Penetration Testing Facts
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Wilmington University *
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210
Subject
Information Systems
Date
Dec 6, 2023
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4
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11.1.2 Penetration Testing Facts
Penetration testing, also commonly referred to as pentesting or ethical hacking, is the
authorized simulation of an attack against an organization's security infrastructure. This can
include physical and network security.
This lesson covers the following topics:
Types of penetration tests
Security teams
Documentation/contracts
Penetration testing life cycle
Types of Penetration Tests
The purpose of a penetration test is to discover any vulnerability in an organization's network or
physical security. Di±erent types of penetration tests can be performed to simulate internal or
external threats. The following table details the types of penetration tests:
Penetration
Test Type
Description
White box
The ethical hacker is given full knowledge of the target or network. This test allows for a
comprehensive and thorough test, but is not very realistic.
Black box
The ethical hacker has no information regarding the target or network. This type of test
best simulates an outside attack and ignores insider threats.
Gray box
The ethical hacker is given partial information of the target or network, such as IP
con²gurations, email lists, etc. This test simulates the insider threat.
Bug bounties
These unique tests are programs that are setup by organizations such as Google,
Facebook, and many others.
The organization sets strict guidelines and boundaries for ethical hackers to operate
within. Any discovered vulnerabilities are reported and the ethical hacker is paid based
on the severity of the vulnerability.
Security Teams
Depending on their role, members of security operations can be placed on di±erent teams.
These teams all work together to discover and ²x security vulnerabilities.
The following table describes the more common security teams:
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Security
Team
Description
Red team
The red team members are the ethical hackers. This team is responsible for performing the
penetration tests.
Blue team
Blue team members are the defense of the system. This team is responsible for stopping the
red team's advances.
Purple
team
Members of the purple team work on both o±ense and defense. This team is a combination
of the red and blue teams.
White team
The white team members are the referees of cybersecurity. This team is responsible for
managing the engagement between the red and blue teams. This group typically consists of
the managers or team leads.
Documentation/Contracts
Before any penetration test can take place, the goals and guidelines of the test must be
established. These are spelled out in the scope of work and rules of engagement documents.
The following table describes these important documents:
Document
Type
Description
Scope of work
The scope of work is a very detailed document that de²nes exactly what is going to be
included in the penetration test. This document is also referred to as the statement of
work. This document should answer the:
Who - speci²c IP ranges, servers, applications, etc. should be explicitly listed.
What - anything that is o± limits, such as speci²c servers or tactics, should be
explicity listed.
When - the time frame for the penetration test. This should identify how long the
test will run, the deliverables, and when the deliverables are due.
Where - the location of the penetration tester. Sometimes the penetration tester
will be located in a di±erent state. In this case, all parties must agree on which
state laws will be followed.
Why - the purpose and goals of the test. Penetration tests are often performed
for compliance purposes and these requirements must be detailed in the
document.
Special considerations, such as travel, required certi²cations, or anything else unexpected
will be de²ned in the scope of work.
Finally, the scope of work should de²ne payment and how to handle requests for
additional work. This will help to reduce scope creep.
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Rules of
engagement
The rules of engagement document de²nes exactly how the penetration test will be
carried out. The following should be de²ned in the rules of engagement:
Type of test - whether the test will be a white box, black box, or gray box test.
Data handling - an explicit statement of how sensitive data is to be handled. Be
aware that the pentester will typically come across sensitive data during a
penetration test.
Noti²cations - the detailed process on when and how to notify the IT team.
Penetration Testing Life Cycle
Once the paperwork is complete, the pentester can begin work. The following table covers the
phases of the penetration testing life cycle.
Penetration Testing
Life Cycle Phase
Description
Perform
reconnaissance
The ²rst phase in the pentesting process is reconnaissance, also known as
footprinting. In this phase, the pentester begins gathering information on the
target. This can include gathering publicly available information, using social
engineering techniques, or even dumpster diving.
Scan/enumerate
Running scans on the target is the second phase. During this phase, the ethical
hacker is actively engaged with the target.
Enumeration is part of the scanning phase. Enumeration uses scanning techniques
to extract information such as:
Usernames
Computer names
Network resources
Share names
Running services
Gain access
The third phase takes all of the information gathered in the reconnaissance and
scanning phases to exploit any discovered vulnerabilities in order to gain access.
After gaining access, the pentester can perform lateral moves, pivoting to other
machines on the network. The pentester will begin trying to escalate privileges with
the goal of gaining administrator access.
Maintain Access
Once the pentester has gained access, maintaining that access becomes the next
priority. This can be done by installing backdoors, rootkits, or Trojans.
Report
The ²nal phase is generating the test results and supporting documentation. After
any penetration test, a detailed report must be compiled. Documentation provides
extremely important protection for both the penetration tester and the
organization.
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