What is penetration testing in cybersecurity?

Penetration testing is a way to “stress test” your IT infrastructure security.

Penetration techniques are used to evaluate the safety and security of the network
in a controlled manner. Operating systems, services, applications, and even the
behavior of the end user is assessed to validate existing defense mechanisms and
the efficacy of end-user security policies.
There are a few reasons to regularly perform penetration tests (or “pen tests”).
First and foremost, penetration testing can help ensure user data is secure,
identify security vulnerabilities, discover loopholes in the system, and assess the
overall strength of existing defense mechanisms. In addition, penetration testing
can help a business stay up-to-date with each new software release. As threats
evolve, financial and PI data must be secured iteratively—as new devices are added
to a system, transferring data among different end points requires constant
monitoring and assessment for security compliance.
Likewise, penetration testing has a few key benefits. It allows an MSP to
proactively showcase their expertise and skillfully manage vulnerabilities. It
saves money by allowing organizations to avoid network downtime. Penetration
testing methods can help an MSP’s customers meet regulatory requirements and avoid
fines. At the end of the day, it’s also an important tool to preserve an MSP’s
image, reputation, and customer loyalty.
Pen testing may sound similar to a vulnerability assessment, but the two
cybersecurity measures are not the same. A vulnerability assessment focuses on
identifying security issues within an organization. A list of vulnerabilities is
produced from an evaluation of cybersecurity and data storage vulnerabilities. A
penetration test, however, uses attack-simulated scenarios in a goal-oriented
approach to cybersecurity. The test is designed to hit specific targets, such as a
database, storage method, or designated file. The result of a pen test is not only
a list, but a methodology and map of specific points of weakness.
What are the phases of a penetration test?
There are six generally accepted penetration testing steps. They are planning;
reconnaissance and information gathering; scanning and discovery; attack and
gaining access; maintaining access and penetration; and risk analysis and
reporting. Depending on the frequency and type of penetration testing you wish to
perform, these phases may vary slightly from MSP to MSP.
1) Planning for penetration testing
The first phase of penetration testing involves determining the scope and goals of
the test. MSPs must work with their clients to figure out the logistics,
expectations, objectives, goals, and systems to be addressed. The planning phase
will establish whether you are using a black box, white box, or gray box
penetration testing method.
2) Reconnaissance and information gathering
In this phase, the “hacker” or penetration tester seeks to discover as much
information as possible about their target. They will gather information about end
uses, systems, applications, and more. The information will be used to be precise
in the penetration test, using a complete and detailed rundown of systems to
understand what, exactly, needs to be addressed and evaluated. Some of the methods
used during this phase may include search engine queries, domain name searches,
internet footprinting, social engineering, and even looking up tax records to find
personal information.
3) Scanning and discovery
The scanning and discovery phase is built to discover how the target system is
going to respond to various attempts at intrusion. The penetration tester will most
likely use automated penetration test tools to scan for initial vulnerabilities.
Static analysis and dynamic analysis are two types of approaches used by the
penetration tester. Static analysis inspects an application’s code in an attempt to
predict how it will react to an incursion. Dynamic analysis looks at an
application’s code as it runs, providing a real-time view of how it performs. Other
aspects that a pen tester will discover include network systems, servers, and
devices, as well as network hosts.
4) Attack and gaining access
Once the pen tester has gained a complete understanding of the scope and components
to be tested, they will attack in a simulated and controlled environment. Mimicking
an actual cyberattack, the tester may take control of a device to extract data;
perform a web application attack, such as cross-site scripting or SQL injection; or
perform a physical attack, as mentioned previously. The goal of this phase is to
see how far the tester can get into an IT environment without detection. The scope
of the project should determine where the limits of the test should end to protect
PI and other sensitive data.
5) Maintaining access and penetration
Once a pen tester has successfully compromised their target, they should try to
expand their access and maintain their presence for as long as possible. Again, the
goal is to imitate a real-world bad actor as much as possible. The penetration
tester in this phase will try to expand their permissions, find user data, and
remain stealthy while running their programs deeper into the IT infrastructure. For
example, the penetration tester may try to escalate their privileges to the role of
administrator. The goal here is to remain undetected in the system for as long as
possible and to try to get at the most sensitive data (according to the project
scope and goals).
6) Risk analysis and reporting
The last phase of penetration testing is the assessment and reporting phase. Once
the penetration tester has been “discovered,” or the timeline for the project has
been completed, a final report will be generated. The report should provide a
summary of the testing, details of each step the pen tester took to infiltrate
systems and processes, details of all vulnerabilities, how they cleaned up after
the stress test, and suggestions for security fixes. A good penetration tester will
also be able to determine the value of the compromised systems—i.e., how much
financial impact would their incursion cost? To do this, a penetration tester uses
some penetration testing tools.

the following penetration testing types:

1. Network Penetration Testing
2. Web Application Penetration Testing
3. Wireless Penetration Testing
4. Physical Penetration Testing
5. Social Engineering Penetration Testing
6. Client-Side Penetration Testing
7. IoT Penetration Testing
8. Mobile App Penetration Testing
9. Red Team Penetration Testing
1. Network Penetration Testing
Network penetration testing finds and exploits the most exposed vulnerabilities in
network infrastructure such as servers, firewalls, and switches. This type of
testing can help protect your business from common network-based attacks, such as:
* Firewall misconfiguration and firewall bypass
* IPS/IDS evasion
* Router attacks
* DNS-level attacks
* Zone transfer attacks
* Switching or routing-based attacks
* SSH attacks
* Proxy server attacks
* Attacks on unnecessary open ports
* Database attacks
* Man-in-the-middle (MitM) attacks
* FTP/SMTP-based attacks
2. Web Application Penetration Testing
Web application penetration testing is used to find vulnerabilities in web-based
applications. It uses a three-step process:
1. Reconnaissance—discovering information about web servers, operating systems,
services, resources, and more used by the web application
2. Discovery—finding vulnerabilities in the web applications and planning attack
vectors to be used in the penetration test.
3. Attack—exploiting a vulnerability to gain unauthorized access to the application
or its data.
Penetration testing of web applications can identify security vulnerabilities in
databases, source code, and backend networks of web-based applications. It can not
only identify vulnerabilities but also help prioritize them and provide solutions
to mitigate them.
3. Wireless Penetration Testing
Wireless communications are services that allow data to move in and out of networks
and must be protected from unauthorized access and data exfiltration. Wireless
penetration testing is used to identify risks associated with wireless networks and
evaluate weaknesses such as:
* Deauthentication attacks
* Misconfiguration of wireless routers
* Session reuse
* Unauthorized wireless devices
4. Physical Penetration Testing
If a threat actor has physical access to a server room or other sensitive facility,
they can potentially compromise the entire network, which can have devastating
effects on business, customers, and partnerships. Physical penetration testing can
help secure an organization’s physical assets from threats such as social
engineering, tailgating, and badge cloning.
Physical penetration testing finds weaknesses in physical controls such as locks,
doors, cameras, or sensors, and allows the organization to quickly remediate
defects.
5. Social Engineering Penetration Testing
When it comes to security, users are often considered the weakest link of the
security chain, and are a common target for attackers. Social engineering
penetration testing focuses people and processes in the organization and the
security vulnerabilities associated with them. It is performed by ethical hackers
who attempt social engineering attacks which are commonly experienced in the
workplace, such as phishing, USB dropping, and spoofing.
The goal is to identify vulnerable individuals, groups, or processes, and to
develop pathways for improving security awareness.
6. Client-Side Penetration Testing
Client-side penetration testing tests can uncover security vulnerabilities in
software running on client computers, such as web browsers, media players, and
content creation software packages (such as MadCap Flare, Adobe Framemaker, or
Adobe RoboHelp). Attackers often compromise client-side software to gain access to
company infrastructure.
Perform client-side testing to identify specific network attacks, such as:
* Cross-site scripting attacks (XSS)
* Clickjacking attacks
* Cross-origin resource sharing (CORS)
* Form hijacking
* HTML injection
* Open redirection
* Malware infection
7. IoT Penetration Testing
IoT penetration testing looks for security vulnerabilities in connected ecosystems,
including vulnerabilities in hardware, embedded software, communication protocols,
servers, and web and mobile applications related to IoT devices.
The types of tests conducted on hardware, firmware, and communication protocol
depend on the connected device. For example, some devices may require data dumping
through electronic components, firmware analysis, or signal capture and analysis.
8. Mobile App Penetration Testing
Mobile application penetration testing is performed on mobile applications
(excluding mobile APIs and servers), including both static and dynamic analysis:
* Static analysis extracts source code and metadata and performs reverse
engineering to identify weaknesses in application code.
* Dynamic analysis finds application vulnerabilities while the application is
running on a device or server.
9. Red Team Penetration Testing
Red team penetration is an advanced testing technique based on military training
exercises. It uses an adversarial approach, allowing organizations to challenge
their security policies, processes, and plans. Blue teaming, or “defensive
security,” involves detecting and withstanding red team attacks and real-life
adversaries.
Red teaming combines physical, digital, and social contexts to simulate a
comprehensive real-life attack scenario, making it distinct from standard
penetration testing. It encompasses tasks related to the various types of
penetration testing. While a standard pentest aims to identify as many
vulnerabilities as possible in a set timeframe, it is typically limited by
artificial restrictions such as the task scope.
Regular penetration tests are important, but they don’t provide realistic
conditions, such as combined attack techniques. Red teaming allows security teams
to assess the overall environment and understand how its components function
together. It requires critical thinking to identify new, complex vulnerabilities.
Red team assessments are generally more time-consuming than standard penetration
tests, often taking several months to complete. This complex nature makes red
teaming a rare operation, viable only for large organizations.
Blue/Red Teaming
Blue teaming and red teaming are terms used primarily in the context of
cybersecurity to describe different approaches to testing and improving the
security posture of an organization or system.
Blue Teaming:
* Blue teaming involves the internal security team of an organization (or sometimes
an external team) that defends against simulated attacks from red teamers.
* The primary focus of blue teaming is on defense and mitigation. Blue teams
analyze and strengthen defenses, monitor for security threats, and respond to
incidents.
* Blue team activities include penetration testing, vulnerability assessments,
security monitoring, incident response, and generally ensuring compliance with
security policies and standards.
* The goal of blue teaming is to strengthen overall security posture by improving
defenses, enhancing incident response capabilities, and reducing vulnerabilities.
Red Teaming:
* Red teaming involves a team (internal or external) that simulates real-world
cyberattacks to test the effectiveness of an organization's defenses.
* Red teaming is focused on offense and attack simulation. The red team operates as
if they were actual attackers, attempting to breach systems, steal data, or disrupt
operations.
* Red team activities can include targeted phishing attacks, attempting to exploit
vulnerabilities, social engineering, and attempting to escalate privileges to gain
unauthorized access.
* The goal of red teaming is to identify weaknesses in security controls,
processes, and personnel. By exposing vulnerabilities through realistic attack
scenarios, organizations can better understand their risk exposure and improve
their defenses.

While blue teams defend and red teams attack, both work together to improve
security. Red team findings help blue teams identify and prioritize weaknesses to
fix, while blue teams' defenses challenge red teams to innovate and find new ways
to breach defenses.
The iterative process of red teaming followed by blue team response and improvement
leads to a more resilient security posture over time.

Strategies of Testing,
In penetration testing (pen testing), there are several strategies and
methodologies that testers employ to effectively identify and exploit
vulnerabilities within an organization's systems, networks, and applications. These
strategies help ensure thorough coverage and accurate assessment of security
posture.
Here are some common strategies used in penetration testing:
1. Black Box Testing:
* In black box testing, the penetration tester has little to no prior knowledge
of the target environment. This simulates an external attacker who has no insider
information about the systems. It helps in identifying vulnerabilities that are
visible from an external perspective.
2. White Box Testing:
* White box testing, also known as clear box testing or transparent testing,
provides the penetration tester with full knowledge of the internal workings and
architecture of the systems being tested. This allows for a more in-depth
assessment of vulnerabilities that might not be easily discoverable from an
external perspective.
3. Gray Box Testing:
* Gray box testing strikes a balance between black box and white box testing.
The tester has partial knowledge of the internal workings of the systems, typically
provided by the organization's IT or security team. This approach helps simulate an
attack scenario where an insider threat or a compromised insider may be involved.
4. Internal Testing:
* Internal testing focuses on assessing the security of systems and networks
from within the organization's internal network. It simulates attacks that could
occur from employees, contractors, or others who have legitimate access to internal
resources.
5. External Testing:
* External testing evaluates the security of systems and networks from an
external perspective, as would be the case with malicious attackers attempting to
exploit vulnerabilities over the internet. It includes testing web applications,
email servers, VPNs, and other externally accessible systems.
6. Targeted Testing:
* Targeted testing involves focusing on specific systems, applications, or areas
of concern identified by the organization or based on the results of initial
reconnaissance and vulnerability scanning. It allows for a more concentrated effort
on critical assets or areas with higher risk.
7. Compliance Testing:
* Compliance testing ensures that the organization meets specific regulatory
requirements or industry standards (e.g., PCI DSS, HIPAA). It verifies that
security controls and processes are implemented correctly to protect sensitive data
and comply with legal obligations.
8. Social Engineering Testing:
* Social engineering testing assesses the effectiveness of security controls
against human vulnerabilities. It involves techniques such as phishing emails,
phone calls, or physical entry attempts to manipulate individuals into revealing
sensitive information or granting unauthorized access.
9. Blended Testing:
* Blended testing combines multiple testing strategies and methodologies to
provide a comprehensive assessment of an organization's security posture. For
example, it might include a combination of external and internal testing, along
with social engineering techniques.
10. Continuous Testing:
* Continuous testing integrates penetration testing into an organization's
ongoing cybersecurity program. It involves regular assessments to detect and
mitigate new vulnerabilities as they arise, ensuring that security defenses remain
robust over time.

Non-Disclosure Agreement Checklist

a checklist for a Non-Disclosure Agreement (NDA) tailored for penetration testing
engagements:
1. Parties Involved:
* Identify the full legal names and addresses of the parties entering into the
agreement (client and penetration testing service provider).
2. Definition of Confidential Information:
* Clearly define what constitutes confidential information. This should include
specifics such as system configurations, network diagrams, proprietary algorithms,
source code, sensitive business plans, and any other information considered
confidential.
3. Purpose of Disclosure:
* State that the disclosure of confidential information is solely for the
purpose of conducting penetration testing and related security assessments.
4. Duration of Confidentiality:
* Specify the duration for which the confidentiality obligations will apply.
Typically, this extends beyond the completion of the engagement to cover any
residual information or insights gained during testing.
5. Permitted Use of Information:
* Outline the permissible uses of the confidential information by the
penetration testing team. This includes activities directly related to conducting
the tests, documenting findings, generating reports, and communicating results to
the client.
6. Restrictions on Disclosure:
* Prohibit the penetration testing team from disclosing any confidential
information to third parties without explicit written consent from the client. This
includes not disclosing findings, vulnerabilities, or sensitive details to
unauthorized individuals or entities.
7. Security Measures:
* Specify the security measures that the penetration testing team will implement
to protect the confidentiality of the client's information. This may include
encryption of sensitive data, restricted access controls, and secure storage
practices.
8. Return or Destruction of Information:
* Require the penetration testing team to return or securely destroy all
confidential information provided by the client at the conclusion of the
engagement, unless otherwise instructed by the client.
9. Liability and Indemnification:
* Address liability issues, including limitations of liability for both parties,
indemnification clauses to protect against claims arising from breaches of
confidentiality, and procedures for resolving disputes related to the NDA.
10. Legal Jurisdiction and Governing Law:
* Specify the jurisdiction and governing law that will apply to the
interpretation and enforcement of the NDA. This ensures clarity on legal recourse
in case of any disputes or breaches.
11. Signatures and Execution:
* Include signature blocks for authorized representatives of both parties, along
with the date of execution. Ensure that all parties sign and retain a copy of the
executed NDA for their records.
12. Review and Updates:
* Include provisions for reviewing and updating the NDA as necessary,
particularly if there are changes in the scope of testing, the parties involved, or
legal requirements.
Phases of hacking
1 Reconnaissance: -
Reconnaissance is also known as information gathering. Gathering the data of target
to known weak point that helpful to attack on target. Gathering information about
target by scanning on internet, thought social engineering, from social networking
site and web services.
Gathering of information about targeted organization by websites visited.
Performing whois, DNS lookup, and network footprinting for gathering information
about target. Perform system scan to identify open ports and services. In the
reconnaissance sensitive information is gather about the target.
Network Footprinting is a method of collecting a data from targeted network. These
data include important areas such as:
* Finding out specific IP addresses
* TCP and UDP services
* Identifies vulnerabilities
There are two types of reconnaissance:
I Active Reconnaissance: -
By this method attacker gather the information about the target by interacting with
that. The attacker comes in direct contact with victim.
II Passive Reconnaissance: -
In this method attacker do not comes in direct contact with victim.
Gather information from publicly available information, news etc.
The following information is crucial to perform an attack:
* Naming conventions
* Services on the network
* Server’s handling workloads in the network
* IP Addresses
* Names and Login credentials of users connected to the network
* Physical location of target machine
2 Scanning: -
Scanning is like active reconnaissance in this phase attacker use the information
gather in reconnaissance for gathering specific information gather in
reconnaissance for gathering specific information by scanning network. Attacker can
gather critical information such as the mapping of systems, routers, and firewalls
by using ICMP Tool Traceroute.
Scanning Involves three types: -
I Port Scanning: -
In this scanning scan targeted system ports and gather information like open ports,
live systems, various services running on the host.
II Vulnerability Scanning: -
In this scanning gather information of weaknesses or vulnerability of targeted
system. This information help to exploit.
III Network Mapping: -
In this network related information is gather. Such as Network Topology, routers,
firewalls, servers, host and drawing a network diagram with the available
information.
There are many tools available for scanning but some popular tools are commonly use
for ethical hacking are:
* SNMP Sweepers
* Ping sweeps
* Network mappers
* Vulnerability scanners
3 Gaining Access: -
In this phase attacker gaining access of targeted system /network using various
tools or methods. After entering into a system, attacker increase his privilege has
to administrator level so he can install an application be needs to modify data or
hide data.
There are many options, for example:
* Phishing attack
* Man in the middle attack
* Brute Force Attack
* Spoofing Attack
* Dos attack
* Buffer overflow attack
* Session hijacking
* BEC Attack
* Injection attacks
* XML External entity processing
* Using components with known velnerabilities
4 Maintaining Access: -
In this phase the attacker tries to retain his ownership of the system.
The aim is to maintain the access to the access to the target until he finishes the
tasks he planned to accomplish in that target.
5 Clearing Tracks: -
In this phase intelligent attacker always clears all evidences. Attacker must
change MAC of attacker’s system. Use at least on VPN to hide their identity.
He/she does following to clearing a tracks:
* Clearing the cache and cookies
* Modifying registry values
* Modifying/corrupting/deleting the values of Logs
* Clearing out Sent emails
* Closing all the open ports
* Uninstalling all applications that he/she be used

Open-source/proprietary Pen-test Methodologies

### Open-Source Methodologies

1. **OWASP Testing Guide**

- **Overview**: A comprehensive guide for web application security testing.
- **Phases**:
- Information Gathering: Collecting data about the target.
- Configuration and Deployment Management Testing: Checking for configuration
weaknesses.
- Identity Management Testing: Testing authentication mechanisms.
- Authorization Testing: Ensuring proper access control.
- Session Management Testing: Checking for vulnerabilities in session
handling.
- Input Validation Testing: Testing for injection flaws and other input-
related vulnerabilities.
- Error Handling: Checking how errors are handled and whether they leak
information.
- Cryptography: Assessing the use of cryptographic mechanisms.
- Business Logic Testing: Testing for flaws in the application’s logic.
- Client-Side Testing: Assessing client-side vulnerabilities.
- **Documentation**: Detailed test cases, attack vectors, and remediation
advice.
2. **PTES (Penetration Testing Execution Standard)**
- **Overview**: A framework to standardize the execution of penetration tests.
- **Phases**:
- Pre-engagement Interactions: Defining scope, rules of engagement, and
objectives.
- Intelligence Gathering: Collecting information about the target.
- Threat Modeling: Identifying potential threats and attack vectors.
- Vulnerability Analysis: Identifying vulnerabilities in the target
environment.
- Exploitation: Attempting to exploit identified vulnerabilities.
- Post-Exploitation: Determining the impact and persistence of exploitation.
- Reporting: Documenting findings and providing remediation recommendations.
- **Focus**: Providing a structured approach to cover all aspects of a pen test.

3. **OSSTMM (Open Source Security Testing Methodology Manual)**

- **Overview**: A peer-reviewed methodology for security testing.
- **Phases**:
- Intelligence Gathering: Understanding the target environment.
- Interaction: Directly engaging with the target.
- Data Analysis: Interpreting the results of testing activities.
- **Focus**: Emphasizes measurement of security in operational environments.
- **Metrics**: Uses the RAV (Risk Assessment Value) model to quantify security
levels.

4. **NIST SP 800-115**
- **Overview**: Provides guidelines for organizations to conduct penetration
testing.
- **Phases**:
- Planning: Defining objectives, scope, and rules of engagement.
- Execution: Conducting the actual penetration test.
- Post-Execution: Analyzing results, reporting findings, and suggesting
remediation.
- **Documentation**: Includes templates and checklists for planning and
reporting.

### Proprietary Methodologies

1. **CREST (Council of Registered Ethical Security Testers)**

- **Overview**: A structured approach to penetration testing, with a focus on
certification and accreditation.
- **Phases**:
- Scoping and Preparation: Defining the test's scope and preparing for the
engagement.
- Testing: Conducting the pen test using certified professionals.
- Reporting: Detailed documentation of findings and recommendations.
- **Focus**: Ensuring high standards and consistency in pen testing services.

2. **CHECK (UK Government's IT Health Check Scheme)**

- **Overview**: A framework for government and public sector organizations in
the UK.
- **Phases**:
- Pre-Engagement: Planning and defining the scope of the test.
 - Testing: Conducting thorough assessments using approved methodologies.
- Reporting: Providing detailed reports with findings and remediation
strategies.
- **Focus**: Ensuring compliance with UK government standards.

3. **TIBER-EU (Threat Intelligence-based Ethical Red Teaming)**

- **Overview**: A framework developed for the European financial sector.
- **Phases**:
- Preparation: Planning and scoping the red teaming exercise.
- Testing: Conducting threat intelligence-led red teaming activities.
- Reporting: Documenting the findings and providing improvement
recommendations.
- **Focus**: Enhancing the resilience of financial institutions against
sophisticated cyber attacks.

4. **SANS Institute Methodology**

- **Overview**: Practical and hands-on approach to penetration testing.
- **Phases**:
- Reconnaissance: Gathering information about the target.
- Scanning: Identifying vulnerabilities in the target environment.
- Exploitation: Attempting to exploit vulnerabilities.
- Post-Exploitation: Assessing the impact and establishing persistence.
- Reporting: Documenting findings and suggesting remediation.
- **Focus**: Emphasizing real-world scenarios and practical skills.