Infrastructure Landscape

Generic ICT Environments

This term refers broadly to the technology enabling digital communication between servers and clients over a network, encompassing software, hardware, and middleware. It is distinct from cloud environments and is often used for IT operations.


Cloud Environment

Cloud computing allows on-demand delivery of IT resources over the internet, managed by cloud service providers (CSPs). It includes different service models like Infrastructure as a Service (IaaS), Platform as a Service (PaaS), and Software as a Service (SaaS). Penetration testing in the cloud requires understanding the shared responsibility model, dynamic environments, multi-tenancy, and security of APIs and configurations.


IoT Infrastructures

IoT (Internet of Things) involves interconnected devices that collect and process data. It is divided into Consumer IoT (CIoT) and Industrial IoT (IIoT). Key components of IoT infrastructures include IoT devices, data processing capabilities, and connectivity technologies. Penetration testing in IoT environments must address device heterogeneity, communication protocols, firmware security, and data security among other challenges.


Operational Technology (OT)/Industrial Control Systems (ICS)

OT encompasses the hardware and software used to monitor and control physical processes in industries. Penetration testing in OT environments requires careful planning to avoid disruption, understanding unique communication protocols, and ensuring regulatory compliance.


Cyber-Physical Systems (CPS)

CPS are systems that integrate computational and physical components, requiring real-time processing and interaction with the physical world. They pose significant challenges in terms of design, security, and reliability, especially as they are prime targets for cyber-attacks.


Overall, this chapter emphasizes the importance of tailored penetration testing approaches for different infrastructure types to ensure security and effective risk management in modern digital ecosystems.

Strategies for Security Vulnerability Discovery

various methods for discovering security vulnerabilities, their goals, benefits, and how they can work together to form a comprehensive cybersecurity strategy.

Whiteboard Hacking – Threat Modelling

A collaborative process analyzing potential threats through diagrams, identifying attack vectors, weaknesses, and vulnerabilities. It operates at multiple levels of abstraction, including enterprise, system, application, network, data, component, and user levels.


Vulnerability Scanning:

A technique to quickly gather vulnerabilities using specialized tools. It plays a crucial role in assessing an organization’s security posture and can be performed automatically at regular intervals. Different types of scans include network, host-based, application, database, wireless, cloud, and compliance scans.


Responsible Disclosure

Involves implementing a Vulnerability Responsible Disclosure Policy (VDP) to allow individuals to report vulnerabilities without fear of legal repercussions. This approach expands opportunities for discovering vulnerabilities.


Penetration Testing

Simulates real-world cyberattacks to identify vulnerabilities that automated tools might miss. It provides actionable intelligence for improving security measures.


Bug Bounty Hunting

Involves individuals reporting vulnerabilities for rewards, incentivizing the discovery of issues before they can be exploited.


Red Teaming

A simulated adversarial practice to assess an organization’s security posture by emulating real-world attacks. It tests various security aspects, including access control, data protection, physical security, and operational resilience.


The Role of Penetration Testing in a Comprehensive Vulnerability Discovery Strategy

Penetration testing is highlighted as a crucial element of a broader vulnerability discovery strategy. It helps simulate real-world attacks and assess the effectiveness of security measures. Key points include

Comprehensive Assessment: Penetration testing provides a practical assessment of security posture, uncovering hidden vulnerabilities that automated tools might miss.

Prioritization of Risks: It helps organizations prioritize risks based on the potential impact of vulnerabilities.’

Regulatory Compliance: Assists in meeting compliance requirements by providing necessary documentation.

Continuous Improvement: Regular penetration testing enhances the security posture and prepares organizations for evolving threats.

How to organize and carry out penetration tests, detailing each stage of the process and how they apply across different technology environments, such as traditional IT, Cloud, Operational Technology (OT), and Cyber-Physical Systems (CPS). The importance of penetration testing in identifying and exploiting vulnerabilities in a controlled setting is emphasized, helping organizations understand security gaps and proactively enhance their security measures.

Management of the Penetration Testing Portfolio

This layer involves strategic oversight and coordination of all penetration testing activities across the organization. Key phases include:

Strategic Alignment: Ensuring the portfolio aligns with organizational goals and security objectives.

Planning and Prioritization: Deciding which systems require testing based on risk assessments and business priorities.

Budgeting and Resource Allocation: Determining the necessary financial and human resources for conducting tests.

Execution and Monitoring: Overseeing individual tests to ensure they stay within scope and recommendations are evaluated.

Tracking and Reporting: Maintaining an overview of all penetration testing activities and assessing the effectiveness of remediation efforts.

Review and Improvement Reporting: Regularly reviewing progress and adjusting the portfolio based on new risks or changes.


Process of Conducting a Specific Penetration Test

Pre-engagement and Scoping: Establishing clear objectives and defining the scope of the test.

Reconnaissance and Information Gathering: Collecting data about the target system using passive and active methods.

Scanning – Vulnerability Identification: Analyzing systems to uncover specific weaknesses using network scanning and vulnerability scanning techniques.

Exploitation: Validating the impact of identified vulnerabilities by exploiting them in a controlled environment.

Post-Exploitation: Assessing the broader impact of successfully exploited vulnerabilities and evaluating potential consequences.

Report on Findings and Remediations: Preparing a detailed report summarizing findings, actionable remediation steps, and conducting a debriefing with stakeholders.

Remediation and Follow-Up: Addressing identified vulnerabilities and conducting follow-up tests to ensure effective mitigation.


Types of Penetration Tests

Penetration testing encompasses various approaches targeting different aspects of an organization’s security posture. Key types of tests include:

Network and Wi-Fi Testing:

This involves both external and internal penetration tests, including wireless networks, to address unique vulnerabilities.

Web Application and API Testing:

Assessing both client-side and server-side components of web applications for common vulnerabilities like SQL injection and cross-site scripting.

Mobile Penetration Testing:

Checking for issues specific to mobile environments, such as insecure data storage and improper handling of sensitive information.

Cloud Security Testing:

Ensuring cloud services are configured securely, examining access controls, encryption practices, and overall architecture.

These various methods contribute to a comprehensive security assessment by identifying potential weaknesses across different systems and environments.

This page was created using insights from the report CYSSDE D2.1 Methodologies Pentesting

To read the full report, please use the link below.