What Are The Different Types of Penetration Testing Purplesec

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2021 Trends Report Breach Report Learn

2021 Trends Report Breach Report Learn
05
Oct
What Are The Di�erent Types Of

Penetration Testing?
 By Jason Firch, MBA |  Reviewed By Michael Swanagan, CISSP, CISA, CISM |
 In Penetration Testing |  Comments
Penetration testing attempts to exploit weaknesses or vulnerabilities in systems,

networks, human resources, or physical assets in order to stress test the
1 of 26 21-09-2021, 13:36
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e�ectiveness of security controls.

What Are The Di�erent Types Of 2021 Trends Report Breach Report Learn
Penetration
The di�erentTesting?
types of penetration tests include network services, applications,
client side, wireless, social engineering, and physical. A penetration test may be
performed externally or internally to simulate di�erent attack vectors.
Depending on the goals of each test, a penetration tester may or may not have
Security Categories
prior knowledge of the environment and systems they’re attempting to breach.
Cyber
This Security (20) as black box, white box, and gray box penetration testing.
is categorized
Managed Security (6)
Network Vulnerabilities (9)
Penetration Testing (11)
Recent Cyber Attacks (4)
Social Engineering (5)
2 of 26 21-09-2021, 13:36
Wireless Network Social Engineering

Security Categories
Physical
Cyber Security (20) Firewall Web Application

In this article, I’m going to explain the di�erent types of penetration tests, how they
work, and Vulnerabilities
Network why they should (9) be performed. By the end, you will have a better
understanding of why penetration tests are an e�ective layer of defense for any
successful cyber security program.

Before we dive into the di�erent types of penetration testing let’s �rst de�ne what a
penetration test is.
Article Navigation
3 of 26 21-09-2021, 13:36
• What Is A Penetration Test?

What
• WhatAre ThePrimary
Is The Di�erent Types
Purpose OfOf
Penetration2021
Testing?
Trends Report Breach Report Learn
Penetration
• Testing?
What Are The Di�erent Approaches To Penetration Testing?
◦ Black Box
◦ White Box
◦ Gray Box
Security
• Types CategoriesTesting
Of Penetration
◦ Network Services
Cyber Security (20)
◦ Web Application
◦ Client-Side
◦ Wireless
◦ Social Engineering
◦ Physical Penetration Testing

What Is A Penetration Test?


A penetration test involves a team of security professionals who actively attempt to
break into your company’s network by exploiting weaknesses and vulnerabilities in
your systems.
4 of 26 21-09-2021, 13:36
Penetration tests may include any of the following methods:

Security Categories
• Using social engineering techniques to access systems and related databases.

Cyber Security (20)
• Sending of phishing emails to access critical accounts.
Managed
• Using Security (6)
unencrypted passwords shared in the network to access sensitive databases.

These attempts can be far more intrusive than a vulnerability scan and may cause a
denial of service
Penetration or (11)
Testing increased system utilization, which may reduce productivity,
and corrupt the machines.
InSocial
someEngineering
cases, you(5)
may schedule penetration tests and inform sta� in advance of
the exercise. However, this wouldn’t be applicable if you want to test how your
internal security team responds to a “live” threat.
For example, red team exercises are often performed without informing sta� to test
real-world threat scenarios.
In this case, it’s important to inform the blue team lead, CISO, or upper-level
management of the exercise. This ensures the response scenario is still tested, but
with tighter control when/if the situation is escalated.
Regardless of the scenario you should conduct a penetration test with a speci�c
intent and clearly de�ne your wants and needs with the penetration testing team.
5 of 26 21-09-2021, 13:36
What Are Theyou

For example, Di�erent Types
may just Ofrolling out
�nish 2021 Trends
a new Report program
security Breach
forReport
your Learn
Penetration
business andTesting?
want to test its e�ectiveness.
A penetration test can determine if certain objectives of the program have been
achieved such as maintaining 99.99% availability during an attack, or ensuring data
Security Categories
loss prevention (DLP) systems are blocking would-be attackers from ex�ltrating
Cyber Security (20)
data.

Read More: 10 Cyber Security Trends You Can’t Ignore In 2021
What IsTesting
Penetration The(11)Primary Purpose Of Penetration
Testing?
Penetration testing(5)
Social Engineering has become a widely adopted security practice by
organizations in recent years.
This is especially true for industries, such as banks or healthcare providers, that
store and access sensitive or private information.
While the primary purpose is to expose vulnerabilities or exploit weaknesses, it’s

important to note that the main goal of a pen test is often tied to a business
objective with an overarching strategy.
For example, Department of Defense contractors must have adequate processes in

place to protect Controlled Unclassi�ed Information (CUI) as part of the Cyber
Security Maturity Certi�cation (CMMC).
6 of 26 21-09-2021, 13:36
What Are The test

A penetration Di�erent
is oneTypes Of security
of many 2021 Trendsneeded
controls Report to pass
Breach Report
auditor Learn
Penetration
requirementsTesting?
depending on the level that the contractor must attain.
On the other hand, a software company’s security goals may vary greatly.
Security Categories
For example, application penetration testing helps to identify �aws and
Cyber Security
weaknesses (20) code that could be susceptible to an attack. Developers then
within
work to create �xes to update the codebase.
Network Vulnerabilities
Ultimately, the business(9)goals determine the types of penetration testing
performed, which we will cover shortly.
Reporting
Recent CyberOn Findings
Attacks (4)

Upon completion of the testing phase, a report is created and presented to
executive leadership and business owners. This is the real value of any penetration
testing engagement.
This report should provide direction and guidance for reducing exposure to risk
while also providing actionable steps towards a resolution.
It’s important to mention that penetration testing reports are customize tailored to
meet a company’s cyber security needs based on:
• How their network is set up.
• Business objectives for performing a pen test.
7 of 26 21-09-2021, 13:36
• What is being tested – software, servers, endpoints, physical controls, etc.

What
• Are The
The value Di�erent
of tangible Types Of assets being
or intangible 2021secured.
Trends Report Breach Report Learn
Penetration
• Testing?
And much more!
Security Categories
Cyber Security (20)
When consulting with vendors, be sure to ask how they plan to present their
�ndings. The last thing you want is to pay a company $30,000 for a PDF document
with no explanation.
8 of 26 21-09-2021, 13:36
What Are The we

At PurpleSec, Di�erent TypestoOf
tell clients set aside 2021 Trends
at least Report
1 hour with ourBreach Report
technical team, Learn
encourage them to ask questions, and to challenge our �ndings. As a result, they
clearly understand every aspect of the report, their risk rating, and the pathway to
remediating their exposure.
Security Categories
Security Policy Templates
Cyber Security (20)
Information Technology (IT) is an integral and critical component of daily business.
This policy seeks to ensure that IT resources e�ciently serve the primary business
functions, provide security for members’ electronic data, and comply with federal
and other regulations.
What Are The Di�erent Approaches To

Penetration tests di�er both in their approach and in the weaknesses they attempt
to exploit. The level of information provided to the pen tester will determine their
approach as well as the scope of the project.
9 of 26 21-09-2021, 13:36
What Are Thewill

For example, Di�erent Types Of tester have
the penetration 2021 Trends Reportof how
knowledge Breach Reportis
a network Learn
mapped, or are they required to uncover this information on their own?
The di�erent approaches to penetration testing include:
Security Categories
• Black Box
Cyber Security
• White Box (20)
• Gray Box
Black Box
Network Penetration
Vulnerabilities (9) Testing
Penetration
During Testing
a black (11)
box penetration test (also known as external penetration testing) the
pen tester is given little to no information regarding the IT infrastructure of a
business.
The main bene�t of this method of testing is to simulate a real-world cyber attack,
whereby the pen tester assumes the role of an uninformed attacker.
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A black box penetration test can take up to six weeks to complete making it one of
the longestCategories
Security types of penetration tests. Businesses can expect to pay between
$10,000 – $25,000 due to the level of e�ort involved in planning, performing,
Cyber Security (20)
testing, and completing the report.

This, of course, all depends on the scope of the project.
One of the easiest

Penetration Testingways
(11) for pen testers to break into a system during a black box
test is by deploying a series of exploits known to work, such as Kerberoasting.
This method of testing is also referred to as the “trial and error” approach, however,
there is a high degree of technical skill involved in this process.
White Box Penetration Testing
White box penetration testing (also called clear box testing, glass box testing, or
internal penetration testing) is when the pen tester has full knowledge and access
to the source code and environment.
The goal of a white box penetration test is to conduct an in-depth security audit of
a business’s systems and to provide the pen tester with as much detail as possible.
As a result, the tests are more thorough because the pen tester has access to areas
11 of 26 21-09-2021, 13:36
where a black box test cannot, such as quality of code and application design.
Security Categories
Cyber Security (20)

White box tests do have their disadvantages. For instance, given the level of access
the pen tester has it can take longer to decide what areas to focus on. In addition,
this method of testing often requires sophisticated and expensive tools such as
code analyzers and debuggers.
White box tests can take two to three weeks to complete and cost between $4,000
– $20,000.
In the end, it doesn’t matter whether you perform a black box or a white box
penetration test so long as the primary goal of the test is being met.
Gray Box Penetration Testing
12 of 26 21-09-2021, 13:36
What
DuringAre The box
a gray Di�erent Types Of
penetration 2021
test, the pen Trends
tester Report
has Breach Report
partial knowledge or accessLearn
Penetration
to an internalTesting?
network or web application.
A pen tester may begin with user privileges on a host and be told to escalate their
privileges to a domain admin. Or, they could be asked to get access to software
Security Categories
code and system architecture diagrams.
Cyber Security (20)
One main advantage of a gray box penetration test is that the reporting provides a
more focused and e�cient assessment of your network’s security.
For instance, instead of spending time with the “trial and error” approach, pen
testers performing a gray box penetration test are able to review the network
diagrams to identify areas of greatest risk.
13 of 26 21-09-2021, 13:36
What Are The

From there, theDi�erent Types Of
proper countermeasures2021
can Trends Report
be recommendedBreach Report
to �ll the gaps. Learn
Types Of Penetration Testing
The di�erent
Security types of penetration testing include:
Categories
Cyber Security
• Network (20)
Services
• Web Application
• Client Side
• Wireless
• Social Engineering
• Physical Penetration Testing

Each type of penetration test requires speci�c knowledge, methodologies, and
tools to perform and should align with a speci�c business goal.
These goals could range from improving awareness of social engineering attacks to
employees company-wide, to implementing secure code development to identify
�aws in software code in real-time, or meeting regulatory or compliance
obligations.
Network Service Penetration Testing
Network service penetration testing, or infrastructure testing, is one of the most

common types of penetration testing performed.
14 of 26 21-09-2021, 13:36
Security Categories
Cyber Security (20)
Network
The main Vulnerabilities
purpose is to (9)
identify the most exposed vulnerabilities and security
weaknesses in the network infrastructure (servers, �rewalls, switches, routers,
printers, workstations, and more) of an organization before they can be exploited.
Why Should You Perform A Network Service Penetration Test?

Network penetration tests should be performed to protect your business from

common network-based attacks including:
• Firewall Miscon�guration And Firewall Bypass
• IPS/IDS Evasion Attacks
• Router Attacks
• DNS Level Attacks:
◦ Zone Transfer Attacks
◦ Switching Or Routing Based Attacks
• SSH Attacks
• Proxy Server Attacks
• Unnecessary Open Ports Attacks
15 of 26 21-09-2021, 13:36
• Database Attacks
What
• Man Are The
In The Di�erent
Middle Types
(MITM) Of
Attacks 2021 Trends Report Breach Report Learn
Penetration
• Testing?
FTP/SMTP Based Attacks
Given that a network provides mission-critical services to a business, it is

recommended that both internal and external network penetration tests be
Security Categories
performed at least annually. This will provide your business with adequate
coverage to protect
Cyber Security (20) against these attack vectors.

Web Application Penetration Testing
Web application penetration testing is used to discover vulnerabilities or security
Penetration Testing
weaknesses (11)
in web-based applications. It uses di�erent penetration techniques and
attacks with aims to break into the web application itself.
16 of 26 21-09-2021, 13:36
What Are The

The typical Di�erent
scope Types
for a web Of
application 2021 Trends Report
penetration Breach
test includes webReport
based Learn
Penetration
applications,Testing?
browsers, and their components such as ActiveX, Plugins, Silverlight,
Scriptlets, and Applets.
These types of tests are far more detailed and targeted and therefore are
Security Categories
considered to be a more complex test. In order to complete a successful test, the
Cyber Security
endpoints (20) web-based application that interacts with the user on a regular
of every
basis must be identi�ed.
Network
This Vulnerabilities
requires (9) of e�ort and time from planning to executing the test,
a fair amount
and �nally compiling a useful report.
Recent
The Cyber Attacks
techniques of web(4)application penetration testing are continuously evolving
with time due to the increase in threats coming from web applications day by day.
This threat has expanded greatly since the outbreak of COVID-19, resulting a 600%
increase in cybercrime.
Why Should You Perform A Web Application Penetration Test?
A key reason to perform a web application penetration test is to identify security

weaknesses or vulnerabilities within the web based applications and its
components like Database, Source Code, and the back-end network.
It also helps by prioritizing the determined weaknesses or vulnerabilities and

provides possible solutions to mitigate them.
17 of 26 21-09-2021, 13:36
In software application development it’s considered best practice to continuously

What
improveArethe
The Di�erent Deploying
codebase. Types Of a secure2021 Trends
and agileReport Breach
code is the Report
phrase Learn
often used
to describe this practice.
Agile code deployment is the preferred method over large batch deployments, as
the more variables introduced into the code in a single deployment, the more
Security Categories
opportunities there are to create bugs or errors leading to security vulnerabilities.
Cyber Security (20)
As a result, technical debt forms, where developers gradually spend more time
implementing �xes to problems then they do develop new features or updates.
In contrast, agile methodologies use a sandbox environment (a duplicate copy of

the codebase) to test code functionality and usability prior to launching into
Recent Cyber
production. Attacks
If the (4)
deployment is unsuccessful, developers can easily single out the
change and roll the code back to previous version history.
The trick is balancing daily code deployment with security in mind.
It’s not uncommon for enterprise software companies to employ pen testers to
continuously test their code. Google, as well as other tech giants, o�er a reward for
�nding and reporting on vulnerabilities within their applications.
Client Side Penetration Testing
Client side penetration testing is used to discover vulnerabilities or security

weaknesses in client side applications.
18 of 26 21-09-2021, 13:36
These could be a program or applications such as Putty, email clients, web

What Are (i.e.
browsers TheChrome,
Di�erentFirefox,
Types Of 2021
Safari, etc.), Trends Report
Macromedia Breach
Flash, and Report
others. Learn
Programs
Penetration Testing? and the Microsoft O�ce Suite are also subject to testing.
like Adobe Photoshop
Why Should You Perform A Client-Side Penetration Test?
Security Categories
Client-side tests are performed to identify speci�c cyber attacks including:
Cyber Security (20)

• Cross-Site Scripting Attacks
• Clickjacking Attacks
• Cross-Origin Resource Sharing (CORS)

• Form Hijacking
Penetration
• HTML Testing (11)
Injection
• Open Redirection
• Malware Infection

Wireless Penetration Testing
Wireless penetration testing involves identifying and examining the connections

between all devices connected to the business’s wi�. These devices include
laptops, tablets, smartphones, and any other internet of things (IoT) devices.
19 of 26 21-09-2021, 13:36
Wireless penetration tests are typically performed onsite as the pen tester needs to
Security Categories
be in range of the wireless signal to access it. Alternatively, a NUC and WiFi
Pineapple can be deployed onsite to remotely perform the test.
Cyber Security (20)
Managed
Why Security
Should (6)
You Perform A Wireless Penetration Test?

Wireless communications are an invisibly running service that allows data to �ow in
and out of the
Penetration network.
Testing (11) Therefore, this wireless network must be secured from any
weaknesses like unauthorized access or data leakage.

Before
Socialperforming a wireless penetration test you should consider the following:
Engineering (5)
• Have all access points been identi�ed and how many use poor encryption methods?
• Is the data �owing in and out of the network encrypted and if so, how?
• Are there monitoring systems in place to identify unauthorized users?
• Is there any possibility the IT team could have miscon�gured or duplicated a wireless
network?
• What are the current measures in place to protect the wireless network?
• Are all wireless access points using WPA protocol?
Social Engineering Penetration Testing
Social engineering penetration testing is where a malicious actor attempts to
20 of 26 21-09-2021, 13:36
persuade or trick users into giving them sensitive information, such as a username
What Are The Di�erent Types Of
and password. 2021 Trends Report Breach Report Learn
Security Categories
Cyber Security (20)
Common types of social engineering attacks used by pen testers include:

• Phishing Attacks
• Vishing
• Smishing
• Tailgating
• Imposters (i.e. Fellow Employees, External Vendors, or Contractors)
• Name Dropping
• Pre-texting
• Dumpster Diving
• Eavesdropping
• Gifts
Why Should You Perform Social Engineering Tests?
21 of 26 21-09-2021, 13:36
What Are The

According Di�erent
to recent Types Of
statistics, 98% of all 2021
cyberTrends Report
attacks Breach
rely on social Report
engineering. Learn
This is because internal users are one of the biggest threats to a networks security
and due to how lucrative the scams are.
Social engineering tests and awareness programs have proven to be one of the
Security Categories
most e�ective methods of mitigating an attack.
Cyber Security (20)
For example, KnowBe4, the popular email phishing platform, simulates an email
phishing attack. When the user clicks on the link they’re taken to a page that
Network
informs Vulnerabilities
them that it was (9)a phishing test.
Remediation training is then provided to help educate and inform users on the most
current cyber attacks and how to avoid them.
Physical Penetration Testing
22 of 26 21-09-2021, 13:36
Physical penetration testing simulates a real-world threat whereby a pen tester

What Are to
attempts The Di�erent Types
compromise Of barriers
physical 2021 Trends Report
to access a business’sBreach Report
infrastructure, Learn
building, systems, or employees.
Security Categories
Cyber Security (20)

Why Should You Perform A Physical Penetration Test?
Physical barriers are often an afterthought for most businesses, however, if a

malicious actor is able to gain physical access to your server room then they could
own your network. Imagine the impact that might have on your business, on your
customers, as well as business partnerships.
The primary bene�t of a physical penetration test is to expose weaknesses and

vulnerabilities in physical controls (locks, barriers, cameras, or sensors) so that �aws
can be quickly addressed. Through identifying these weaknesses proper
mitigations can be put in place to strengthen the physical security posture.
23 of 26 21-09-2021, 13:36
Are you ready to work together? Get a no-obligation consultation to meet your
What Are The
penetration Di�erent
testing Types Of
needs. 2021 Trends Report Breach Report Learn
Related Articles
• Vulnerability Scans VS Penetration Tests: What’s The Main Di�erence?

Security Categories
• How Often Should You Perform A Penetration Test?
• How
CyberToSecurity
Perform(20)
A Successful Network Vulnerability Assessment
• How Often Should You Perform A Network Vulnerability Scan?

• What Are The Most Common Types Of Network Vulnerabilities?

Jason Firch, MBA
Penetration Testing (11) is a veteran IT operations manager, digital marketer, as well
Jason
as the co-founder and CEO of PurpleSec, with nearly a decade of
experience in business management and operations. When he's
Social Engineeringnot
(5) studying for his CISSP or contributing to the PurpleSec blog
you'll �nd Jason helping nonpro�ts with their online marketing.
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2021 Trends Report Breach Report Learn

What Are The Di�erent Types Of

Penetration testing attempts to exploit weaknesses or vulnerabilities in systems,

e�ectiveness of security controls.

Managed Security (6)

Network Vulnerabilities (9)

Penetration Testing (11)

Recent Cyber Attacks (4)

Social Engineering (5)

Wireless Network Social Engineering

Managed Security (6)

Recent Cyber Attacks (4)

• What Is A Penetration Test?

◦ Physical Penetration Testing

What Is A Penetration Test?

Social Engineering (5)

Penetration tests may include any of the following methods:

• Using social engineering techniques to access systems and related databases.

Network Vulnerabilities (9)

What Are Theyou

Managed Security (6)

While the primary purpose is to expose vulnerabilities or exploit weaknesses, it’s

For example, Department of Defense contractors must have adequate processes in

What Are The test

Social Engineering (5)

• How their network is set up.

• Business objectives for performing a pen test.

• What is being tested – software, servers, endpoints, physical controls, etc.

Cyber Security (20)

Managed Security (6)

Network Vulnerabilities (9)

Penetration Testing (11)

Recent Cyber Attacks (4)

Social Engineering (5)

What Are The we

Penetration Testing (11)

Recent Cyber Attacks (4)

Social Engineering (5)

What Are The Di�erent Approaches To

What Are Thewill

The di�erent approaches to penetration testing include:

Managed Security (6)

One of the easiest

White Box Penetration Testing

Cyber Security (20)

Managed Security (6)

Network Vulnerabilities (9)

Penetration Testing (11)

Recent Cyber Attacks (4)

Social Engineering (5)

Gray Box Penetration Testing

Managed Security (6)

Network Vulnerabilities (9)

Penetration Testing (11)

Recent Cyber Attacks (4)

Social Engineering (5)

What Are The

Types Of Penetration Testing

Recent Cyber Attacks (4)

Network Service Penetration Testing

Network service penetration testing, or infrastructure testing, is one of the most