As security technology and threat awareness among organizations improves so do the adversaries who are adopting and relying on new techniques to maximize speed and impact while evading detection.
Ransomware and malware continue to be the method of choice by big game hunting (BGH) cyber criminals, and the increased use of hands-on or “interactive intrusion” techniques is particularly concerning. Unlike malware attacks that rely on automated malicious tools and scripts, human-driven intrusions use the creativity and problem-solving abilities of attackers. These individuals can imitate normal user or administrative behaviors, making it difficult to differentiate between legitimate activities and cyber-attacks.
The main aim of most security practitioners today is to handle risk at scale. Enhancing visibility, minimizing noise, and safeguarding the attack surface across the enterprise demands the appropriate individuals, procedures, and security solutions.
By employing penetration testing services, organizations can actively counter these new and evolving threats aiding security practitioners in recognizing and validating what is routine and what is potentially malicious activity. Penetration testing involves diverse technologies, both human-led and automated, and the utilization of certified pentesting experts, or ethical hackers, to simulate a cyber-attack against a network and its asset(s). Pentesters will utilize real-world strategies and procedures similar to those of intruders with the objective of identifying and exploiting a known or unknown vulnerability before a breach occurs.
This form of proactive offensive security strategy necessitates planning and preparation by security leaders to enhance the effectiveness of penetration testing, including selecting the appropriate security provider to align with your security and business goals.
Guidelines for Successful Penetration Testing
The subsequent guidelines are essential to adequately prepare and organize for penetration testing, all of which will be elaborated further:
- Create team: Determine the security leaders involved in the penetration testing endeavor, including establishing a primary POC or central coordinator. Define roles and responsibilities and establish precise goals.
- Interested parties: Identify the vital stakeholders and decision-makers. What are their functions and when will their authorizations be required and at what phase of the penetration testing.
- Develop a project scheme: Ensure that a comprehensive project plan is prepared outlining the testing scope, specific systems and assets for testing, timeline, objectives, and anticipated outcomes.
- Select a testing methodology: Choose the right testing methodology to suit the scope. Common methodologies include Black Box, White Box, and Gray Box testing. Also, consider the specific tactics your organization wishes to implement whether it is social engineering, API Fuzzing, external-facing web app testing, etc.
- Assistance for the security team: Deliberate on the support the security team will require and ascertain if the organization possesses the appropriate expertise, resources, and budget. Determine whether the project will be managed internally or if an external pentesting service provider is necessary. If opting for an external service provider, inquire about the type of support and expertise they provide.
- Interaction with the vendor: Following some investigation, ensure to pose relevant inquiries when selecting a vendor. Queries may encompass, but are not restricted to:
- Is penetration testing an integral part of your core business?
- Are you covered by professional liability insurance?
- Can you furnish references or testimonials?
- Do you possess the appropriate pentesting certifications such as ISO 9001 or CREST?
- What are the qualifications of your pentesters?
- How do you remain up-to-date with the latest vulnerabilities and exploits?
- What is your pentesting methodology and pricing structures?
- Retrospective of Audit: Creating a comprehensive report of the pentesting discoveries and suggestions for remediation will be essential. Analyze the findings and potential risks associated with them with your team, and pentesting service provider if utilized. Collaborate closely with stakeholders to guarantee a complete understanding of the results and establish an agreed-upon timeline for timely remediation.
- Proactive steps for remediation: Formulate a report detailing findings intricately and offer clear instructions on the prioritization of vulnerabilities based on severity, identifying proactive steps to mitigate these risks. Maintain efficient communication, responsibility, and swift resolution.
- Recheck and confirm: Additional retesting may be necessary to confirm the efficacy of the remediation efforts and that they have been addressed successfully. Ensure that no new issues have surfaced during the pentesting process.
Getting Ready for Penetration Testing Services
Comprehend Your Attack Surface
To grasp your attack surface, it is crucial to possess complete visibility of your cyber assets. There are three primary considerations to understanding your attack surface:
1. Insight into Your Attack Surface: Spot hidden and unregulated cyber assets
Attackers are progressively leveraging the attack surface as an organization’s digital presence expands. This extended attack surface simplifies the discovery of vulnerabilities for malicious actors while complicating the protection of their IT ecosystem for security practitioners. Identifying all cyber assets and potential vulnerabilities can pose a significant challenge. Without full visibility into every potential attack vector, assessing and conveying an organization’s exposure to risk becomes nearly unfeasible.
2. Prioritization of Risk: Formulating decisions based on risk
Monitoring and evaluating risk without ongoing assessments expose organizations to vulnerabilities. Security leaders necessitate clear insight into the predominant factors affecting risk to guide strategic decisions and maintain stakeholders informed. Through regular risk assessments, DevSecOps teams garner actionable insights that help fortify defenses, rectify vulnerabilities, and avert security breaches.
3. Minimizing Risk: Curbing attack surface risk
Security practitioners frequently find themselves reacting to threats, impeded by restricted time and visibility, and lacking the counsel necessary to predict risks. A vast attack surface mandates more than optimizing threat defense – it demands proactive measures to identify, evaluate, and counteract cyber risk before an attacker commences an assault.
Determine the
When considering the extent of a penetration test, keep these points in mind prior to commencing the assessment:
1. Determine What to Investigate: Which aspects and resources does the enterprise wish to analyze? This entails pinpointing critical systems, applications, networks, or data that might be susceptible to breaches.
2. Define Objectives: Security teams should also take into account the business aims of the penetration test, whether it involves focusing on human security proficiency via phishing tactics, or examining endpoints that are susceptible to bypassing. It’s crucial to comprehend where there could be potential vulnerabilities in specific areas or to evaluate the entire system.
3. Adherence Obligations: Certain sectors have particular standards that might determine what should be covered in your penetration test. Understanding which regulations the enterprise must adhere to along with the testing prerequisites can assist in narrowing down the scope of the assessment.
Security experts should be equipped with this knowledge along with essential particulars such as organizational framework, domains, servers, devices with IP addresses, or authorized user logins (based on the penetration testing technique), and any exclusions.
Common Resources for Evaluation
Outer Resources
Web Platforms: The prevalent external resource(s) that benefit from penetration testing services are web platforms. External web application penetration testing detects feasible attack routes and addresses specific vulnerabilities depending on the architecture and technology employed by the applications. These are often referred to as internet- or publicly-accessible applications that are reachable over the web. The typical vulnerabilities identified include SQL injections, XSS, authentication and/or business logic weaknesses, credential stuffing, and others.
Furthermore, penetration testing services for external resources can encompass, among other things, mobile applications, APIs, Cloud, external networks, IoT, and meticulous code inspection.
Internal Resources
Networking Infrastructure: The most recurrent form of penetration testing for internal resources involves internal networks and systems. Although many security professionals and businesses assume that internal networks are more secure compared to outward-facing systems, this is no longer the case. The objective of intruders who manage to breach an internal network is to traverse across systems laterally, elevate privileges, and compromise confidential and sensitive information. The prevalent vulnerabilities found encompass misconfigured active directories (ADs), feeble passwords or inadequate authentication, and obsolete or unpatched software and systems.
Penetration testing services for internal resources can involve, but are not restricted to, internal applications, APIs and API endpoints, workstations and laptops, Thick Client applications, and evaluation throughout all stages of the software development life cycle (SDLC).
Choosing the Appropriate Penetration Testing Method
There are various penetration testing methodologies available, and selecting the appropriate one is dictated by the specifications outlined in your scope. Penetration testing methodologies have progressed, freeing companies from the traditional penetration testing offered by prominent consulting firms. Below are the assorted pentesting methods accessible and their common applications to deliver optimal outcomes.
1. Conventional Pentesting: This project-oriented and conventional format is provided by large global consulting corporations. This type of pentesting is hands-on and involves a specified scope and timeframe, where external security specialists conduct assessments on distinct systems, networks, or applications. Although this traditional pentesting can seem more authentic by delivering reassurance to stakeholders and auditors, it can often be quite expensive as these organizations typically levy a premium for their services, making it less cost-effective for small or medium-sized enterprises.
Traditional pentesting typically occurs annually or biannually, leaving gaps in security visibility between assessments. Given that the attack surfaces evolve rapidly, new vulnerabilities may remain undetected during this interval.
Moreover, these customary engagements usually have extended initiation periods, and the feedback loops may seem tardy. Results could take weeks or months to be communicated, by which time some vulnerabilities might have become irrelevant.
2. Self-Governing Pentesting: Automated penetration testing employs automated tools, scripts, and AI to conduct security reviews without continuous human input. Similar to other pentesting methodologies, it can replicate a range of attack scenarios, identify vulnerabilities, and suggest remedial actions. Automated pentesting is capable of executing the same tasks that manual testing would require, although it is carried out on a recurring or scheduled basis.
Automated penetration testing predominantly concentrates on networks and network services, efficiently scanning extensive network infrastructures. This form of pentesting can also conduct static and dynamic assessments of web applications to locate common vulnerabilities, in addition to APIs and API endpoints, cloud and external-facing resources such as public websites, databases, and networks, since it can be frequently scheduled and is less susceptible to human errors.
Automated pentesting provides swiftness, scalability, and cost-effectiveness. Autonomous tools can be deployed for regular pen tests, delivering continual monitoring and enabling the identification of vulnerabilities as they surface. However, automated tools tend to focus on common, well-known vulnerabilities and may fail to uncover intricate or more advanced weaknesses that a human tester could discern.
3. Penetration Testing as a Managed Service (PTaaS): PTaaS is a fusion or a hybrid melding of autonomous and human-guided pentesting, reaping benefits from both facets such as expediency, scale, and repetition. Manual pentesting is conducted by certified and highly adept ethical hackers who scrutinize a system, application, or network for vulnerabilities. It embodies a profound, human-centered strategy, and unlike automated tools, manual pentesting provides more expertise, intuition, and adaptability in uncovering complex vulnerabilities.
PTaaS encompasses the entire IT framework, both internal and external, and can be personalized for deeper exploration of particular areas of concern. During manual pentesting, professionals can think akin to attackers, utilizing methods like those employed by malevolent entities, and tailor specific usage scenarios or rare configurations for testing to harmonize with the organization’s IT ecosystem. Manual testers can also adjust their approach when faced with unforeseen situations or defenses.
Adopting a hybrid model for penetration testing combines the efficiency, scalability, and cost-effectiveness of continual automated testing with the ingenuity and adaptability of manual testing, crucial for unveiling complex and sophisticated vulnerabilities such as business logic flaws. Blending both methodologies ensures the speed and breadth of automated tools coupled with the depth of manual testers to ensure more comprehensive and exhaustive coverage of the attack surface.
Preparation for Your Penetration Testing
Selecting Suitable Pentesting Services and Vendor
Picking between internal and external pentesting resources is a critical choice, often dictated by the scope and goals. Distinguishing between an organization’s internal pentesting team,an external penetration testing provider that employs their own internal penetration testing specialists, as well as external resources like crowdsourcing, each possess their distinct pros and cons.
Internal Breach Testing within Organizations
- Insider Viewpoint: Emulates an attack originating from within the organization, offering an insider’s viewpoint.
- Internal Infrastructure: Is capable of delivering a comprehensive evaluation of internal systems, covering lateral movement and privilege escalation.
- Cost-efficiency: With expertise and resources retained within the organization, penetration testing can often be economically viable, reducing the necessity for unnecessary external expenses.
- Continuous Enhancement: Internal teams can conduct ongoing testing and monitoring leading to more regular updates and enhancements.
When to utilize: Internal breach testing is most suitable for uncovering and mitigating internal threats, assessing internal protocols, and ensuring the security of internal systems.
External Penetration Testing with Service Provider and In-house Certified Specialists
- Specialized Proficiency: In-house penetration testing specialists hired by a penetration testing service provider are extensively trained certified ethical hackers and uphold the most current industry certifications such as CREST, OSCP, OSCE, CEH, CISA, CISM, SANS, and others.
- Impartial Outlook: External pentesters can supply an impartial viewpoint, often uncovering vulnerabilities that internal teams might overlook.
- Uniformity: Adheres to standardized practices and guidelines aligning with NIST, OWASP, CREST, and MITRE ATT&CK methodologies.
- Assistance and Tailoring: Penetration testing providers also extend the necessary guidance to select the appropriate penetration testing technique, providing assistance throughout the entire testing process, with the capability to customize and adapt security testing to match your business requirements.
When to utilize: External penetration testing is most suitable when resources and expertise are limited. It is advantageous for evaluating both internal and external-facing assets using standardized methodologies for more precise and consistent outcomes. Additionally, it is preferable for ensuring regulatory compliance and obtaining an impartial evaluation of your security stance.
External Penetration Testers or Crowdsourcing
- External Resources: This entails external penetration testing resources either through a security service provider that employs crowdsourcing or the deployment of external penetration testing specialists.
- Deficiency in Standardization and Uniformity: This method will lack standardization and consistency in the use of penetration testing tools, resulting in varied results that hinder progress measurement.
- Augmented Expense: External pentesters can be pricier due to consultancy charges and the requirement for specialized services.
- Restricted Frequency: External penetration testing is usually carried out periodically, rather than continuously, creating intervals between testing.
When to utilize: External penetration testers or crowdsourcing are beneficial for validating results from internal penetration testing for validation. Nonetheless, the absence of standardization and consistency in results remains a concern.
Which Penetration Testing Methodology is Appropriate?
There are three main approaches used to provide penetration testing services. Depending on your needs, the types of assets being tested, and which approach will yield the desired outcomes, experts can advise you on the most suitable method to achieve the organization’s objectives.
Black Box: This form of penetration testing necessitates no prior knowledge regarding the targeted systems being tested. Pentesting experts will imitate a real-world attack that a malefactor might employ without internal information about the system being compromised. The objective is to evaluate the effectiveness of security measures and whether these controls can withstand an external attack.
Gray Box: This penetration testing method retains partial knowledge of the target system(s). More context is provided than Black Box, enabling a more efficient evaluation of the asset(s) being exploited. Gray Box testing can strike a balance between the external perspective of Black Box and the internal perspective of White Box tests.
White Box: Comprehensive knowledge of targets is imperative for this testing type, encompassing internal and external systems. This method replicates an attack conducted by an insider within the organization or someone with intricate knowledge of the system(s). White Box testing facilitates a thorough evaluation of the internal controls to unearth vulnerabilities that may not be immediately apparent from an external perspective.
Why Uniformity Holds Significance in Penetration Testing
Several crucial standardized guidelines are commonly employed in penetration testing to ensure precision, consistency, thoroughness, and alignment with industry practices. Here are some of the more prevalent practices:
1. NIST (National Institute of Standards and Technology)
These guidelines provide pragmatic recommendations for crafting, implementing, and upholding security testing and processes. It caters to industry, government, and organizations to help mitigate cybersecurity risks. It encompasses assorted aspects of security testing, inclusive of penetration testing, vulnerability scanning, risk assessments. NIST guidelines are widely esteemed and utilized by federal agencies and organizations to guarantee a standardized approach to security testing.
2. OWASP (Open Web Application Security Project)
OWASP furnishes a comprehensive framework for testing web applications, encompassing methodologies for identifying and mitigating prevalent web application vulnerabilities. OWASP is highly regarded for its emphasis on web applications – but extends to frameworks for mobile apps, APIs, cloud, and more – while its guidelines are open-source and regularly updated to reflect the latest threats and best practices.
3. CREST (Council of Registered Ethical Security Testers)
A nonprofit accreditation body that establishes high standards for security testing, including penetration testing, to ensure member organizations adhere to rigorous ethical, legal, and technical standards. CREST delineates a standardized methodology for penetration testing, covering planning, information gathering, vulnerability analysis, exploitation, and reporting.
Other Noteworthy Guidelines:
- MITRE ATT&CK: A global repository of adversary tactics and techniques derived from real-world observations utilized to formulate specific threat models and methodologies in the private sector, government, and cyber community. Unlike traditional penetration testing frameworks, MITRE ATT&CK furnishes a comprehensive matrix of techniques employed by assailants during various stages of an attack.
- PCI DSS (Payment Card Industry Data Security Standard): Lays down requirements for conducting penetration tests to safeguard cardholder data.
- OSSTMM (Open-Source Security Testing Methodology Manual): Offers detailed approaches for security testing, encompassing various facets of operational security.
- HIPAA (Health Insurance Portability and Accountability Act): Encompasses guidelines for penetration testing to ensure the security of protected health information.
Regulatory Compliance via Penetration Testing
Adhering to regulatory directives has becomeAs stricter and more stringent rules are being rolled out globally, different sectors such as finance, healthcare, and critical infrastructure are facing the brunt. Here’s an overview of some notable regulations, many of which include specific guidelines related to penetration testing:
DORA: Threat-Led Pen Testing (TLPT)
To counter the escalating threats from internal and external information systems or IT infrastructure, EU regulators introduced regulations and recommendations for pinpointing and resolving potential vulnerabilities. Through DORA, financial institutions were mandated to undergo two types of unique testing to bolster their cyber resilience:
- Digital Operational Resilience Testing: Compulsory for all entities under DORA, conducted annually for systems and applications supporting critical functions,
- Threat-Led Pen Testing (TLPT): Required for major financial entities identified by competent authorities in each country, with TLPT conducted at least every three years.
NCSC Cyber Assessment Framework (CAF)
CAF is vital for public sector entities and those supporting Critical National Infrastructure (CNI), offering a systematic way to evaluate cybersecurity practices and pinpoint areas for enhancement. It’s particularly relevant for organizations under the Network and Information Systems (NIS) Regulations, which mandate the adoption of suitable cybersecurity measures. Additionally, the framework serves as a valuable asset for sectors managing risks to public safety, like healthcare and transportation.
NIS2 Directive
The NIS 2 Directive (Directive (EU) 2022/2555) aims to establish a high level of cybersecurity across the EU. Member States must ensure that essential entities implement appropriate measures to handle network and information system risks, reducing incident impacts using a comprehensive approach.
TIBER-EU (Threat Intelligence-Based Ethical Red Teaming)
This EU initiative is crafted to boost the cyber resilience of financial sector entities. TIBER-EU presents a methodical approach for executing controlled, intelligence-driven red team tests. These tests mimic real cyberattacks to evaluate and enhance the security stance of organizations.
SOC 2 (System and Organization Controls 2)
A recognized regulatory framework and audit processes developed by the American Institute of Certified Public Accountants (AICPA), focusing on evaluating controls and security measures for service organizations to safeguard customer data and ensure data security, availability, processing integrity, confidentiality, and privacy.
HIPAA (Health Insurance Portability and Accountability Act)
This US federal law regulates the privacy, safety, and electronic exchange of medical information. Healthcare organizations must conduct regular security control validations of their data security, including penetration testing guidelines to safeguard protected health information.
PCI DSS (Payment Card Industry Data Security Standard)
Lays down requirements for penetration tests to secure cardholder data. PCI DSS 11.3.1 mandates external penetration testing at least every six months and after significant IT infrastructure or application changes. PCI DSS 11.3.2 requires internal pentesting every six months. More details on additional requirements are available on their website.
To Sum Up
Preparing for and organizing penetration testing services is a substantial task, with numerous questions to address and preparations to make before commencement. Nonetheless, the advantages of penetration testing services undoubtedly justify the effort to uphold a robust security position both now and in the future.
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