Problem statement:
In this project, students will conduct a simulated penetration testing engagement to assess the
security posture of a target system or network or web application. The project will involve
performing reconnaissance, identifying security vulnerabilities, exploiting weaknesses, and
providing actionable recommendations to enhance security defenses. Through hands-on
exercises and practical scenarios, students will gain experience in penetration testing
methodologies, tools, and techniques, as well as develop critical thinking, problem-solving, and
communication skills in a simulated cyber-security environment.
Project Objectives:
1. Prepare a web application project and host it
2. Apply penetration testing methodologies, tools, and techniques to identify and exploit
security vulnerabilities on the web application
3. Generate testing reports
4. Assess the effectiveness of security controls and defenses in mitigating cyber threats and
attacks.
5. Provide actionable recommendations for improving security posture and addressing
identified vulnerabilities.
Project Tasks:
1. Scope Definition: Define the scope and objectives of the penetration testing
engagement, including the target system or network, rules of engagement, and
permissible testing activities. Identify the goals, constraints, and limitations of the
simulated penetration test to ensure alignment with project requirements and objectives.
2. Reconnaissance and Information Gathering: Perform reconnaissance activities to
gather information about the target system or network, including network topology,
infrastructure components, operating systems, services, and applications. Use open-
source intelligence (OSINT) techniques, network scanning tools, and reconnaissance
frameworks to enumerate targets and identify potential attack vectors.
3. Vulnerability Assessment: Conduct vulnerability assessments to identify security
vulnerabilities, misconfigurations, and weaknesses present in the target system or
network. Utilize vulnerability scanning tools, web application scanners, and manual
testing techniques to identify common vulnerabilities, such as misconfigured services,
outdated software, and insecure configurations.
4. Exploitation and Post-Exploitation: Exploit identified vulnerabilities and weaknesses to
gain unauthorized access to the target system or network. Perform penetration testing
activities, such as network exploitation, web application attacks, privilege escalation, and
post-exploitation techniques, to simulate real-world cyber attacks and assess the impact
of security compromises.
5. Documentation and Reporting: Document findings, observations, and
recommendations throughout the penetration testing engagement, including detailed
descriptions of vulnerabilities, exploitation techniques, and recommended remediation
measures. Prepare a comprehensive penetration testing report summarizing assessment
results, risk ratings, and actionable recommendations for improving security posture.
6. Presentation and Debriefing: Present the findings and recommendations from the
penetration testing engagement to stakeholders, including project sponsors, clients, or
peers. Conduct a debriefing session to discuss assessment results, lessons learned, and
insights gained from the simulated penetration test, and solicit feedback for future
improvement.
Assessment Criteria:
Technical Competence: Effectiveness of penetration testing methodologies, tools, and
techniques employed to identify and exploit security vulnerabilities.
Critical Thinking Skills: Ability to analyze and interpret assessment results, prioritize
findings, and recommend remediation measures based on risk severity and impact.
Communication and Presentation: Clarity, professionalism, and persuasiveness
demonstrated in presenting findings, recommendations, and insights to stakeholders.
Documentation Quality: Completeness, accuracy, and coherence of penetration
testing reports, including detailed descriptions of vulnerabilities, exploitation steps, and
mitigation recommendations.
Deliverables:
1. Penetration Testing Engagement Plan (including scope, objectives, and rules of
engagement).
2. Penetration Testing Report (summarizing assessment findings, vulnerabilities, and
recommendations).
3. Presentation Slides (communicating project outcomes, analysis findings, and
recommendations).
4. Debriefing Notes (reflecting on lessons learned, challenges encountered, and areas for
improvement).
1. All
2. Penetration Testing
How do you scope
and plan a web app
pentest project?
Powered by AI and the LinkedIn community
Define the objectives
Gather information
Choose the tools and methods
Perform the testing
Analyze and report
Here’s what else to consider
Top experts in this article
Selected by the community from 56 contributions. Learn more
Chris Galvan
Senior Manager of Cybersecurity & IR | Offensive Security | Cloud Security
View contribution
16
Stefano L.
Azure Engineer and Cyber Security Specialist @ Tactuum BSc in Cyber
Security
View contribution
12
Lazar V.
Senior Offensive Security Engineer @ UN1QUELY | OSCP
View contribution
12
See what others are saying
1Define the objectives
Before you start hacking, you need to know what you are
trying to achieve and how you will measure your success.
The objectives of a web app pentest project should be
aligned with the business goals, risk appetite, and
compliance requirements of the client or stakeholder. For
example, you may want to identify and prioritize the most
critical vulnerabilities, test the security controls and
defenses, or simulate a real-world attack scenario. You
should also agree on the scope, timeline, budget, and
deliverables of the project with the client or stakeholder.
Gather information
The next step is to gather as much information as possible
about the target web application and its environment. This
includes the domain name, IP address, hosting provider,
web server, framework, technology stack, functionality,
features, user roles, and data flows. You can use various
tools and techniques to perform passive and active
reconnaissance, such as DNS queries, web searches,
network scans, directory enumeration, banner grabbing,
spidering, and fingerprinting. The information you collect
will help you map the attack surface and plan your testing
strategy.
Choose the tools and methods
Once you have a clear picture of the target web application
and its environment, you need to choose the tools and
methods that suit your objectives and scope. There are
many tools and frameworks available for web app
pentesting, such as Nmap, Burp Suite, OWASP ZAP,
Metasploit, SQLmap, and Nikto. You should also familiarize
yourself with the common web application vulnerabilities
and attack vectors, such as the OWASP Top 10, SQL
injection, cross-site scripting, broken authentication, and
session hijacking. You should also decide whether you will
use automated or manual testing, or a combination of both,
and how you will document and report your findings.
1. All
2. Penetration Testing
How do you scope
and plan a web app
pentest project?
Powered by AI and the LinkedIn community
Define the objectives
Gather information
Choose the tools and methods
Perform the testing
Analyze and report
Here’s what else to consider
Top experts in this article
Selected by the community from 56 contributions. Learn more
Chris Galvan
Senior Manager of Cybersecurity & IR | Offensive Security | Cloud Security
View contribution
16
Stefano L.
Azure Engineer and Cyber Security Specialist @ Tactuum BSc in Cyber
Security
View contribution
12
Lazar V.
Senior Offensive Security Engineer @ UN1QUELY | OSCP
View contribution
12
See what others are saying
1Define the objectives
Before you start hacking, you need to know what you are
trying to achieve and how you will measure your success.
The objectives of a web app pentest project should be
aligned with the business goals, risk appetite, and
compliance requirements of the client or stakeholder. For
example, you may want to identify and prioritize the most
critical vulnerabilities, test the security controls and
defenses, or simulate a real-world attack scenario. You
should also agree on the scope, timeline, budget, and
deliverables of the project with the client or stakeholder.
Stefano L.
Follow
Azure Engineer and Cyber Security Specialist @ Tactuum BSc in
Cyber Security
In my experience when doing a web app pentest, it's
necessary to follow a well-defined methodology and
testing technique. This ensures that all portions of the
application are tested and no important vulnerabilities
are missed. Maintaining open communication and
engagement with the client or stakeholder throughout
the project ensures they are aware of any potential
risks or weaknesses and can reduce them.
Documenting the testing process, findings, and
recommendations helps clients and stakeholders
understand the results and improve the application's
security. Finally, web app pentesting requires a
constant improvement mindset. To keep the
application secure against new threats, it must be
retested and reassessed.
…see more
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12
Nathaniel Shere
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Penetration Testing, Cybersecurity Consulting | Making the Internet
safer one website at a time | DM me for security questions or
inquiries
Two key elements of defining objective scope for web
app pentests are which domains will be tested and
which user roles will be tested. For domains,
applications often link to or interact with other
domains and subdomains for functionality or data,
such as an auth.example.com for authentication or
api.example.com for data. For user roles, modern
applications often define many different roles, often
with nearly infinite permutations when roles are
defined by granular permissions instead of overall
definitions. In theory, every role would be tested for
access control issues but doing so can easily be
prohibitively expensive.
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Geraldo Alcantara, CISSP, CCISO, CCSK
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Pentester | Cybersecurity | CISSP | CCISO | CEH Master | CCSK |
CASP+ | Pentest+ | eWPTX | CRTP | eCPPT | eMAPT | eWPT | DCPT |
Security+ | 34x CVEs | MBA | LPIC-1 | AZ-900 | ISFS | EHF
Defining objectives is important because it sets the
direction and purpose of the web app pentest project.
It clarifies what needs to be achieved, such as
identifying vulnerabilities, assessing security controls,
or validating compliance requirements. Clear
objectives help focus the testing efforts, ensuring that
resources are allocated efficiently and that the desired
outcomes are achieved. Additionally, well-defined
objectives provide a basis for measuring the success
of the pentest and communicating its value to
stakeholders.
…see more
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YOGESWARAN M
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Cyber Security Engineer @ Finstein VAPT || Networking || System
Safety || SOC Elastic & Wazuh || Penetration Tester || AWS EC2 & S3
|| Bug Bounty Hunter || Security Researcher HOF 25+
Before diving in, clarify what you aim to achieve with
the pentest. Align your objectives with the business
goals, risk appetite, and compliance requirements of
your client or stakeholder. For instance, you might
want to identify critical vulnerabilities, assess security
controls, or simulate a real-world attack. Also, ensure
to agree on the scope, timeline, budget, and
deliverables to set clear expectations.
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Chris Galvan
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Senior Manager of Cybersecurity & IR | Offensive Security | Cloud
Security
In my experience, a penetration test should be treated
as a normal IT project in order to not fall into the
common pitfall of scope creep which I'm sure we've all
faced due to our love to hack thoroughly. This means
that there should be an experienced leader in the
team who has set out the teams objectives, priorities,
and KPI's for the year so they can manage the yearly
requests sent to pentest team. Having an intake
request form can help both parties have clear
expectations on: -Request priority -Date requesting
team needs the pentest report by -Type of pentest:
Web App, Cloud, Network, Endpoint Control Testing,
API Focused, or CI/CD(Few examples) -Key POC's -
Assets in scope -Times to test -Update expectations -
Credentials required
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2Gather information
The next step is to gather as much information as possible
about the target web application and its environment. This
includes the domain name, IP address, hosting provider,
web server, framework, technology stack, functionality,
features, user roles, and data flows. You can use various
tools and techniques to perform passive and active
reconnaissance, such as DNS queries, web searches,
network scans, directory enumeration, banner grabbing,
spidering, and fingerprinting. The information you collect
will help you map the attack surface and plan your testing
strategy.
Chris Galvan
Follow
Senior Manager of Cybersecurity & IR | Offensive Security | Cloud
Security
My best recommendation on gathering information is
for the penetration tester to create their own
methodology. There are plenty of checklists on GitHub
yet learning and building one from what you've done
will help you build confidence in teaching others.
Looking at the entire external or internal attack
surface is the best way to gather information from a
webapp. Personally I like to use plugins on Firefox
such as Shodan, Wappalyzer, and BuiltWith so I can
enumerate what ports are open, JS libraries, CDNs, 3rd
party Plugins, and tech stack. For public enumeration
the two tools that can be used by defenders and offsec
professionals are urlscan.io, dnsdumpster.com, and
using Google dorks on the site.
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16
Stefano L.
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Azure Engineer and Cyber Security Specialist @ Tactuum BSc in
Cyber Security
(edited)
In my experience, by gathering as much information
as possible about the target web application and its
environment, the penetration tester can gain a better
understanding of potential vulnerabilities and attack
vectors that could be exploited.
Like
5
Shahriar Khan
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Penetration Tester | Red Teamer | CRTO | HTB Top 10, Cybernetics,
Offshore, Dante
Collect as much information as possible about the web
application. This includes understanding its
architecture, functionality, and the technologies used.
This phase, often referred to as reconnaissance, helps
in planning the test effectively.
Like
5
YOGESWARAN M
Follow
Cyber Security Engineer @ Finstein VAPT || Networking || System
Safety || SOC Elastic & Wazuh || Penetration Tester || AWS EC2 & S3
|| Bug Bounty Hunter || Security Researcher HOF 25+
Next, collect comprehensive information about the
target web application and its environment. This
should include details like the domain name, IP
address, hosting provider, web server, technology
stack, and user roles. Utilize tools and techniques for
passive and active reconnaissance, such as DNS
queries, web searches, network scans, and directory
enumeration. The insights gained will help you map
the attack surface and refine your testing strategy.
…see more
Like
5
Nathaniel Shere
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Penetration Testing, Cybersecurity Consulting | Making the Internet
safer one website at a time | DM me for security questions or
inquiries
An excellent example of the value of information
gathering is performing reverse DNS lookups on the
target IP address or enumerating other domains that
resolve to the same IP address. These additional
domains are additional ways to access the same host
and environment and might even provide higher levels
of access, such as an admin portal that manages the
application but the code for which is hosted at a
different domain. Information like this may not directly
tie to active testing, depending on the defined scope,
but will provide valuable context for any identified
issues and can be eye opening for clients who didn’t
expect you to find it.
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3Choose the tools and methods
Once you have a clear picture of the target web application
and its environment, you need to choose the tools and
methods that suit your objectives and scope. There are
many tools and frameworks available for web app
pentesting, such as Nmap, Burp Suite, OWASP ZAP,
Metasploit, SQLmap, and Nikto. You should also familiarize
yourself with the common web application vulnerabilities
and attack vectors, such as the OWASP Top 10, SQL
injection, cross-site scripting, broken authentication, and
session hijacking. You should also decide whether you will
use automated or manual testing, or a combination of both,
and how you will document and report your findings.
Chris Galvan
Follow
Senior Manager of Cybersecurity & IR | Offensive Security | Cloud
Security
I agree with the tools mentioned above yet something
I learned after several months of pentesting is that it's
better to know how these tools work under the hood.
For example learning the default scan types and
enumerations kicked off will allow you to understand
how much traffic you're generating on the network or
against the load balancer. After understanding the
manual way of how these great tools work, it will allow
you to determine if there are limitations or payloads to
be mindful of. Automation is great once a foundation
has been built.
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8
Iain White
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Tech Consultant | IT Leader | Mentor | Virtual CTO | Leadership
Coach | Project Manager | Scrum Master | IT Strategy | Digital
Transformation | IT Governance | Agile | Lean | Theory Of
Constraints | SaaS | Brisbane.
Choosing the right tools and methods for a web app
pentest is pivotal. From my experience, blending both
manual insights and automated tools like Burp Suite
and OWASP ZAP yields the most comprehensive
understanding of vulnerabilities. It's not just about
identifying common vulnerabilities like SQL injection or
XSS but understanding the unique context of the
application. Automated tools can quickly cover
ground, but manual testing is crucial for nuanced
threats. Equally important is the documentation and
reporting phase, where findings must be
communicated effectively to drive remediation. This
approach not only uncovers critical vulnerabilities but
also fosters a culture of continuous security
improvement within the development lifecycle.
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Stefano L.
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Azure Engineer and Cyber Security Specialist @ Tactuum BSc in
Cyber Security
An example we can take is that Automated testing
tools can help increase efficiency by automating
repetitive tasks and performing scans on a large scale.
However, manual testing can provide a more thorough
and nuanced examination of the target system, and
can uncover vulnerabilities that automated tools might
miss. Therefore, it is often recommended to use a
combination of both automated and manual testing.
Finally, it is important to properly document and
report the findings of the penetration test. This
includes detailing the testing methodology, identifying
vulnerabilities, and providing recommendations for
remediation.
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Nathaniel Shere
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Penetration Testing, Cybersecurity Consulting | Making the Internet
safer one website at a time | DM me for security questions or
inquiries
Solely automated testing isn’t a penetration test. It is
a vulnerability scan at best. Generally, tools and
scripts serve a specific purpose within a larger testing
process. So, you might use Burp Suite for most of your
testing but use Nikto for information gathering and sql
map for exploiting any sql injection found.
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YOGESWARAN M
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Cyber Security Engineer @ Finstein VAPT || Networking || System
Safety || SOC Elastic & Wazuh || Penetration Tester || AWS EC2 & S3
|| Bug Bounty Hunter || Security Researcher HOF 25+
With a clear understanding of the target application,
select the tools and methods that best align with your
objectives. Options include Nmap, Burp Suite, OWASP
ZAP, Metasploit, and more. Familiarize yourself with
common web vulnerabilities, particularly those listed
in the OWASP Top 10. Decide on your approach—
whether automated, manual, or a combination—and
plan how you will document and report your findings.
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4Perform the testing
The testing phase is where you actually try to exploit the
vulnerabilities and weaknesses you identified in the
previous steps. You should follow a systematic and ethical
approach, respecting the scope, rules of engagement, and
legal boundaries of the project. You should also use a proxy
tool to intercept and manipulate the web requests and
responses, and a VPN or Tor to hide your identity and
location. You should also verify and validate your results,
and avoid causing any damage or disruption to the target
web application or its users.
5Analyze and report
The final step is to analyze and report your findings and
recommendations. You should organize and prioritize your
findings according to the severity, impact, and likelihood of
the vulnerabilities. You should also provide evidence and
screenshots to support your claims, and suggest
remediation steps and best practices to fix or mitigate the
vulnerabilities. You should also write a clear, concise, and
professional report that summarizes your objectives, scope,
methodology, results, and recommendations. You should
also communicate your report to the client or stakeholder
in a timely and respectful manner.
