Some Definitions
Penetration testing (or pen testing) is a security exercise where a cybersecurity expert conducts simulated and ethical hacking attempts to find and exploit vulnerabilities in a computer system to enhance an organisation’s information security measures and security posture, acting according to organisational guidelines and within the defined and authorised scope. The goal is to identify security gaps and correct them in order of risk before unethical hackers can exploit them. Pen tests may focus on one or more areas of networks, systems, and applications.
Ethical hacking is an authorised attempt to hack a defined scope to uncover and rectify information security vulnerabilities.
Vulnerabilities are weak spots in a computer system’s defences that malicious attackers could take advantage of or exploit. Once cybercriminals gain unauthorised access to a system, they can run malicious code, install malware, and steal confidential and sensitive data.
Bug bounty programs offer a monetary reward to ethical hackers who identify a vulnerability or bug in an application across its development life cycle and report it to the app developer. Such programs leverage the hacker community's skills while reinforcing a company's penetration testing strategy and enhancing its security posture.
Malware refers to malicious software which is intrusive and developed by hackers and cybercriminals to access confidential data or damage and destroy computers and systems.
An organisation’s security posture refers to the totality of its cybersecurity readiness, which includes visibility into the security situation of its software, hardware, networks, services, and information.
Barriers to entry are physical barriers to an organisation’s premises and physical assets that prevent unauthorised access. They include locked doors that can be opened only with keys or authorised badges or by company receptionists and security guards.
How organisations respond to cyberattacks and data breaches constitutes incident response (IR). Responses include shutting down systems to thwart the attack,
examining logs to discover the timing of the attack and affected systems, informing affected stakeholders, and other investigations and decisions required to resume safe operations online.
The Internet of Things (IoT) refers to the enormous number of devices, running into billions, connected to the internet globally. IoT includes smart devices, such as household appliances or white goods, electronic toys, lighting, and security cameras, that may not require security measures or do not clarify their usage to users.
Phishing attempts are social engineering attacks that try to manipulate individuals into specific actions through direct email correspondence, usually aiming to access user data, such as login credentials and credit card numbers. Examples of phishing include getting users to open emails or messages and clicking malicious links leading to malware installation and ransomware attacks that can freeze the system or provide access to confidential and sensitive data.
Ransomware is malware that tries to infect desktops, servers and other target systems or networks by blocking access to them and their data. It typically uses data encryption or sets passwords that block access. Unblocking is possible only when the affected user pays the fee stated in the displayed message.
A red team test, conducted by internal or external Pen Testers, uses diverse hacking and social engineering methods to attack an organisation’s systems to access its networks and confidential data.
An SQL injection (SQLi) is a type of attack in which cybercriminals inject an SQL query containing malicious data into an application through input parameters, enabling access to sensitive data in the database.
A Man-in-the-Middle (MITM) attack refers to a threat wherein attackers place themselves between users and applications, aiming to eavesdrop or impersonate either of the parties, making it look as if the exchange of information is authentic. It is common to financial application users, SaaS (Software-as-a-Service) businesses, e-commerce, and other websites that require logging in. MITM attacks can result in the theft of personal information, including login credentials, account details, and credit card numbers.
The Penetration Testing Process
A penetration test methodology typically follows a structured approach that includes the phases of reconnaissance, scanning, vulnerability assessment, exploitation, and reporting.
Reconnaissance includes collecting information about the target system, either passively from publicly available resources or actively by interacting with the system. Scanning tools are then used to identify open ports. Running vulnerability assessments helps identify weaknesses in an organisation’s computer systems, networks, and applications, factoring in the data from reconnaissance and scanning. The process helps detect typical loopholes, such as misconfigurations, weak passwords, or outdated software, and more complex and sophisticated vulnerabilities that skilled and malicious attackers could leverage.
Based on the vulnerabilities that have been identified, Pen Testers research and develop new pen testing methodologies and simulated attacks, factoring in critical organisational variables, such as costs, complexities, risks, and resources involved.
They may customise authorised exploits on identified vulnerabilities by scripting and coding them or modifying existing pen testing tools. It is also vital to design and execute simulated social engineering attacks to assess the human element of security and to assess the physical security of systems, servers, and other network devices on the organisation’s premises.
Once all the necessary documentation is in place to ensure legal and ethical compliance, Pen Testers may launch remote or on-site simulated attacks while ensuring minimal impact on business operations. They document, analyse, and present the procedures and findings through detailed reports to IT and leadership teams and non-technical stakeholders. Along with describing the vulnerabilities and prioritising them based on their criticality, Pen Testers also recommend mitigation strategies, which they help implement and evaluate to enhance an organisation’s overall security posture.
Black-Box, White-Box & Grey-Box Testing
Black-box testing places Pen Testers in the position of the average hacker without sharing knowledge of the target system's internal features. Pen Testers using this technique do not have any architecture diagrams or source code that is not publicly available. Black-box testing aims to discover system vulnerabilities that may be exploited from outside the target network, using dynamic analysis of active programs and systems within it. However, if the testers do not succeed in breaching the perimeter, they cannot discover or fix internal vulnerabilities.
Grey-box testing allows testers the access and knowledge that users have and some awareness of a network’s internal features, such as its design and architecture documentation, and an internal account. This technique affords a more targeted and effective assessment of a network's security, particularly within its perimeter, than black-box testing. It simulates the position of a malicious attacker with longer-term network access than the average hacker.
White-box testing is also known as clear-box, open-box, auxiliary, or logic-driven testing. Diametrically opposite to black-box testing, it allows Pen Testers complete access to system features, such as source code and architecture documentation. However, given the available data to enable vulnerability assessment, white-box testing can be lengthy. It involves using static and dynamic analytical tools and techniques to evaluate a system’s internal and external vulnerabilities thoroughly.
Types of Penetration Testers
Network Penetration Testers specialise in testing servers, routers, switches, firewalls, and other network devices and scanning ports of entry. They aim to identify and exploit network infrastructure vulnerabilities, bypassing network security controls and gaining unauthorised access to understand how to strengthen network security measures. Some attacks they protect businesses from include firewall misconfiguration and bypass, database attacks, man-in-the-middle (MITM) attacks, and router attacks.
Web Application Penetration Testers focus on assessing, exploiting, and improving the security of websites, web portals, web-based services, and other web applications. Their tasks include architecture analysis, tests for typical vulnerabilities, such as SQL injection, and validating the adequacy of web-based security controls. They identify vulnerabilities in databases, source code and backend networks, prioritise them, and suggest risk-mitigation techniques.
Mobile Application Penetration Testers work with mobile applications (except mobile APIs and servers), evaluating their operating environment and architecture, analysing their security and code, testing for mobile-app-related vulnerabilities, and checking the security of an app’s storage, communication, and authentication mechanisms. Static analysis methods perform reverse engineering on extracted source code and metadata to discover security gaps. Dynamic analysis detects the application’s vulnerabilities while it runs on a device or server.
Wireless Penetration Testers deal with wireless networks, including Wi-Fi networks. They identify and exploit vulnerabilities in the security configurations of wireless access points and encryption. They aim to try and enter the network through a security breach or intercept wireless communications to recommend measures to mitigate the risk of the misconfiguration of wireless routers, session reuse, and unauthorised wireless devices.
Social Engineering Penetration Testers specialise in exploiting human vulnerabilities through social engineering techniques, given that humans are viewed as the most vulnerable links in the security chain. These testers conduct phishing attacks, impersonate individuals to gain sensitive information, and assess the vulnerability of individuals, groups, or processes in an organisation to manipulation and deception.
Physical Penetration Testers attempt to gain entry into the restricted areas of an organisation’s physical premises by evading access controls, surveillance systems, security procedures, and security staff. Their purpose is to evaluate the effectiveness of physical security controls, such as locks, doors, cameras, or sensors, in safeguarding a business’s physical assets and preventing access to sensitive zones, such as server rooms. They also try to prevent social engineering threats, tailgating, and badge cloning.
Red Team Penetration Testers work as ethical hackers and try to cause security breaches based on the findings of vulnerability assessments. Red team testing is based on military training exercises and uses an offensive or adversarial approach. The blue team responds with defensive security. Regular pen testing is typically limited by the task scope. However, red team pen testing entails simulated attacks using technical and non-technical methods in the physical, digital, and social contexts to help evaluate an organisation’s overall security posture.
IoT (Internet of Things) Penetration Testers probe and tackle vulnerabilities in smart home devices, industrial IoT systems, and other connected devices and data ecosystems. IOT pen testing can be complicated due to the use of diverse technologies and the numerous points of attack possible. IoT pen tests identify flaws in various layers to enhance the security of an object’s overall environment. You may audit the hardware software, APIs, and web and mobile interfaces or focus on a specific area with identified security issues.
Other types of Pen Testers include Cloud Penetration Testers (for cloud-based infrastructure and environments), Blockchain Penetration Testers (for decentralised applications (DApps), smart contracts and blockchain networks), Embedded System Penetration Testers (for medical devices and automotive and industrial control systems), and Thick Client Application Penetration Testers (for desktop or standalone applications).
Penetration Testers vs Ethical Hackers
With their titles often used interchangeably, the roles and objectives of Penetration Testers and ethical hackers have several overlaps as both are vital contributors to
strengthening an organisation’s cybersecurity defences. However, ethical hacking is a broader field, with penetration testing as one of its areas.
Like Pen Testers, ethical hackers, also termed white hat hackers, are cybersecurity experts who conduct authorised assessments to identify security flaws and vulnerabilities in an organisation’s security posture, including its computer systems, networks, and applications. However, while Pen Testers tend to follow a relatively structured methodology, ethical hackers may stretch their repertoire to include innovative and even unconventional approaches to reveal vulnerabilities that may have been missed in earlier assessments.
Professionals in the field may go by either title, depending on their organisation, certifications, skill set, interests, and projects.
Penetration Tests vs Vulnerability Scans/Assessments
Isolated and automated vulnerability scans or assessments generate a list of vulnerabilities, but they are passive because they only report security gaps, leaving it to the stakeholders and their IT teams to fix them on priority or confirm whether they are false positives and need a scan rerun.
Pen tests cannot be automated but need Pen Testers to use the identified vulnerabilities from vulnerability scans to plan and implement appropriate, authorised, and simulated cyberattacks on an organisation’s systems, networks, and applications. Using detailed pen testing procedures to detect security lapses, thorough analysis and systematic reporting, Pen Testers can prioritise and recommend effective risk management strategies and remediations to organisations.
Some Pen Testing Tools
The wide range of tools that make the work of Pen Testers faster and more efficient include Kali Linux (a popular operating system for pen testing), Nmap (a port scanner for network discovery), Wireshark (a packet sniffer to analyse traffic on your network), John the Ripper (an open-source password cracker), Burp Suite (to test application security), Nessus (a vulnerability assessment tool), and OWASP ZAP Proxy (a web application security scanner).
White, Black & Grey Hat Hackers
White hat hackers are ethical hackers authorised to exploit computer systems to probe, uncover, and fix an organisation’s security vulnerabilities. Although they access sensitive information, they do not aim to exploit it or disrupt the system and company operations for personal gain. Their overarching aim is to protect their clients' or employers’ systems and networks by securing the loopholes they discover before unethical hackers find and exploit them.
Black hat hackers are unethical hackers not hired by organisations to look for vulnerabilities but still do so to exploit them for financial gain, for instance, by accessing the credit card information of a business’s customers. Some work for rogue nations to cause infrastructure and other disruptions in enemy nations.
Grey hat hackers fall between the two categories of white and black hat hackers. While their work can be useful, it may still be viewed as ethically doubtful.
Why Some Employers Use the Services of Pen Testers
Software development firms, cybersecurity consultancies, network infrastructure specialists, and other technology companies typically have their in-house teams of Pen Testers to ensure that their systems and products are secure.
Cybersecurity consultancies provide penetration testing to clients across diverse industries as part of their specialised services. Their Pen Testers work with clients to conduct vulnerability assessments, conduct authorised and simulated cyberattacks, and recommend security posture enhancements based on their findings.
Pen Testers employed by government agencies engaged in critical areas, such as defence, intelligence, and legislation, help assess and enhance the security of their information systems and infrastructure.
Financial institutions, such as banks and insurance companies, employ Pen Testers to secure the robustness of their cybersecurity measures and also ensure regulatory compliance.
E-commerce, online payment processing, and digital services must strictly secure customer data to uphold trust and protect the business from financial damage. Pen Testers help mitigate the risk of data breaches by assessing and identifying threats and preventing them.
Since protecting sensitive patient data from cyberattacks and data breaches is critical, healthcare providers and medical research institutions employ Pen Testers to probe, detect and resolve vulnerabilities in their networks, applications, and medical devices.
Energy and utility companies employ Pen Testers to assess and enhance the security of their critical infrastructure to stall off current and potential threats.
Current Scenario
The employment outlook of a particular profession may be impacted by diverse factors, such as the time of year (for seasonal jobs), location, employment turnover (when people leave current jobs), occupational growth (when new roles are created), size of the occupation and industry-specific trends and events that affect overall employment.
As networks, applications, information management needs, and systems grow more complex and critical, their vulnerabilities also increase. Pen Testers will continue to be needed to leverage technology in preventing potential cyberattacks and preparing for and minimising their impact if they do occur.
Despite growing educational pathways to specialise in cybersecurity, professionals remain in short supply. However, cybersecurity specialists in related areas, such as applications, IoT, SCADA (Supervisory Control and Data Acquisition), or blockchain pen testing, will remain in high demand with companies to test their products and ensure legal compliance.
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Conclusion
Forewarned is forearmed. Pen Testers contribute to an organisation’s cybersecurity strategy by conducting planned and ethical simulations of cyberattacks. They pinpoint and fix vulnerabilities in the IT infrastructure before malicious attackers exploit them. It is vital that Pen Testers update their skills to counteract evolving cyberattack threats and minimise the risk of data breaches and consequent financial harm to businesses.
Advice from the Wise If you already work in an IT role in a company, a creative and economical way to build and practise your pen test toolkit is to convert an older or unused PC or laptop into a test system. You may also use virtualised software to access and test multiple systems from a single test system.