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The Art of
Penetration Testing
Index
1. Purpose Of Penetration Testing
2. Types of Penetration Testing
3. 3 Different Approaches To Penetration Testing
4. Penetration Testing Methodologies
5. 8 Phases of Penetration Testing
6. Penetration Testing Tools
7. Challenges in Penetration Testing
8. Advantages Of Penetration Testing
9. Disadvantages Of Penetration Testing
10. Conclusion
Purpose Of Penetration Testing
• We find vulnerabilities before
hackers do.
• Identify weaknesses that
threaten the integrity of your web
resource or network by
undergoing the simulated attack.
• Prevent breaches and create a
robust security posture.
• Ensure the security of the data
and continuous workflow with
the help of experienced ethical
hackers.
4
1. Penetration testing is a crucial aspect
of modern cybersecurity, and it
involves identifying vulnerabilities in a
system by simulating an attack. There
are different types of penetration
testing, including network testing,
web application testing, and wireless
testing.
2. Network testing involves evaluating
the security of a network,
3. web application testing focuses on
finding vulnerabilities in web
applications.
4. Wireless testing is used to identify
weaknesses in wireless networks,
such as those used for Wi-Fi.
Types of Penetration Testing
5
White Box Penetration Testing
In a white box test, is also called as
Clear box and Transparent box testing,
Here the pen tester has a complete
knowledge and familiar to access all
the source code of the application and
software architecture.
Black Box Penetration Testing
As you have guessed correctly,
in black box penetration testing is also
called as real-world cyber attack. The
tester has no knowledge of the
system and designs of architecture
here the tester will use
6
the different techniques to break the system or infrastructure.
Gray Box Penetration Testing
In a Gray box test, it will blend together the White & Black box test, Here
the tester have a partial knowledge of understanding the infrastructure and
system, Those tester are only focus on those area of the system they most
understand
7
Penetration Testing Methodologies
• Penetration testing is a critical
component of ensuring the security of
digital systems. There are several
methodologies that can be employed
when conducting a penetration test,
including the Open-Source Security
Testing Methodology Manual
(OSSTMM) and the Penetration Testing
Execution Standard (PTES). These
methodologies provide a structured
approach to testing and help ensure
that all aspects of the system are
thoroughly evaluated.
8
• The OSSTMM(Open-Source Security Testing Methodology Manual), In
this methodology the pen tester will do the manual test, Here the IT
team & Security testing team Will work together.
• The PTES(Penetration Testing Execution Standard), this on other way
to do pen test , It provides a more comprehensive framework This
Metrology is used for automation pen test with the help of some Tools.
9
Penetration Testing Tools
• Metasploit is a powerful framework
that allows penetration testers to
automate the process of exploiting
vulnerabilities in target systems. It
includes a vast library of pre-built
exploits and payloads, as well as an
intuitive interface for creating custom
attacks.
• Nmap is a network exploration and
security auditing tool that can be used
to discover hosts and services on a
network, as well as identify potential
vulnerabilities. Its flexible scripting
engine allows for sophisticated
scanning and reporting capabilities.
10
• Wireshark is a network protocol analyzer that captures and analyzes
network traffic in real-time. It can be used to troubleshoot network
issues, as well as identify and exploit vulnerabilities in network
protocols.
11
Step 1: Pre-Engagement Analysis
Before even planning a test, it’s
imperative that you along with your
security provider discuss topics such as
the scope of the test, budget, objectives,
etc. Without these, there won’t be a clear
enough direction for the test, and will
result in a lot of wasted effort
Step 2: Information gathering
Before commencing the pen test, the
tester will attempt to find all publicly
available information about the system
and anything that would help in breaking
in. These would assist in creating a plan of
action as well as reveal potential targets.
12
Step 3: Vulnerability assessment
• In this stage, your application is checked for security vulnerabilities by
analyzing your security infrastructure and configuration. The tester searches
for any opening or security gaps that can be exploited to break into the
system.
Step 4: Exploitation
• Once the tester is armed with the knowledge of vulnerabilities present in the
system, they will start exploiting them. This will help in identifying the nature
of the security gaps and the effort required to exploit them.
Step 5: Post-exploitation
• Removing any executables, scripts, and temporary files from compromised
systems
• Reconfiguring settings back to the original parameters prior to the pen test
• Eliminating any rootkits installed in the environment
• Removing any user accounts created to connect to the compromised
system
13
Step 6: Reporting
Everything done during this security penetration testing is documented in a
detailed manner along with steps and suggestions to fix the flaws in the
security. Since the nature of the report is highly sensitive, it is ensured that it is
safely delivered to authorized personnel. Testers often have meetings and
debrief with executives and technical teams to help them understand the
report.
Step 7: Resolution
Once the target organization obtains the detailed report upon the scan
completion of its assets and its security, it is used to rectify and remedy the
vulnerabilities found. This helps avoid any breaches and threats to security.
14
Step 8: Rescanning
Upon the completion of patching of vulnerabilities based on the penetration
testing report provided, a rescan is conducted to scan the new patches to test
their air tightness. The application is rescanned to find any additional or new
vulnerabilities that could have risen from the patching.
Once this final step is completed and no vulnerabilities have been detected, the
organization or asset is said to be secure and is provided with a penetration test
certificate that is publicly verifiable and adds visible authenticity.
15
Challenges in Penetration Testing
Continuously changing environments
Fast release cycles are difficult to keep up
with regarding penetration tests, as they
must revised and rerun quickly as fast.
Assessing your true posture and risk in
these changing environments becomes a
challenge.
Rapid growth
Unsurprisingly, an expanding business
often means an expanding attack surface.
Adjusting pen tests accordingly can
almost feel like building the plane while
it’s already in flight.
16
Cybersecurity skills shortages
Within small internal security teams, knowledge of the latest techniques
used by attackers is often scarce.
Cyber threats are evolving
Even with more frequent pen testing, the rate that cybersecurity attack
methods evolve pose significant difficulties for businesses. To maintain the
knowledge needed internally is often insurmountable.
17
ADVANTAGES OF PENETRATION TESTING
• Putting yourself in a hacker's position
can help identify your vulnerabilities.
• Identify and resolve system
vulnerabilities
• Gain valuable insights into your digital
systems
• Establish trust with your clientele
18
• Mistakes can be costly
• Determining the test conditions
• Testing could be unethical
• Cybercriminals are using the same
techniques simulated attack.
DISADVANTAGES OF PENETRATION TESTING
19
In conclusion, Penetration Testing
executed when the application is
working properly. Then a different type
of testing method applied to the
application, depending upon the
requirement of the application. It finds
vulnerable areas of application in
advance by an authorized hacker so that,
it cannot be hacked by any unethical
hacker.
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The Art of Penetration Testing in Cybersecurity.

  • 2. Index 1. Purpose Of Penetration Testing 2. Types of Penetration Testing 3. 3 Different Approaches To Penetration Testing 4. Penetration Testing Methodologies 5. 8 Phases of Penetration Testing 6. Penetration Testing Tools 7. Challenges in Penetration Testing 8. Advantages Of Penetration Testing 9. Disadvantages Of Penetration Testing 10. Conclusion
  • 3. Purpose Of Penetration Testing • We find vulnerabilities before hackers do. • Identify weaknesses that threaten the integrity of your web resource or network by undergoing the simulated attack. • Prevent breaches and create a robust security posture. • Ensure the security of the data and continuous workflow with the help of experienced ethical hackers.
  • 4. 4 1. Penetration testing is a crucial aspect of modern cybersecurity, and it involves identifying vulnerabilities in a system by simulating an attack. There are different types of penetration testing, including network testing, web application testing, and wireless testing. 2. Network testing involves evaluating the security of a network, 3. web application testing focuses on finding vulnerabilities in web applications. 4. Wireless testing is used to identify weaknesses in wireless networks, such as those used for Wi-Fi. Types of Penetration Testing
  • 5. 5 White Box Penetration Testing In a white box test, is also called as Clear box and Transparent box testing, Here the pen tester has a complete knowledge and familiar to access all the source code of the application and software architecture. Black Box Penetration Testing As you have guessed correctly, in black box penetration testing is also called as real-world cyber attack. The tester has no knowledge of the system and designs of architecture here the tester will use
  • 6. 6 the different techniques to break the system or infrastructure. Gray Box Penetration Testing In a Gray box test, it will blend together the White & Black box test, Here the tester have a partial knowledge of understanding the infrastructure and system, Those tester are only focus on those area of the system they most understand
  • 7. 7 Penetration Testing Methodologies • Penetration testing is a critical component of ensuring the security of digital systems. There are several methodologies that can be employed when conducting a penetration test, including the Open-Source Security Testing Methodology Manual (OSSTMM) and the Penetration Testing Execution Standard (PTES). These methodologies provide a structured approach to testing and help ensure that all aspects of the system are thoroughly evaluated.
  • 8. 8 • The OSSTMM(Open-Source Security Testing Methodology Manual), In this methodology the pen tester will do the manual test, Here the IT team & Security testing team Will work together. • The PTES(Penetration Testing Execution Standard), this on other way to do pen test , It provides a more comprehensive framework This Metrology is used for automation pen test with the help of some Tools.
  • 9. 9 Penetration Testing Tools • Metasploit is a powerful framework that allows penetration testers to automate the process of exploiting vulnerabilities in target systems. It includes a vast library of pre-built exploits and payloads, as well as an intuitive interface for creating custom attacks. • Nmap is a network exploration and security auditing tool that can be used to discover hosts and services on a network, as well as identify potential vulnerabilities. Its flexible scripting engine allows for sophisticated scanning and reporting capabilities.
  • 10. 10 • Wireshark is a network protocol analyzer that captures and analyzes network traffic in real-time. It can be used to troubleshoot network issues, as well as identify and exploit vulnerabilities in network protocols.
  • 11. 11 Step 1: Pre-Engagement Analysis Before even planning a test, it’s imperative that you along with your security provider discuss topics such as the scope of the test, budget, objectives, etc. Without these, there won’t be a clear enough direction for the test, and will result in a lot of wasted effort Step 2: Information gathering Before commencing the pen test, the tester will attempt to find all publicly available information about the system and anything that would help in breaking in. These would assist in creating a plan of action as well as reveal potential targets.
  • 12. 12 Step 3: Vulnerability assessment • In this stage, your application is checked for security vulnerabilities by analyzing your security infrastructure and configuration. The tester searches for any opening or security gaps that can be exploited to break into the system. Step 4: Exploitation • Once the tester is armed with the knowledge of vulnerabilities present in the system, they will start exploiting them. This will help in identifying the nature of the security gaps and the effort required to exploit them. Step 5: Post-exploitation • Removing any executables, scripts, and temporary files from compromised systems • Reconfiguring settings back to the original parameters prior to the pen test • Eliminating any rootkits installed in the environment • Removing any user accounts created to connect to the compromised system
  • 13. 13 Step 6: Reporting Everything done during this security penetration testing is documented in a detailed manner along with steps and suggestions to fix the flaws in the security. Since the nature of the report is highly sensitive, it is ensured that it is safely delivered to authorized personnel. Testers often have meetings and debrief with executives and technical teams to help them understand the report. Step 7: Resolution Once the target organization obtains the detailed report upon the scan completion of its assets and its security, it is used to rectify and remedy the vulnerabilities found. This helps avoid any breaches and threats to security.
  • 14. 14 Step 8: Rescanning Upon the completion of patching of vulnerabilities based on the penetration testing report provided, a rescan is conducted to scan the new patches to test their air tightness. The application is rescanned to find any additional or new vulnerabilities that could have risen from the patching. Once this final step is completed and no vulnerabilities have been detected, the organization or asset is said to be secure and is provided with a penetration test certificate that is publicly verifiable and adds visible authenticity.
  • 15. 15 Challenges in Penetration Testing Continuously changing environments Fast release cycles are difficult to keep up with regarding penetration tests, as they must revised and rerun quickly as fast. Assessing your true posture and risk in these changing environments becomes a challenge. Rapid growth Unsurprisingly, an expanding business often means an expanding attack surface. Adjusting pen tests accordingly can almost feel like building the plane while it’s already in flight.
  • 16. 16 Cybersecurity skills shortages Within small internal security teams, knowledge of the latest techniques used by attackers is often scarce. Cyber threats are evolving Even with more frequent pen testing, the rate that cybersecurity attack methods evolve pose significant difficulties for businesses. To maintain the knowledge needed internally is often insurmountable.
  • 17. 17 ADVANTAGES OF PENETRATION TESTING • Putting yourself in a hacker's position can help identify your vulnerabilities. • Identify and resolve system vulnerabilities • Gain valuable insights into your digital systems • Establish trust with your clientele
  • 18. 18 • Mistakes can be costly • Determining the test conditions • Testing could be unethical • Cybercriminals are using the same techniques simulated attack. DISADVANTAGES OF PENETRATION TESTING
  • 19. 19 In conclusion, Penetration Testing executed when the application is working properly. Then a different type of testing method applied to the application, depending upon the requirement of the application. It finds vulnerable areas of application in advance by an authorized hacker so that, it cannot be hacked by any unethical hacker.