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 * Jr Penetration Tester
 * Introduction to Pentesting
 * Pentesting Fundamentals


PENTESTING FUNDAMENTALS

Learn the important ethics and methodologies behind every pentest.

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Task 1What is Penetration Testing?




Before teaching you the technical hands-on aspects of ethical hacking, you'll
need to understand more about what a penetration tester's job responsibilities
are and what processes are followed in performing pentests (finding
vulnerabilities in a clients application or system).



The importance and relevancy of cybersecurity are ever-increasing and can be in
every walk of life. News headlines fill our screens, reporting yet another hack
or data leak.





Cybersecurity is relevant to all people in the modern world, including a strong
password policy to protect your emails or to businesses and other organisations
needing to protect both devices and data from damages.





A Penetration test or pentest is an ethically-driven attempt to test and analyse
the security defences to protect these assets and pieces of information. A
penetration test involves using the same tools, techniques, and methodologies
that someone with malicious intent would use and is similar to an audit.







According to Security Magazine, a cybersecurity industry magazine, there are
over 2,200 cyber attacks every day - 1 attack every 39 seconds.

Answer the questions below
Read me!
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Task 2Penetration Testing Ethics

The battle of legality and ethics in cybersecurity, let alone penetration
testing is always controversial. Labels like "hacking" and "hacker" often hold
negative connotations, especially in pop culture, thanks to a few bad apples.
The idea of legally gaining access to a computer system is a challenging concept
to grasp -- after all, what makes it legal exactly?



Recall that a penetration test is an authorised audit of a computer system's
security and defences as agreed by the owners of the systems. The legality of
penetration is pretty clear-cut in this sense; anything that falls outside of
this agreement is deemed unauthorised.


Before a penetration test starts, a formal discussion occurs between the
penetration tester and the system owner. Various tools, techniques, and systems
to be tested are agreed on. This discussion forms the scope of the penetration
testing agreement and will determine the course the penetration test takes.




Companies that provide penetration testing services are held against legal
frameworks and industry accreditation. For example, the National Cyber  
Security Centre (NCSC) has the CHECK accreditation scheme in the UK. This check
means that only "[CHECK]  approved companies can conduct authorised penetration
tests of public sector and CNI systems and networks." (NCSC).  


Ethics is the moral debate between right and wrong; where an action may be
legal, it may go against an individual's belief system of right and wrong.


Penetration testers will often be faced with potentially morally questionable
decisions during a penetration test. For example, they are gaining access to a
database and being presented with potentially sensitive data. Or they are,
perhaps, performing a phishing attack on an employee to test an organisation's
human security. If that action has been agreed upon during the initial stages,
it is legal -- however ethically questionable.


Hackers are sorted into three hats, where their ethics and motivations behind
their actions determine what hat category they are placed into. Let's cover
these three in the table below:



Hat CategoryDescriptionExampleWhite HatThese hackers are considered the "good
people". They remain within the law and use their skills to benefit others.For
example, a penetration tester performing an authorised engagement on a
company.Grey HatThese people use their skills to benefit others often; however,
they do not respect/follow the law or ethical standards at all times.For
example, someone taking down a scamming site.Black HatThese people  are
criminals and often seek to damage organisations or gain some form of financial
benefit at the cost of others. For example, ransomware authors infect devices
with malicious code and hold data for ransom.


Rules of Engagement (ROE)



The ROE is a document that is created at the initial stages of a penetration
testing engagement. This document consists of three main sections (explained in
the table below), which are ultimately responsible for deciding how the
engagement is carried out. The SANS institute has a great example of this
document which you can view online here.




SectionDescriptionPermissionThis section of the document gives explicit
permission for the engagement to be carried out. This permission is essential to
legally protect individuals and organisations for the activities they carry
out.Test ScopeThis section of the document will annotate specific targets to
which the engagement should apply. For example, the penetration test may only
apply to certain servers or applications but not the entire network.RulesThe
rules section will define exactly the techniques that are permitted during the
engagement. For example, the rules may specifically state that techniques such
as phishing attacks are prohibited, but MITM (Man-in-the-Middle) attacks are
okay.

Answer the questions below
You are given permission to perform a security audit on an organisation; what
type of hacker would you be?
Login to answer..Hint

You attack an organisation and steal their data, what type of hacker would you
be?

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What document defines how a penetration testing engagement should be carried
out?

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Task 3Penetration Testing Methodologies


Penetration tests can have a wide variety of objectives and targets within
scope. Because of this, no penetration test is the same, and there are no
one-case fits all as to how a penetration tester should approach it. 

The steps a penetration tester takes during an engagement is known as the
methodology. A practical methodology is a smart one, where the steps taken are
relevant to the situation at hand. For example, having a methodology that you
would use to test the security of a web application is not practical when you
have to test the security of a network.




Before discussing some different industry-standard methodologies, we should note
that all of them have a general theme of the following stages:





StageDescriptionInformation Gathering

This stage involves collecting as much publically accessible information about a
target/organisation as possible, for example, OSINT and research.

Note: This does not involve scanning any systems.

Enumeration/ScanningThis stage involves discovering applications and services
running on the systems. For example, finding a web server that may be
potentially vulnerable.ExploitationThis stage involves leveraging
vulnerabilities discovered on a system or application. This stage can involve
the use of public exploits or exploiting application logic.Privilege
EscalationOnce you have successfully exploited a system or application (known as
a foothold), this stage is the attempt to expand your access to a system. You
can escalate horizontally and vertically, where horizontally is accessing
another account of the same permission group (i.e. another user), whereas
vertically is that of another permission group (i.e. an
administrator).Post-exploitation

This stage involves a few sub-stages:


1. What other hosts can be targeted (pivoting)

2. What additional information can we gather from the host now that we are a
privileged user

3.  Covering your tracks

4. Reporting







OSSTMM






The Open Source Security Testing Methodology Manual provides a detailed
framework of testing strategies for systems, software, applications,
communications and the human aspect of cybersecurity.




The methodology focuses primarily on how these systems, applications
communicate, so it includes a methodology for:

 1. Telecommunications (phones, VoIP, etc.)
 2. Wired Networks
 3. Wireless communications

AdvantagesDisadvantagesCovers various testing strategies in-depth.
The framework is difficult to understand, very detailed, and tends to use unique
definitions.
Includes testing strategies for specific targets (I.e. telecommunications and
networking) 
Intentionally left blank.The framework is flexible depending upon the
organisation's needs.
Intentionally left blank.
The framework is meant to set a standard for systems and applications, meaning
that a universal methodology can be used in a penetration testing scenario.
Intentionally left blank.




OWASP






The "Open Web Application Security Project" framework is a community-driven and
frequently updated framework used solely to test the security of web
applications and services.




The foundation regularly writes reports stating the top ten security
vulnerabilities a web application may have, the testing approach, and
remediation.




AdvantagesDisadvantagesEasy to pick up and understand.It may not be clear what
type of vulnerability a web application has (they can often overlap).
Actively maintained and is frequently updated.
OWASP does not make suggestions to any specific software development life
cycles.
It covers all stages of an engagement: from testing to reporting and
remediation.
The framework doesn't hold any accreditation such as CHECK.
Specialises in web applications and services.
Intentionally left blank.






NIST Cybersecurity Framework 1.1






The NIST Cybersecurity Framework is a popular framework used to improve an
organisations cybersecurity standards and manage the risk of cyber threats. This
framework is a bit of an honourable mention because of its popularity and
detail.




The framework provides guidelines on security controls & benchmarks for success
for organisations from critical infrastructure (power plants, etc.) all through
to commercial.  There is a limited section on a standard guideline for the
methodology a penetration tester should take.







AdvantagesDisadvantagesThe NIST Framework is estimated to be used by 50% of
American organisations by 2020.
NIST has many iterations of frameworks, so it may be difficult to decide which
one applies to your organisation.
The framework is extremely detailed in setting standards to help organisations
mitigate the threat posed by cyber threats.
The NIST framework has weak auditing policies, making it difficult to determine
how a breach occurred.
The framework is very frequently updated.
The framework does not consider cloud computing, which is quickly becoming
increasingly popular for organisations.
NIST provides accreditation for organisations that use this framework.
Intentionally left blank.
The NIST framework is designed to be implemented alongside other frameworks.
Intentionally left blank.





NCSC CAF






The Cyber Assessment Framework (CAF) is an extensive framework of fourteen
principles used to assess the risk of various cyber threats and an
organisation's defences against these.




The framework applies to organisations considered to perform "vitally important
services and activities" such as critical infrastructure, banking, and the
likes. The framework mainly focuses on and assesses the following topics:

 * Data security
 * System security
 * Identity and access control
 * Resiliency
 * Monitoring
 * Response and recovery planning




AdvantagesDisadvantagesThis framework is backed by a government cybersecurity
agency.
The framework is still new in the industry, meaning that organisations haven't
had much time to make the necessary changes to be suitable for it.
This framework provides accreditation.
The framework is based on principles and ideas and isn't as direct as having
rules like some other frameworks.
This framework covers fourteen principles which range from security to response.
Intentionally left blank.


Answer the questions below
What stage of penetration testing involves using publicly available information?
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If you wanted to use a framework for pentesting telecommunications, what
framework would you use? Note: We're looking for the acronym here and not the
full name.


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What framework focuses on the testing of web applications?

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Task 4Black box, White box, Grey box Penetration Testing


There are three primary scopes when testing an application or service. Your
understanding of your target will determine the level of testing that you
perform in your penetration testing engagement. In this task, we'll cover these
three different scopes of testing.




Black-Box Testing

This testing process is a high-level process where the tester is not given any
information about the inner workings of the application or service.

The tester acts as a regular user testing the functionality and interaction of
the application or piece of software. This testing can involve interacting with
the interface, i.e. buttons, and testing to see whether the intended result is
returned. No knowledge of programming or understanding of the programme is
necessary for this type of testing.

Black-Box testing significantly increases the amount of time spent during the
information gathering and enumeration phase to understand the attack surface of
the target.





Grey-Box Testing

This testing process is the most popular for things such as penetration testing.
It is a combination of both black-box and white-box testing processes.The tester
will have some limited knowledge of the internal components of the application
or piece of software. Still, it will be interacting with the application as if
it were a black-box scenario and then using their knowledge of the application
to try and resolve issues as they find them.

With Grey-Box testing, the limited knowledge given saves time, and is often
chosen for extremely well-hardened attack surfaces.










White-Box Testing

This testing process is a low-level process usually done by a software developer
who knows programming and application logic. The tester will be testing the
internal components of the application or piece of software and, for example,
ensuring that specific functions work correctly and within a reasonable amount
of time.

The tester will have full knowledge of the application and its expected
behaviour and is much more time consuming than black-box testing. The full
knowledge in a White-Box testing scenario provides a testing approach that
guarantees the entire attack surface can be validated.

Answer the questions below
You are asked to test an application but are not given access to its source code
- what testing process is this?
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You are asked to test a website, and you are given access to the source code -
what testing process is this?

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Task 5Practical: ACME Penetration Test
Task includes website
View Site
ACME has approached you for an assignment. They want you to carry out the stages
of a penetration test on their infrastructure. View the site (by clicking the
green button on this task) and follow the guided instructions to complete this
exercise.
Answer the questions below
Complete the penetration test engagement against ACME's infrastructure.
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