The Ultimate Manual for Organizing and Getting Ready for Penetration Testing

How to Conduct Effective Penetration Testing

To effectively plan and prepare for penetration testing, the following actions are required; these will be described in more depth below:

1. Create a team: Choose the security leaders who will oversee the penetration testing effort, including a central organizer or primary point of contact. Clearly define jobs and responsibilities and set goals.
2.Participants: Determine the important decision-makers and stakeholders. What are their responsibilities? At what point in the penetration testing process will their approvals be required?
3.Make a plan for the project: The scope of the testing, the particular systems and assets to be tested, the timetable, the goals, and the anticipated results should all be clearly outlined in the project plan.

4. Select a testing approach: Depending on the scope, choose the appropriate testing methodology. Black Box, White Box, and Gray Box testing are common approaches. Additionally, think about the particular methods your company wants to use, such as external-facing web app testing, API fuzzing, social engineering, etc.
5. Assistance to the security team: Think about what assistance the security team will require and if the company has the necessary funds, resources, and experience. Assess if an outside pentesting service provider is required or if the project will be managed internally. When choosing an outside service provider, find out what kind of assistance and knowledge they provide.

6. Interacting with the supplier: When selecting a vendor, make sure you ask the appropriate questions after conducting some research. Among other things, you might want to know if penetration testing is a part of your main business.

• Are you insured against professional liability?
• Are you able to offer testimonials or references?
• Do you possess the appropriate CREST or ISO 9001 pentesting certifications?
• What credentials do your pentesters possess?
• How do you keep up with the most recent exploits and vulnerabilities?
• What are your pricing policies and pentesting methodology?

7. Report Debrief: It will be crucial to draft a thorough report outlining the pentesting results and remedial suggestions. Discuss the results and possible risks with your team and, if you’re utilizing a pentesting service provider, debrief. Work closely with stakeholders to make sure that the results are understood and that a schedule for prompt correction is agreed upon.

1. Steps to take for remediation: Compile a report with thorough results and offer precise instructions on how to rank vulnerabilities according to their seriousness, along with action items to reduce the risks. Continue to communicate effectively, take responsibility, and resolve issues promptly.
2.Test and validate: More testing could be required to confirm that the remediation efforts were successful and that they have been addressed. Verify that the pentesting procedure did not reveal any new problems.

Getting Ready for Services in Penetration Testing

Recognize Your Attack Surface

It is critical to have full awareness of your cyber assets in order to comprehend your attack surface. When determining your assault surface, there are three primary factors to take into account:

1. Attack Surface Visibility:

Find unmanaged and hidden cyber assets

As an organization’s digital footprint expands, attackers are exploiting the attack surface more and more. This increased attack surface makes it more difficult for security professionals to safeguard their IT environment while also making it simpler for malicious actors to identify vulnerabilities. It can be difficult to identify all cyber assets and possible weaknesses. It is practically impossible to evaluate and convey an organization’s risk exposure if it does not have complete insight into every potential attack vector.

2. Setting Risk as a Priority: Using risk to inform decisions

Organizations are left susceptible when risk is monitored and assessed without ongoing evaluations. Security executives must have a good understanding of the main variables affecting risk in order to inform stakeholders and direct strategic choices. Regular risk assessments give DevSecOps teams useful information that they may use to improve defenses, address vulnerabilities, and stop security breaches.

3. Risk Mitigation: Lowering the Attack Surface Risk

Due to time and visibility constraints, security professionals frequently find themselves responding to attacks without the necessary direction to foresee hazards. A broad attack surface necessitates proactive measures to identify, evaluate, and manage cyber risk prior to an attacker striking, in addition to maximizing threat defense.

Establish the Scope

Before testing starts, take into account the following while deciding on a penetration test’s scope:

1. Determine What to Test:

Which resources and domains would the companies wish to test? This entails determining which crucial networks, apps, systems, or data are at risk of intrusion.

2. Set Goals:

Security teams should also think about the business objectives for penetration testing. Whether the goal is to test endpoints that can be circumvented or to concentrate on human security levels using phishing techniques, it’s critical to identify any potential weak points in particular areas or to test the entire infrastructure.

3. Compliance Requirements:

Certain sectors have particular rules that may specify what your penetration test must contain. The testing scope can be reduced by being aware of the regulations that the businesses must adhere to as well as the testing needs.

This information, along with other crucial details like servers, domains, organizational architecture, IP-addressed devices, permitted user credentials (based on the pentesting technique), and any exclusions, should be at the disposal of security professionals.

Which assets are frequently tested?

Outside Resources

Web-based applications:

Web applications are the external asset or assets that most frequently benefit from penetration testing services. Pentesting external web apps finds possible attack routes and fixes certain vulnerabilities based on the technology and application design. These are frequently referred to as internet- or public-facing programs that are available online. SQL injections, XSS, authentication and/or business logic errors, credential stuffing, and other vulnerabilities are the most often discovered vulnerabilities.

Furthermore, mobile apps, APIs, cloud computing, external networks, the Internet of Things, and safe code review are just a few examples of the external assets that can be subject to penetration testing services.

Internal Resources

Network Infrastructure: Internal networks and systems are the subject of the most frequent penetration tests for internal assets. It is no longer the case that internal networks are more secure than systems that face the outside world, as most security professionals and businesses believe. When an attacker manages to get access to an internal network, their objective is to migrate laterally across systems, increase their privileges, and steal sensitive and private information. Misconfigured active directories (ADs), weak passwords or inadequate authentication, and out-of-date or unpatched software and systems are the most frequently discovered vulnerabilities.

Internal apps, APIs and API endpoints, workstations and laptops, Thick Client apps, and testing at every stage of the software development life cycle (SDLC) are just a few examples of the internal assets that might be subject to penetration testing services.

Which Penetration Testing Type Is Best for You?

Finding the best methodology will depend on what has been specified in your scope. There are various kinds of penetration testing approaches. Penetration testing techniques have changed, and businesses are no longer dependent on the conventional penetration testing provided by large consulting organizations. The various pentesting techniques that are available and how they are frequently applied to get the best results are listed below.

1. Traditional Pentesting:

Big international consulting organizations provide this project-based, structured, and conventional method. External security specialists conduct tests on particular systems, networks, or apps as part of this highly interactive pentesting process, which has a set scope and timetable. While providing stakeholders and auditors with a sense of assurance can make this kind of traditional pentesting appear more trustworthy, it can also be quite expensive because these companies frequently charge a premium for their services, making it unaffordable for small or mid-sized businesses.

Because traditional pentesting often takes place once a year or twice a year, there may be gaps in security visibility between evaluations. Because attack surfaces are always changing, new vulnerabilities might go unnoticed throughout this time.

Finally, the feedback loops can appear slow, and these classic engagements typically take a long time to start going. Some vulnerabilities might not be relevant by the time results are delivered, which could take weeks or months.

2. Autonomous Pentesting:

Automated penetration testing eliminates the need for continual human involvement by performing security assessments using automated tools, scripts, and artificial intelligence. It may mimic various attack situations, find vulnerabilities, and offer remedial suggestions, just like other pentesting techniques. The same operations that would require manual testing can be completed by automated pentesting, except it is done continuously or on a predetermined timetable.

Large network infrastructures may be efficiently scanned by automated pentesting, which mainly concentrates on networks and network services. Because it can be scheduled on a regular basis and is less likely to be human error-prone, this type of pentesting can also perform static and dynamic scans of web applications to identify common vulnerabilities, as well as APIs and API endpoints, cloud, and external-facing assets like public websites, databases, and networks.

Automated pentesting provides cost savings, scalability, and speed. Regular pen tests can be conducted by autonomous tools, which offer continuous monitoring and make it possible to find vulnerabilities as soon as they appear. Automated technologies, however, frequently concentrate on well-known, common vulnerabilities and could miss more intricate or subtle flaws that a human tester could find.

3. Penetration Testing as a Service (PTaaS):

PtaaS is a hybrid approach to penetration testing that combines human-led and automated pentesting, offering advantages including repeatability, speed, and scale. Certified and extremely talented ethical hackers carry out manual pentesting, looking for weaknesses in a network, application, or system. Manual pentesting is a thorough, human-driven process that, in contrast to automated methods, enables greater skill, intuition, and adaptability in identifying intricate vulnerabilities.

PTaaS can be customized to delve further into particular areas of concern and covers the complete IT infrastructure, both internal and external. Experts in manual pentesting can adopt the mindset of attackers, employing methods similar to those employed by malevolent actors, and tailor particular use cases or unusual configurations for testing to fit the IT environment of the company. If manual testers run into unforeseen situations or defenses, they can also modify their strategy.

Finding complicated and sophisticated vulnerabilities, including business logic issues, requires a hybrid approach to penetration testing that combines the creativity and adaptability of manual testing with the efficiency, scalability, and cost-effectiveness of continuous automated testing. By combining the depth of manual testers with the speed and scope of automated tools, it is possible to guarantee more complete and in-depth coverage of the attack surface.

Getting Ready for Your Penetration Test

Selecting the Best Pentesting Provider and Services

Choosing between internal and external pentesting resources is a crucial issue that is frequently influenced by goals and scope. There are distinct benefits and drawbacks to using an organization’s own internal pentesting team, an outside pentesting company with their own in-house pentesting specialists, and outside resources like crowdsourcing.

Testing for Internal Penetration in Organizations

• Insider Perspective: Offers an insider’s perspective by simulating an internal attack.
  Internal Systems: Able to offer a comprehensive evaluation of internal systems, including privilege escalation and lateral movement.
• Cost-effectiveness: Pentesting can frequently be less expensive if the organization’s resources and experience are still available, eliminating the need for needless outside expenses.
• Continuous Improvement: More frequent updates and enhancements might result from internal teams’ ability to conduct ongoing testing and monitoring.

When to utilize it: Internal penetration testing works best for testing internal policies, detecting and reducing insider risks, and making sure internal systems are safe.

External Pentesting Using Service Provider and Internally Trained Professionals

• Specialized Knowledge: A penetration testing service provider’s in-house pentesting specialists are highly skilled, qualified ethical hackers who hold the most up-to-date industry certifications, including CREST, OSCP, OSCE, CEH, CISA, CISM, SANS, and others.
• Unbiased View: Outside pentesters can offer an objective perspective, frequently pointing out weaknesses that inside teams might overlook.
  Standardization: Adhere to established procedures and standards that are in line with the OWASP, CREST, NIST, and MITRE ATT&CK approaches.
• help and Customization: In addition to delivering help during the whole testing process and the opportunity to modify security testing to fit your business needs, pentesting companies also offer the advice required to select the best pentesting technique.

When to utilize it: When resources and experience are scarce, external pentesting works best. For more precise and reliable results, it is perfect for evaluating assets that face the outside world as well as those that face the inside utilizing defined techniques. Additionally, it works best for getting an objective assessment of your security posture and guaranteeing regulatory compliance.

External Crowdsourcing or Pentesters
Outside Resources: This calls for the employment of outside pentesting resources, either from a crowdsourcing security service provider or from outside pentesting specialists.
Absence of Consistency and Standardization The usage of pentesting tools in this methodology will not be standardized or consistent, which frequently leads to inconsistent outcomes when gauging progress.
Cost Increase: Due to consulting fees and the requirement for specialized services, external pentesters may be more costly.
Restricted Frequency: Instead of being done continually, external pentesting is usually done on a periodic basis, leaving intervals between tests.

When to utilize it: Results from internal pentesting can be validated with the help of external pentesters or crowdsourcing. Still, there are issues with the results’ lack of uniformity and consistency.

Which Penetration Testing Methodology Is Best?

Penetration testing services are delivered in three main ways. Experts may advise you on the best approach to accomplish the goals of the company based on your needs, the kind of assets being tested, and which strategy will produce the desired results.

Black Box: No prior knowledge of the targeted systems under test is necessary for this kind of penetration testing. Without knowing any inside details about the compromised system, pentesting professionals will simulate a real-world attack that an attacker may employ. Evaluating the effectiveness of security measures and their resilience to external attacks is the aim.

Gray Box: This pentesting technique keeps some information about the target system or systems. Compared to Black Box, more context is offered, enabling a more effective assessment of the item or assets being exploited. The internal viewpoint of a White Box test and the exterior viewpoint of a Black Box test can be balanced by Gray Box testing.

White Box: This kind of testing necessitates thorough understanding of the targets, including both internal and external systems. This technique simulates an assault by an insider with in-depth knowledge of the system or systems. White box testing enables a thorough evaluation of internal controls to find weaknesses that might not be immediately apparent from the outside.

The Significance of Standardization in Pentesting

To guarantee accuracy, consistency, completeness, and adherence to industry standards, penetration testing frequently employs a number of significant defined rules. The following are a few of the more typical methods:

1. National Institute of Standards and Technology, or NIST

These guidelines offer helpful suggestions for creating, putting into practice, and maintaining security procedures and testing. It is intended to assist businesses, governments, and organizations in lowering cybersecurity threats. It covers a number of security testing topics, such as risk assessments, vulnerability scanning, and penetration testing. To guarantee a uniform approach to security testing, federal agencies and organizations follow and obey NIST principles.