Conduct a vulnerability scan
 Research a hardware or software vulnerability
 Discuss how the vulnerability can be exploited
 Exploit the vulnerability
 Evaluate the risk posed by this vulnerability
 Provide a recommended compensating control to mitigate the
Students may choose to submit the project using one of two options – each
option has pros and cons that students should evaluate before making their
1. Local Lab: Requires access to a dedicated computer in which
students have sufficient:
o access (continued access to the same machine for the
duration of the course)
o permissions (administrative permissions to install software)
o storage (minimum of 30 GB available to the student for VM
o memory (minimum of 8 GBs)
o bandwidth (downloading large VMs can take considerable
time even with high-speed Internet connections)
2. Remote Lab: Utilizes the online lab environment used to complete
the weekly course labs
Part 1 – Pre-Test: Deployment of attack
tools and victim host (Week 2)
PROJECT SECTION 1 DETAILS: The first part of your project consists of
preparing and deploying your testing tools (the attack OS) and the
vulnerable host that will serve as your attack target. Instead of requiring the
use of two physical machines, we will utilize one physical machine and we
will leverage virtualization software to install a hypervisor (VirtualBox,
VMware, etc.) along with two (2) “guest” operating systems. For those new
to virtualization, we are simply using our “host OS” (Window, Mac, Linux) and
installing a virtualization “software application” that then allows us to run
multiple OS’es on our “host OS” very quickly and easily. Many options
exist that provide virtualized solutions, e.g., cloud-based (Amazon
Web Services, Microsoft Azure, DigitalOcean, and many, many
others) or local instances on our machines. Some hypervisors run as
the “host OS” (‘bare metal’ like VMware ESXi – common in enterprise
environments) or as hosted applications like VMware Fusion/Workstation, or
Oracle VirtualBox. First you decide which “free” virtualization software you
want to install (VMware or Oracle) – some may already have a preference,
feel free to explore both options. If you are undecided, go with VMware.
As mentioned earlier, you have two options to choose from:
Option 1 – Local Lab
1. Virtualization Software. Choose your virtualization software
(either works fine and they are both free):
 VirtualBox:
o (Links to an
external site.)
 VMware Workstation Player:
2. Attack OS/VM. Once your virtualization software is chosen, choose
an attack OS to download. You will use Kali Linux in the lab
environment and would likely be the most comfortable with that.
However, you may download any “attack OS.” Other options
include: Parrot OS, BackBox, BlackArch (advanced only – save
yourself the pain and skip this one), and many others. Note: It will
be much easier to download a pre-built VM instead of the .iso image
option. Additionally, the pre-built images are specific to the
virtualization software that you are using so choose accordingly.
3. Vulnerable Target OS/VM. You will need a victim machine to
target and exploit. Download a virtual machine that you can
attack. There are many options that are designed to help students
practice their skills and learn to exploit vulnerabilities in an
approved, educational manner. Keep in mind that these are
inherently vulnerable and designed to be relatively easy to exploit.
A recommended best practice is to not allow other machines
outside of your “virtual network” to be able to communicate with
them. There is a “NAT” network setting within your
virtualization software that helps to isolate your “lab”
systems from the other devices on your local area network.
Many options exist, but here are a few:
 Metasploitable (also includes many of the ones below – the same as
what is in the InfoSec labs). There are a few versions out there – go
with “Metasploitable2” – it can be downloaded
table2/ (Links to an external
site.) or
2017.html (Links to an external site.)
 OWASP’s Broken Web Apps (includes
wnload (Links to an external site.)
 DVWA (Web
.zip (Links to an external site.).
 Bad Store (Web
Application):,41/ (Link
s to an external site.)
 VulnHub: Many options exist here – somewhat like a “capture the
flag” with near limitless possibilities with new ones being added all
of the time (Note: I would save these for after the class project –
more for fun) (Links to an external site.)
4. If you need additional help installing Kali, please review Kali Linux
Revealed for step-by-step instructions. There is also a course video
during Week 2 that is very helpful
Option 2 – Remote Lab
The previous option is definitely a lot of fun and helps develop a better
understanding of the underlying architecture but, unfortunately, may not be
a viable option for you depending on your circumstances. Option 2 can be
done without having to install any software and consists of the student
logging in to the InfoSec Learning labs to complete the project for the
remainder of the project sections. In lieu of downloading , installing and
configuring software, Option 2 Part 1, requires research into an online cloud
hosting provider and the deployment of a virtual private server. This option
also has some flexibility.
 Option 2A: Research and choose a cloud hosting provider and
deploy a virtual private server that you can remotely access and
configure. Install any “free” operating system on the cloud server.
Typically, any Linux OS can be freely deployed without charge.
Most, if not all, of the cloud hosting providers will require a credit
card or PayPal account to verify identity and may charge a nominal
fee ($1 or more). The submission requirement for this option is to
take a screenshot of your newly created VPS with an open terminal
window echoing (printing to screen) your name and date simply to
show that you created it.
 Option 2B: Research three cloud hosting providers and compare
and contrast their offerings in terms of a solution that you could use
if you were to conduct your penetration testing from their cloud
services. Consider costs for computing time, storage, access,
security, etc. The research paper should be 1.5 – 2 pages in length
with a minimum word count of 750 words.
SCANNING): Mapping the target
environment and conducting a
vulnerability scan (Week 4)
PROJECT SECTION 2 DETAILS: The second part of your project has two
parts. You may choose either Project Lab Option (“Local Lab” or “Remote
Lab”) below to complete the following requirements:
 Part A: Identifying the target system through network discovery
using at least two network discovery/mapping tools (e.g., Nmap,
Netdiscover, Arp-scan, etc.) to identify networks and targets.
Identify what ports, services, and versions of software are running in
the network environment.
 Part B: Additionally, you will need to complete a vulnerability scan
against your target host to identify vulnerabilities that you can then
use to exploit to gain administrative/root access in the following
project section
Option 1 – Local Lab
Choose any of the tools within your chosen Attack VM (Kali, Parrot OS, etc.)
to map your network following the Part A requirements
Choose any vulnerability scanning software to download, install and
configure (Open VAS, Nessus, etc.) complete Part B. You should be able to
find free “personal/home use versions).” Configure a scan to run against
your target host. If your target host is a deliberately vulnerable machine,
you should find plenty of “critical/high” vulnerabilities to choose for your
attack in the following project section.
Option 2 – Remote Lab
You may choose to complete this portion of the project using the Infosec
Learning Lab “Remote and Local Exploitation.” No software downloads are
required, so just configure your tools and complete the scans. Follow the
requirements in the Project Section 2 Details.
Part 3 – Exploitation: Gaining Access
through A vulnerability identified during
the vuln scan (Week 6)
PROJECT SECTION 3 DETAILS: The third part of your project requires you
to exploit a vulnerability of your choosing based on the previous section’s
scanning. The exploit should be through a Metasploit Module or other opensource/commercial tool or custom script/code. Select your vulnerability
carefully. You should thoroughly research your vulnerability before you start
to exploit it – which is the same process you would use in a professional
capacity. The vulnerability MUST RESULT IN GAINING SYSTEM/ROOT
ACCESS on the target host. Compromised credentials (including no
password or weak password) is not a sufficient vulnerability to exploit.
During the course labs, you will have completed labs that require you to
exploit a vulnerability. You must choose an exploit that we have not done in
class. I suggest doing a web search on “Metasploitable Walkthrough” for
additional ideas on Metasploit modules that could be used (if you have
selected Metasploitable as your vulnerable target), or research vulnerabilities
specific to your vulnerable framework. Keep in mind that your vulnerability
should have been flagged during the vulnerability scanning portion.
Option 1 – Local Lab
Depending on your chosen vulnerable target host, you may have many more
vulnerabilities to choose from. I recommend that you keep it simple and
stick with a vulnerability that is well documented so there is sufficient writeups and posts to follow. With that said, creativity and rigorous exploit
research is always welcomed and appreciated.
Option 2 – Remote Lab
Your choices are surprisingly not limited here. There are, of course,
vulnerabilities in some of the web applications that will not show up in a
vulnerability scan with a tool like Nessus due to what Nessus is actually
looking at. With that said, web application vulnerabilities are a bit more
complex than some of the other software vulnerabilities that are well
documented for Metasploitable. I recommend you stick with a welldocumented vulnerability.
Part 4: Analysis and Reporting:
Communicating findings and providing
mitigation recommendation (Week 8)
PROJECT SECTION 4 DETAILS: The fourth part of your project requires you
to provide a well written report documenting your results and reporting your
findings and recommendations. The report should include the following:
 Vulnerability Research: Research the vulnerability and discuss
the specifics. What does the software do and why does the
vulnerability exist? You must explain the technical aspects of the
vulnerability to get full credit. Remember: This is the research
portion. Learn about the vulnerability and discuss it in your own
words – do not simply copy and paste.
 Vulnerability Analysis: Describe the vulnerability in terms of
complexity, access, privileges required, vulnerability scoring, etc.
Reference the National Vulnerability Database (NVD) scoring.
Explore the links associated with the vulnerability in the NVD. This
typically provides a lot of high-level and low-level technical details.
The difference between this section and the vulnerability research
section is that this should be specific to the implementation of the
software and the existing environment. For example, does the
vulnerability exist across all instances of this software or is it
specific to a configuration or installation stack? Each vulnerability
should have a CVE and CVSS score that will help provide additional
 Vulnerability Exploitation: Discuss the steps that were taken for
the exploitation. Please provide the configuration of the script or the
settings of the tool. To receive full credit for the exploitation, you
need to show system-level access, root-level access, or admin-level
 Testing Detail: You need to show elevated access. If you
cannot show root (or privileged access), choose another
vulnerability. Run the following commands on the target
machine once you have fully compromised it:
o id
o hostname
o run the hostname command on the compromised
machine and then re-run the hostname command
(see figure below)
o whoami
o One of the following commands: [ ifconfig ] |
[ ipconfig ]
Figure 1 Evidence of Exploitation
 Risk Assessment: Use this area to discuss what the risk
represents to an organization. Would it change the risk if it were on
a public-facing server as opposed to an internal server? What
happens if this exploit were successful? Assume that the vulnerable
software would be installed in a business environment, not your
home lab network. Discuss the a few different risks that would be
dependent on where and how the vulnerable software would be
installed across the organization.
 Mitigation and Security Control Recommendation: Discuss
how you fix this vulnerability. Can you patch it? Are there additional
security controls, protections, or sensing mechanisms that could be
installed to lessen the impact of an attack?
 The proposal document should be 7 to 10 pages, conforming to APA
standards (double-spaced).
 At least two authoritative outside references are required. These
should be listed on the last page titled “References” – which does
not count toward your overall page count.
 Screenshots are required for each major section – any sensitive
information may be obfuscated or redacted).
o Screenshots will be no larger than 1/4 page. The text
within the screenshot should appear readable so avoid
taking “full screen” captures. Capture only the appropriate
detail. Terminal command output should be no smaller
than an “equivalent” 12-point font size (similar to the font
in this document).
o Screenshots and images do not count toward the overall
page count. The project may extend into multiple pages
depending on the number of screenshots
o Clear screenshots should be used. There are numerous
options available to take screenshots. Use Google, or go to for various options. By
no means should you take a picture with your smartphone
or camera and paste in.
 Appropriate in-text citations are required.
 This will be graded on quality of the research topic, technical
demonstration/write-up, the content quality, use of citations,
grammar and sentence structure, and creativity.
 The paper is due during Week 8 of this course.
 This paper should effectively describe the vulnerability, risks and
recommendation in a manner that will allow TECHNICAL readers to
understand the vulnerability, risk and mitigation. The course
material and research should provide you with the right level of
technical understanding.
 Format: The paper must contain clearly labeled headings for each
major section: Network Mapping, Vulnerability Scan, Vulnerability
Research, etc.
 (Links to an external site.)
 Note: If you’ve never used Microsoft Word’s “References” feature to
manage citations, please invest some time in learning how to do
this. You’ll be glad that you did.
4940-9c69-342c289fa2a5?ui=en-US&rs=en-IE&ad=IE (Links to an
external site.)
 Ensure that you cite your references in the text when you are using
material from the reference.

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