What is a Pentest?

Penetration testing, or pen testing, involves authorised simulations of attacks on an organisation’s network or applications to pinpoint vulnerabilities and security concerns. The discovered vulnerabilities are exploited to confirm their severity and compromise machines. Machines or applications compromised in the process are utilized to access an organisation’s network, aiding in the assessment of potential attacker access levels.

Penetration Testing Overview: How The Process Works

A typical penetration test involves several stages:

1. Planning and Scope Definition: Define the goals, scope, and rules of engagement for the test. Determine the systems, networks, and applications to be tested, as well as the testing methods and timeframe.
2. Reconnaissance: Gather information about the target, such as IP addresses, domain names, and network infrastructure. This phase may involve both passive (information available publicly) and active (network scanning) reconnaissance.
3. Vulnerability Analysis: Identify and assess potential vulnerabilities in the target systems. This may include scanning for open ports, services, and known vulnerabilities.
4. Exploitation: Attempt to exploit identified vulnerabilities to gain unauthorised access. This step helps confirm the severity of the vulnerabilities and their potential impact.
5. Post-Exploitation: Once access is gained, assess the extent of the compromise and identify what an attacker could achieve with the access.
6. Documentation: Document all findings, including vulnerabilities, exploits used, and recommendations for remediation. This documentation provides a comprehensive report for the organisation.
7. Reporting: Present the findings to the organisation’s stakeholders, including technical details, risk assessments, and recommendations for improving security.

It is important to note that penetration tests should be conducted by skilled and ethical professionals, and organisations should be aware of and approve the testing activities to prevent unnecessary disruptions. The goal is to provide valuable insights into security weaknesses and help organisations enhance their overall cybersecurity posture.

Who Performs Penetration Testing

Penetration tests are typically conducted by external third party penetration testing companies by cybersecurity professionals, often referred to as ethical hackers or penetration testers. External third party security testing companies have expertise in identifying and exploiting vulnerabilities in systems, networks, and applications. They are hired by organisations to assess the security of their infrastructure and provide insights into potential weaknesses that malicious actors could exploit.

Penetration Testing Types

There are various types of penetration tests, each focusing on specific aspects of a system’s security. Some common types include:

• Black Box Testing: Testers have little or no prior knowledge of the system, simulating an external hacker’s perspective.
• White Box Testing: Testers have full knowledge of the system, including source code and architecture, simulating an insider’s perspective.
• Grey Box Testing: Testers have partial knowledge of the system, combining elements of both black and white box testing.
• External Testing: Assessing the security of externally-facing systems, such as websites and servers.
• Internal Testing: Simulating an attack from within the organization to identify vulnerabilities that could be exploited by insiders.
• Web App Security Testing: Focusing specifically on the security of web applications to uncover vulnerabilities like SQL injection or cross-site scripting.
• Network Penetration Testing: Evaluating the security of network infrastructure, identifying weaknesses in routers, switches, and other network devices.
• Social Engineering Testing: Assessing human behavior and susceptibility to manipulation, often involving tactics like phishing.
• Mobile App Security Testing: Evaluating the security of mobile apps to identify vulnerabilities and potential exploits.

The choice of which type of penetration test to perform depends on the specific goals and requirements of the organisation.

A penetration test could offer an understanding of an organisation’s security posture by revealing the following information:

1. Vulnerabilities: Identify and assess vulnerabilities in systems, networks, and applications.
2. Exploitation Potential: Determine the extent to which identified vulnerabilities can be exploited to gain unauthorised access.
3. Weaknesses in Policies and Procedures: Evaluate the effectiveness of security policies and procedures in place, including incident response and user awareness training.
4. Impact Assessment: Assess the potential impact of a successful cyber attack on the organisation’s operations, data, and reputation.
5. Scope of Compromise: Identify how far an attacker could potentially penetrate the network or systems, including lateral movement within the infrastructure.
6. Security Controls Effectiveness: Evaluate the effectiveness of existing security controls, such as firewalls, intrusion detection systems, and antivirus solutions.
7. Incident Response: Test the organisation’s ability to detect and respond to a simulated cyber attack, assessing the effectiveness of the incident response plan.
8. User Awareness: Assess the susceptibility of employees to social engineering attacks, such as phishing.
9. Compliance Adherence: Determine if the organisation complies with relevant regulatory requirements and industry standards.
10. Recommendations for Improvement: Provide actionable recommendations to address identified vulnerabilities and weaknesses, improving the overall security posture.

The ultimate goal of a penetration test is to empower the organisation with insights that help enhance its cybersecurity defences, mitigate risks, and prevent potential security incidents.

What Happens After a Penetration Test:

1. Reporting and Documentation: The penetration testing team compiles a detailed report outlining the findings, including identified vulnerabilities, exploits used, and the overall assessment of the organisation’s security posture.
2. Debriefing: A debriefing session may occur with key stakeholders to discuss the results, clarify any questions, and ensure a mutual understanding of the findings.
3. Prioritisation of Remediation: The organisation prioritises the identified vulnerabilities based on their severity and potential impact. Critical issues are addressed first to enhance security rapidly.
4. Remediation Actions: The IT and security teams implement measures to address and fix the identified vulnerabilities. This may involve patching systems, updating software, or adjusting configurations.
5. Retesting: In some cases, the organisation may opt for a follow-up penetration test to validate that the remediation efforts have effectively addressed the identified vulnerabilities. This helps ensure that the security improvements are successful.
6. Documentation of Changes: Any changes made to the systems or network configurations in response to the penetration test findings are documented for future reference and audits.
7. Continuous Improvement: Organisations use the insights gained from the penetration test to improve their overall security posture. This may involve refining security policies, enhancing employee training, or investing in additional security technologies.
8. Training and Awareness: Employees may receive additional training and awareness programs based on the social engineering aspects revealed during the test, aiming to reduce the risk of falling victim to such attacks.
9. Compliance Updates: If the penetration test was conducted to assess compliance with regulatory requirements or industry standards, the organisation ensures that any necessary adjustments are made to align with the relevant guidelines.
10. Feedback Loop: Establishing a feedback loop is essential to continuously improve the security strategy. Insights gained from the penetration test inform ongoing security measures and may influence future testing strategies.

Effective Use of Penetration Testing

Penetration testing is a vital element in bolstering an organisation’s cybersecurity defences. To employ it effectively, the initial step involves defining clear objectives. This entails outlining specific goals and objectives for the penetration test, providing a comprehensive understanding of the aspects within the organisation’s security framework that require assessment. Once these objectives are established, the next crucial step is to clearly define the scope of the penetration test. This involves specifying the systems, networks, and applications that will undergo testing, facilitating a focused and resource-optimised assessment.

Engaging skilled professionals is paramount for a successful penetration testing process. Ethical hackers or penetration testers with expertise in diverse areas, including network security, web applications, and social engineering, contribute their knowledge and experience to conduct a thorough and insightful assessment. Simulating realistic scenarios that mimic potential real world cyber threats is also a key component. This approach provides practical insights into vulnerabilities and weaknesses, offering valuable information for remediation. Regular penetration testing, a combination of automated and manual testing methods, comprehensive reporting, prioritised remediation, continuous improvement, and compliance considerations further contribute to a holistic and effective use of penetration testing, ensuring that an organisation’s security remains resilient and adaptive in the face of evolving cyber threats.

What Sort of Systems Need Penetration Testing?

1. Network Infrastructure: Assess the security of routers, switches, firewalls, and other network devices to identify vulnerabilities that could be exploited.
2. Web Applications: Test the security of web applications for vulnerabilities such as SQL injection, cross-site scripting (XSS), and insecure direct object references (IDOR).
3. Databases: Evaluate the security of databases to ensure that sensitive data is protected and assess for any vulnerabilities that could lead to unauthorised access.
4. Operating Systems: Test the security of servers and endpoints, including both Windows and Linux systems, to identify vulnerabilities and potential entry points for attackers.
5. Wireless Networks: Assess the security of Wi-Fi networks to identify weaknesses and potential points of unauthorised access.
6. Cloud Services: Evaluate the security of cloud-based services and infrastructure to ensure that configurations are secure and data is adequately protected.
7. Mobile Applications: Test the security of mobile apps to identify vulnerabilities and weaknesses that could be exploited by attackers.
8. Social Engineering: Assess the susceptibility of employees to social engineering attacks, including phishing, to evaluate the effectiveness of security awareness training.
9. Physical Security: In some cases, physical security measures may be tested to identify potential weaknesses in access controls, surveillance, and other physical security measures.
10. IoT Devices: If applicable, test the security of Internet of Things (IoT) devices to identify vulnerabilities and potential risks associated with these connected devices.

It’s important to tailor the penetration testing approach to the specific needs and environment of the organisation. A thorough testing strategy considers all relevant systems and potential entry points to provide a comprehensive assessment of the overall security posture.

What is Manual Pentesting?

Manual pen testing leverages the best in class security auditing software and tools and uses human expertise to combine the best of both options and rule out any false positives in the final report. Automated software solutions are unable to identify specific logic flaws and manual Pentesting is required to identify issues based on technical experience. The process of combining both testing solutions is commonly referred to as Vulnerability Assessment and Penetration Testing (VAPT), see our what is VAPT resource for more information.

Aptive provide a consultant lead manual web app security audit service to help identify logic flaws and complex application security issues.

Penetration Testing Tools

1. Port Scanners:

   Definition: Port scanners are tools used to identify open and closed ports on a target system. They help penetration testers discover the network services running on specific ports, allowing for an understanding of potential entry points into the system.

   Example Tools:

   • Nmap: A powerful and versatile port scanner that can discover open ports, services, and perform version detection.
   • Masscan: A high-speed port scanner designed for large-scale network scans.
2. Vulnerability Scanners:

   Definition: Vulnerability scanners are tools that automate the process of identifying security vulnerabilities in a system or network. They assess weaknesses that could be exploited by attackers.

   Example Tools:

   • Nessus: A widely-used vulnerability scanner that provides in-depth analysis and reporting on identified vulnerabilities.
   • OpenVAS: An open-source vulnerability assessment tool that detects and reports security issues.
3. Web Application Scanners:

   Definition: Web application scanners focus on identifying vulnerabilities specific to web applications. They analyze web app components, including forms, inputs, and URLs, to uncover potential security flaws.

   Example Tools:

   • OWASP ZAP (Zed Attack Proxy): An open-source security tool designed for finding vulnerabilities in web applications during development and testing.
   • Burp Suite: A comprehensive platform for web application security testing, offering features like crawling and scanning.
4. Network Scanners:

   Definition: Network scanners explore and analyze the devices and hosts within a network. They provide insights into the network’s structure, connected devices, and potential security risks.

   Example Tools:

   • Wireshark: A widely-used network protocol analyzer for capturing and analyzing packets, offering deep insights into network traffic.
   • Angry IP Scanner: A fast and straightforward IP address and port scanner suitable for network reconnaissance.
5. Exploitation Tools:

   Definition: Exploitation tools are used to test and exploit identified vulnerabilities, gaining unauthorized access to systems. They simulate real-world attacks to assess the impact of vulnerabilities.

   Example Tools:

   • Metasploit: A penetration testing framework that allows testers to develop, test, and execute exploits against target systems.
   • ExploitDB: A comprehensive database of known exploits and their corresponding code.

These tools play crucial roles in a penetration tester’s toolkit, providing the necessary capabilities to identify, assess, and exploit security vulnerabilities.

Pentest FAQ

How Much Does a Pentest Cost?

This depends on the size and complexity of what requires assessment, contact us for an estimate or read more on our penetration testing services page.

Pentest vs Vulnerability Assessment?

A pentest is performed manually by a security professional, a vulnerability assessment is an automated assessment conducted by software.

What is the Purpose of Pentesting?

A Pentest, assess the security of IT infrastructure, API’s or web / mobile applications by attempting to exploit discovered vulnerabilities in a controlled way. These vulnerabilities are then documented, allowing an organisation to see an overview of the discovered issues and their associated risks, perform remediation of the issues, and then have the discovered issues reassessed to verify the remediation efforts were successful.

Learn about more about pen testing in our Cyber Security Section.