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Penetration Testing Frequently Asked Questions (FAQ)

We’ve compiled a list of 20 frequently asked questions (FAQs) about penetration testing. These questions cover a wide range of topics, from the basics of pen testing and its importance to specific types of tests and the skills required from testers. Whether you’re new to penetration testing or looking to deepen your understanding, these answers will give you the insights needed to enhance your organisation’s security measures.

1. What is Penetration Testing?
Penetration testing, or pen testing, is a controlled security assessment where ethical hackers or testers attempt to uncover vulnerabilities within a system, network, or application by following potential attack methods. Unlike real-world cyberattacks, pen testing is performed in a structured and authorised manner, aiming to identify weaknesses without causing actual harm. The process provides organisations with insights into their security gaps, allowing them to strengthen defences and reduce the risk of future exploits.
It helps organisations uncover security weaknesses, prevent data breaches, and maintain compliance with industry standards, protecting valuable systems and information.

Penetration testing can be categorised into several forms, each targeting different security aspects.  The most common testing types we deliver at Blackfoot are:

  • Network Penetration Testing: Focuses on finding vulnerabilities in network infrastructure, including routers, firewalls, and switches.
  • Application Testing: Identifies flaws in applications such as websites. Testing for injection attacks or authentication issues are common areas of focus.
  • Mobile Application Testing: Examines mobile apps for security gaps like improper encryption or data storage.
  • API Penetration Testing: Focuses on identifying vulnerabilities in APIs (Application Programming Interfaces), ensuring that data transmission between systems is secure.
  • IoT Penetration Testing: Analyses vulnerabilities in connected devices within an Internet of Things environment.
  • Social Engineering: Targets the human element, testing employee susceptibility to things like phishing and other aspects which are manipulative.
  • Cloud Testing: Evaluates the security of cloud-based systems and services, ensuring that cloud infrastructure and storage are properly configured and secure.
  • Wireless Network Testing: Identifies risks in wireless networks, including Wi-Fi, to detect weak encryption or unauthorised access points.
  • Physical Penetration Testing: Involves testing physical security measures, such as locks, access control, and security cameras, to see if an attacker could gain unauthorised physical access to sensitive areas.
  • Embedded Systems Penetration Testing: Targets systems with built-in software or hardware (e.g., medical devices, automotive systems) to identify risks in firmware or communication protocols.
Penetration testing frequency should be based on an organisation’s risk profile. High-risk environments, such as those handling sensitive data, may require more frequent testing to ensure vulnerabilities are promptly identified and then addressed. Additionally, testing should be considered when significant changes occur, such as new systems, software updates, or infrastructure modifications. This risk-based approach ensures that security defences are continuously evaluated, reducing the likelihood of undetected threats. Organisations should tailor testing schedules to reflect the complexity and criticality of their assets, ensuring they are adequately protected. Regulatory and compliance requirements may also need to be considered when deciding how often to test.  As general guidance, testing key systems at least annually and upon significant change is a reasonable baseline. 

Penetration testing is a comprehensive and manual process that evaluates an organization’s security by actively identifying and attempting to exploit vulnerabilities. Whereas vulnerability scanning relies on automated tools to identify known vulnerabilities in systems and applications. Both practices are critical for a comprehensive security strategy, they complement each other to provide a comprehensive view of an organisation’s security posture.  Security standards typically distinguish between penetration testing and vulnerability scanning as separate requirements due to the different advantages each provide.

Key differences include but are not limited to:

  1. Manual vs. Automated: Vulnerability scanning is automated, while penetration testing involves manual techniques and human judgment.
  2. Depth of Analysis: Penetration testing digs deeper into assessing the actual security posture, whereas vulnerability scanning focuses on identifying known vulnerabilities.
  3. Scope of Testing: Penetration tests often evaluate business logic and complex attack vectors that vulnerability scanners may miss.
  4. Chaining Vulnerabilities: Penetration testing can uncover opportunities for chaining vulnerabilities, exploiting multiple weaknesses in sequence to achieve a more significant compromise, whereas vulnerability scanning typically identifies individual vulnerabilities without assessing their potential to be exploited together often leading to false positives.
  5. Exploiting Vulnerabilities: Penetration testing involves actively exploiting vulnerabilities to demonstrate the risk they pose, which can lead to scenarios like unauthorised access or data exfiltration. In contrast, vulnerability scanning only detects potential issues without executing any exploit attempts, leaving it unknown as to whether a vulnerability is even exploitable.

Vulnerability Scanning

  • Purpose: To identify and report known vulnerabilities in systems, networks, or applications.
  • Process: Automated tools scan for common vulnerabilities, misconfigurations, and security issues based on a predefined database of known vulnerabilities (e.g., CVEs).
  • Frequency: Often performed regularly (e.g., daily, weekly, monthly) as part of ongoing security assessments.
  • Output: Provides an automated report generated by the scanner that lists identified vulnerabilities along with their severity and remediation recommendations.

Penetration Testing

  • Purpose: To assess the effectiveness of security controls and identify vulnerabilities that could be exploited by attackers.
  • Process: Conducted by highly skilled professionals (often referred to as ethical hackers or pen testers) who manually test systems using expert knowledge, tools and experience, attempting to exploit weaknesses often chaining vulnerabilities together to compromise systems.
  • Frequency: Typically conducted less frequently, often bi-annual or annually, or after significant change.
  • Output: Provides a detailed report that includes a description of the attacks performed, vulnerabilities exploited, sensitive data accessed, and very detailed and bespoke recommendations for remediation. Debrief calls with your tester also follow the report.

There are very minimal risks, such as potential service disruptions, experienced testers use safeguards to minimise any impact on business operations.

Depending on the scope, it can take a couple of days to several weeks or even months. Factors include the complexity of the systems being tested, the size of the environment and the depth of the test.

You receive a detailed report with findings, prioritised vulnerabilities, and actionable steps to mitigate them. It’s crucial to act on high-risk vulnerabilities and plan for remediation testing.  A debrief meeting with your Blackfoot tester is provided after every test.

Yes, you should still conduct a web application penetration test. While a WAF provides an important layer of security, it could still fail or be bypassed at times. Penetration testing will assess the security of the underlying application itself, helping to identify vulnerabilities that a WAF may not protect against. This comprehensive evaluation is essential for ensuring robust security.

One of the most common questions. The cost varies based on the type, scope, and complexity of the test. Pricing may range from a couple thousand pounds for a relatively small test to tens or hundreds of thousands for extensive testing of very large environments.

Testers use tools and techniques similar to those used by actual hackers, exploiting common vulnerabilities like weak passwords, unpatched software, and misconfigurations.

Internal testing focuses on systems that are accessible from within the organisation, while external testing targets public-facing systems typically exposed to the internet.

While some parts can be automated, manual testing is crucial to identify sophisticated vulnerabilities and weaknesses that automated tools can overlook.

Yes, several industry standards and regulatory frameworks, require or recommend regular penetration testing to protect sensitive data and systems.

Social engineering involves manipulating people into disclosing confidential information or performing actions that compromise security, often through phishing, impersonation, or other deceptive tactics used to obtain sensitive information.

Ensure all relevant stakeholders are informed, outline and agree the scope of the test, and provide the necessary access to the testers. Clarify any specific testing limitations or restrictions, set clear expectations and establish communication protocols for the duration of the test. It’s also important to ensure the testing team understands the environment and any operational considerations that may affect the test.

No, but it can significantly reduce risk by identifying and fixing system vulnerabilities before hackers find and exploit them. Cybersecurity is an ongoing process that must include regular testing, monitoring, and system updates.

Penetration testers should possess extensive knowledge of networking, programming, cybersecurity tools, and various hacking techniques. They are certified professionals, often holding credentials such as the Offensive Security Certified Professional (OSCP) or Certified Ethical Hacker (CEH). Engaging a CREST-accredited testing firm is highly recommended, along with The Cyber Scheme Certified Testers. Additionally, effective penetration testers should have strong problem-solving skills, an understanding of operating systems and applications, and the ability to think like an attacker, to identify and exploit vulnerabilities.

Red Team: The Red Team is responsible for simulating real-world attacks on an organisation. They employ sophisticated techniques, tools, and tactics to identify vulnerabilities and weaknesses covertly. Their primary goal is to breach security measures and gain unauthorised access to critical assets, mimicking the behaviour of actual adversaries. This approach helps organisations understand their security gaps and provides insights into how well their defences hold up against advanced threats.

Blue Team: The Blue Team represents the defensive side of cybersecurity. They are tasked with monitoring, detecting, and responding to security incidents in real time. This team works to strengthen the organisation’s security posture by implementing preventive measures, conducting threat analysis, and maintaining the integrity of systems and networks. The Blue Team’s effectiveness is crucial for identifying attacks, mitigating risks, and ensuring a swift response to security incidents.

Purple Team: The Purple Team acts as a bridge between the Red Team and Blue Team, facilitating communication and collaboration between the two. Their role is to enhance the overall security posture of the organisation by ensuring that the insights gained from Red Team activities are effectively communicated to the Blue Team. The Purple Team analyses the results of simulated attacks and helps the Blue Team understand the techniques used by the Red Team, enabling them to improve detection and response strategies. This collaboration fosters a culture of continuous improvement in security practices, allowing organisations to better prepare for and defend against actual attacks.

The amount of information you need to provide in advance of a penetration test largely depends on the agreed-upon approach:

  • Zero-Knowledge Testing (Black Box):
    Black box testing operates without any prior knowledge of the systems or applications the testers are tasked to evaluate. This approach simulates a real-world external attack scenario, where an attacker attempts to breach security without insider information. Testers must rely on their skills to discover vulnerabilities, test defences, and exploit weaknesses as an outsider would. This method assesses how well the organisation’s defences hold up against unanticipated threats and helps identify security gaps that could be exploited by malicious actors. The focus is on the external perimeter, assessing the effectiveness of firewalls, intrusion detection systems, and other protective measures in place. Black box testing can be more expensive due to more effort in establishing information and a lengthier process. 
  • Partial-Knowledge Testing (Gray Box):
    Grey box testing strikes a balance between black and white box. Testers are provided with limited information about the system, such as architecture diagrams, user roles, or access permissions. This can mimics the perspective of an insider threat or an attacker who has gained some level of access but does not possess full knowledge of the system. This type of testing allows for a more focused assessment of specific areas while still challenging the testers to identify vulnerabilities that may not be apparent with complete knowledge. By simulating an attacker with partial access, organisations can better understand how internal weaknesses might be exploited.
  • Full-Knowledge Testing (White Box):
    White box testing provides testers with comprehensive information about the in-scope systems, this could include architecture details, source code, network diagrams, and configuration files. This in-depth approach aims to uncover vulnerabilities that may not be easily identified through other testing methods. With access to the internal workings of the application or system, testers can perform a thorough analysis, looking for security flaws in the code, misconfigurations, and weaknesses in security controls in a shorter period of time. This type of testing is particularly valuable for identifying systemic vulnerabilities that could lead to serious breaches if not identified or addressed. It allows organisations to gain a deeper understanding of their security posture and make informed decisions about remediation efforts. The most common testing type as it provides the maximum amount of value for money.

Contact us today to schedule your penetration test or learn more about how we can help protect your organisation.

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