Fighting Phishing Security 2021

What is penetration testing and how pentesting works?

date: 5 January 2023
reading time: 5 min

For cybercriminals, cyberattacks mean huge business. For their victims, they mean incredible losses – in terms of money, data and reputation. One of the best ways to avoid them is via regular penetration testing. Let’s look at what it is and how to use it to your advantage.

Keen to know more about penetration testing and how it can help you stay better protected? Here’s our comprehensive guide with answers to most important questions on the subject!

Penetration Test: the first line of cyber defense

Penetration test, also known as pen tests, is a simulated, authorised and controlled cyberattack, needed to evaluate the security of an IT infrastructure and various apps. Performed by cybersecurity specialists who use the same tools as hackers, it is an indispensable way to get to know vulnerabilities in the system or in an app and address them before they get exploited by actual criminals.

To give you an example, pen testing is like asking someone to dress as a burglar, cover their face and try to get into your home when you are out, so that you can learn whether your locks are really as effective as you imagine them to be or if your alarm works the way it should. If not, you can change them or add some additional protection, and greatly improve your security.

A look back: the evolution of Penetration Tests

Penetration testing has evolved significantly over the years as organisations strive to strengthen their cybersecurity defences.

In the early days of penetration testing (pre-2000), the focus was primarily on testing network security. Penetration testers would manually identify vulnerabilities and attempt to exploit them to gain unauthorised access. This involved techniques like network scanning, port scanning, and vulnerability scanning.

In the early 2000s, standardised methodologies for penetration testing started to emerge. Frameworks like Open Source Security Testing Methodology Manual (OSSTMM) and Penetration Testing Execution Standard (PTES) provided structured approaches to conducting penetration tests. These methodologies emphasised the importance of comprehensive testing, including network, application, and physical security.

In the mid-2000s, with the rise of web applications and their increasing vulnerabilities, penetration testing began to focus more on application security. Testers shifted their attention to identifying vulnerabilities in web applications, such as SQL injection, cross-site scripting (XSS), and insecure session management. This led to the development of specialised tools and techniques for web application penetration testing.

Late 2000s was marked by automation and tool development. As the complexity of systems increased, penetration testers started leveraging automated tools to streamline the testing process. Tools like Metasploit, Nessus, and Burp Suite became widely used, enabling testers to automate vulnerability scanning, exploit execution, and reporting. While automation improved efficiency, manual testing and analysis remained essential for uncovering sophisticated vulnerabilities.

In recent years, the focus has shifted towards continuous testing and integration of security practices into the DevOps pipeline (DevSecOps). Penetration testing is no longer a one-time event but an ongoing process integrated into the security development lifecycle. Automated security testing tools, code reviews, and security testing as part of continuous integration/continuous delivery (CI/CD) pipelines help identify vulnerabilities early and enable faster remediation. 

With the growth of cloud computing and Internet of Things, penetration testing expanded to cover the unique challenges associated with these environments. Testers assess the security of cloud infrastructure, containers, serverless architectures, and IoT devices, identifying vulnerabilities and misconfigurations that could expose organizations to risk. 

Throughout its evolution, penetration testing in security has become more comprehensive, proactive, and sophisticated. It has moved beyond a reactive approach to a proactive and continuous security assessment practice, helping organisations identify weaknesses, improve defenses, and stay ahead of evolving cyber threats. 

Diving into the details: the mechanics of pentesting

As a systematic process of assessing the security of computer systems, networks, or applications to identify vulnerabilities and potential security risks, pentesting involves several key steps, which can vary depending on the scope and objectives of the engagement.

The hacker’s mindset: simulating cyber attacks

The mechanics of pentesting require a combination of technical skills, deep knowledge of security vulnerabilities and exploitation techniques, and the ability to think like a hacker to identify vulnerabilities, test defenses, and evaluate an organisation’s security posture. This process aims to uncover potential weaknesses before malicious actors can exploit them, so having hacker’s mindset is one of the key elements of the job.

How does penetration testing work: stages of penetration testing

Here is an overview of the typical mechanics involved in a penetration test:

  1. Planning and scoping

    This initial phase involves defining the scope and objectives of the pentest. The pentester works closely with the client to understand their specific requirements, identify target systems or applications, and determine the rules of engagement, including any limitations or restrictions.

  2. Reconnaissance

    In this phase, the pentester gathers information about the target systems or applications. This can involve passive reconnaissance, which includes collecting publicly available information, or active reconnaissance, which includes activities like network scanning, port scanning, or fingerprinting to identify potential entry points.

  3. Vulnerability scanning and enumeration

    The pentester uses automated tools or manual techniques to identify vulnerabilities in the target systems or applications. This typically involves vulnerability scanning tools, network mapping, service enumeration, and identifying weak configurations or software flaws.

  4. Exploitation

    In this phase, the pentester attempts to exploit the computer system weknesses to gain unauthorised access or escalate privileges. They may use various techniques, such as exploiting known vulnerabilities, conducting privilege escalation, or executing remote code.

  5. Post-exploitation and lateral movement

    Once initial access is gained, the pentester explores the target environment to move laterally and gain further access. They may attempt to pivot across different systems, escalate privileges, and maintain persistence within the target network or application.

  6. Data exfiltration or impact assessment

    Depending on the objectives of the pentest, the pentester may attempt to extract sensitive data to demonstrate the impact of a successful attack or assess the potential consequences of a breach. This step helps highlight the potential risks and their business impact.

  7. Reporting and documenting

    After the testing phase, the pentester prepares a comprehensive report that includes detailed findings, identified vulnerabilities, and recommended remediation measures. The report typically includes an executive summary, technical details, risk ratings, and actionable recommendations to improve the security posture.

  8. Remediation and retestingFollowing the penetration test, the client addresses the identified vulnerabilities based on the recommendations provided in the report. The pentester may perform a retest to verify that the reported vulnerabilities have been successfully remediated.

Strategies for penetration tests

When it comes to strategies used by penetration testers, the most common ones include:

Internal penetration test

Statistics show that the most dangerous cybercriminals are employees. Internal tests mimic an insider attack conducted by a user with access privileges and allow to assess the scale of damage an employee who decides to attack your system may do.

External penetration test

External testing allows to estimate how far an external attacker can get by attacking servers and devices exposed in public network by an organisation.

Blind penetration test

Blind tests mean tests conducted by people who have no prior knowledge of the company and its security systems. Very often the only information they get is the name of the organisation they are testing, which allow them to behave the way cybercriminals do.

Double blind penetration test

Double blind tests are blind tests taken to the next level. They mean that the pen testers do not have any information on the company they are assessing and that only a limited number of people within the organisation (often just one or two) know about the test.

Types of penetration testing and examples

Penetration testing encompasses various types that focus on different aspects of an organisation’s security. Here are some common types of penetration testing along with examples:

External network penetration testing

External network penetration testing means assessing the security of the organisation’s externally facing network infrastructure to identify vulnerabilities that could be exploited by simulated attack. Good examples are conducting port scanning, vulnerability scanning, and attempting to exploit weak configurations or outdated software.

Internal network penetration testing

Internal network penetration testing means evaluating the security of internal networks to identify potential risks arising from compromised internal systems or unauthorised access. Examples here are attempting to escalate privileges, move laterally across network segments, and gain access to sensitive resources

Social engineering testing

Social engineering testing can be split in two:

  • Phishing, meaning simulating phishing attacks to assess the organisation’s vulnerability to email-based social engineering. Examples are sending deceptive emails to employees, attempting to trick them into revealing sensitive information or performing actions that compromise security.

  • Pretexting, meaning using false pretenses or impersonation to manipulate individuals into divulging confidential information. Examples are posing as a trusted authority or service provider to gain access to sensitive data or systems.

Physical penetration testing

Physical Penetration Testing can be split in two:

  • Physical access testing, meaning evaluating the physical security controls of an organisation’s premises, including buildings, data centres, or secure areas. Examples here are attempting unauthorised entry, bypassing physical access controls, or tampering with physical security devices.

  • Tailgating testing, which means assessing the organisation’s vulnerability to unauthorised individuals gaining access by following authorised personnel. Examples are attempting to enter secure areas by closely following an authorised employee without proper authentication.

Wireless penetration testing

Wireless penetration testing means:

  • Wi-Fi network testing – assessing the security of wireless networks, including Wi-Fi networks, to identify vulnerabilities that could be exploited by unauthorised users. Examples are attempting to bypass encryption, crack weak passwords, or perform man-in-the-middle attacks on wireless communications.

  • Bluetooth testing – evaluating the security of Bluetooth-enabled devices and networks, identifying potential vulnerabilities that could lead to unauthorised access or data leakage. Good examples are assessing the pairing process, analysing Bluetooth communications for security weaknesses, and attempting to exploit vulnerabilities in Bluetooth implementations.

Application penetration testing

Application penetration testing, also known as application security testing or app pen testing, is a type of security assessment that focuses specifically on identifying vulnerabilities in software applications. It involves testing the security of web applications, mobile applications, or other types of software to identify potential weaknesses that could be exploited by attackers.

The importance of penetration testing in today’s digital age

Penetration testing is of paramount importance for businesses in today’s digital age as it:

  1. Identifies vulnerabilities in computer systems, networks, and applications. It provides organisations with insights into potential security weaknesses that could be exploited by attackers. By proactively identifying vulnerabilities, companies can take appropriate measures to mitigate risks and enhance their overall security posture.

  2. Simulates real-world cyber attacks, providing a realistic assessment of an organisation’s security defences. It allows companies to understand how their systems and networks would withstand various attack scenarios, which enables them to identify gaps in their security controls, refine incident response processes, and strengthen their defences accordingly.

  3. Protects sensitive data by uncovering vulnerabilities that could lead to unauthorised access, data exfiltration, or manipulation of sensitive information. By identifying these weaknesses, organisations can implement measures to protect their data and maintain the trust of their customers and stakeholders.

  4. Helps organisations demonstrate compliance with legal requirements by conducting regular assessments of their security controls. It provides evidence of due diligence and proactive efforts to protect sensitive information, which is crucial in meeting regulatory obligations.

  5. Increases incident response preparedness which helps identify areas for improvement, optimise incident response plans, and enhance the organisation’s overall resilience against cyber threats.

  6. Gives third-party assurance by assessing the security of these external entities and validating their security controls. This helps ensure that third parties are adequately protecting sensitive data and mitigating security risks that could impact the organisation.

  7. Allows for proactive risk management. By identifying vulnerabilities and weaknesses before they are exploited by malicious actors, organisations can prioritise and allocate resources to address the most critical security risks. This proactive approach reduces the likelihood of successful cyber attacks and minimises potential financial and reputational damages.

  8. Increases security awareness. Penetration testing serves as an educational tool to raise security awareness among employees. It highlights the real-world consequences of security vulnerabilities and encourages a security-conscious culture within the organization. By experiencing simulated attacks, employees become more vigilant and better equipped to identify and report potential security incidents.

In today’s interconnected and rapidly evolving digital landscape, organisations must be proactive in identifying and mitigating security risks. Penetration testing provides a critical mechanism to assess the effectiveness of security controls, protect sensitive data, and strengthen an organisation’s overall cyber security defences.

Penetration testers: who should perform pen tests?

As important cybersecurity tests that are vital to the safety of the organisation, pen tests should be performed by a testing team, composed of experienced and skilled IT and cyber security professionals.

Pentesters start with getting to know the organisation they are about to assess and the systems used, they then conduct the tests and check the organisation’s security posture by using exactly the same tools as hackers. Finally, they come up with a list of vulnerabilities, problems and the ways to address them to achieve the best possible level of security.

How often should you conduct pen tests?

The cyberworld keeps evolving and cybercriminals are coming up with new ways of attacking every day. This is why it is of paramount importance to conduct pen tests on regular basis, making sure no new viruses or malicious strategies will compromise the safety of your organisation, its data and money.

The best approach is to do pen tests every time there is a substantial change of the app or the infrastructure. But pen tests are crucial even if there are no changes – in such cases it’s best to perform them at least annually to check if the updates process is working fine and whether there are no new vulnerabilities, born as a result of new techniques used by cybercriminals.

How much does penetration testing cost?

The cost of penetration testing can vary widely depending on several factors, including the scope of the engagement, the complexity of the systems being tested, the level of expertise required, and the reputation and location of the testing service provider. Some key factors that influence the cost of penetration testing include:

  1. Scope and objectives

    A larger and more complex infrastructure will require more time and resources to thoroughly assess, resulting in higher costs.

  2. Testing frequency

    Organisations that conduct regular testing as part of their security program may negotiate a contract for recurring engagements, which could provide cost savings compared to one-time engagements.

  3. Depth of testing

    Deeper testing that involves more manual efforts and sophisticated attack simulations may require higher expertise and resources, leading to increased costs.

  4. Skill and expertise level

    Highly skilled professionals with specialised knowledge and certifications often come at a premium cost compared to less experienced testers.

  5. Reporting and documentation

    A comprehensive report that includes detailed findings, risk assessments, and actionable recommendations may require more time and effort to produce, resulting in higher costs.

  6. Additional services

    Some penetration testing service providers may offer additional services, such as retesting after remediation, follow-up assessments, or specialized compliance testing. These additional services may incur additional costs.

It’s important to note that cost should not be the sole determining factor when selecting a penetration testing service. The quality and expertise of the testing team, the depth of testing provided, and the reputation of the service provider should also be considered.

To get an accurate cost estimate for penetration testing, it is recommended to reach out to reputable service providers, share the specific requirements and objectives of the engagement, and request a detailed proposal that outlines the scope, approach, deliverables, and associated costs. This will help you understand the specific cost implications based on their unique needs.

Ethical considerations in penetration testing

Ethical considerations play a crucial role in conducting penetration testing to ensure that the assessment is conducted responsibly and with respect for legal and ethical boundaries.

Simulated attack should only be conducted with the explicit consent and authorisation of the organisation or system owner. Engagements should be formally documented through legal agreements or contracts that outline the scope, objectives, and rules of engagement. The process must adhere to applicable laws, regulations, and industry standards. Testers should ensure they are not violating any laws or regulations during the assessment, including unauthorised access, data privacy, or intellectual property rights.

Clear boundaries and limitations should be defined and communicated to both the testing team and the organisation, and penetration tester should handle and protect any sensitive data encountered during the assessment with utmost care. What’s more, pentesters should minimise the impact on the target systems or networks. The testing activities should be designed to avoid disruption of normal business operations, unintentional damage, or interference with critical systems.

Pen testers have a responsibility to provide clear and comprehensive reporting of their findings, including vulnerabilities, risks, and recommended remediation measures. They should adhere to high professional standards, act with integrity throughout the engagement and continuously update their knowledge and skills to keep pace with evolving threats and technologies.

Potential challenges and risks in penetration testing

Penetration testing, like any security assessment, carries certain challenges and risks that need to be considered. Understanding these challenges helps organisations and penetration testing teams mitigate potential risks and ensure a successful engagement. Some common challenges and risks associated with penetration testing include:

  1. Impact on production systems

    The testing activities, if not properly controlled, may inadvertently cause disruptions or impact the availability of production systems. The testing team should take precautions to minimise any potential negative effects on critical business operations.

  2. False positives and negatives

    Pen test may produce false positives (indicating vulnerabilities that do not exist) or false negatives (missing actual vulnerabilities). The testing team should carefully analyse and validate findings to avoid reporting inaccurate results, which can waste time and resources.

  3. Confidentiality and data protection

    During the testing process, the penetration testers may come across sensitive information or confidential data. It is crucial to handle such information with utmost care and ensure its protection and confidentiality throughout the engagement.

  4. Unauthorised access

    If not properly managed, pen testing activities can unintentionally lead to unauthorised access or unintended consequences. Testers should follow strict rules of engagement and have explicit authorisation to avoid legal or ethical violations.

  5. Impact on third parties

    Testing activities may inadvertently affect third-party systems or networks connected to the target environment. Care should be taken to minimise any impact on systems outside the defined scope and ensure proper consent and coordination with relevant stakeholders.

  6. Regulatory compliance

    Penetration testing services should align with applicable legal and regulatory requirements. Organisations must ensure that their engagement with penetration testing teams complies with relevant laws, data protection regulations, and industry-specific compliance requirements.

  7. Lack of coordination

    In larger organisations, coordination and communication between the penetration testing team and internal stakeholders may present challenges. Effective coordination and clear lines of communication are essential to ensure the testing aligns with business objectives and security needs.

  8. Human error and bias

    Penetration testing services are conducted by humans who are susceptible to errors, biases, or subjective judgments. Penetration testing company should be diligent in their assessments, follow established methodologies, and have regular quality assurance processes in place to minimise the impact of human factors.

Addressing these challenges and risks requires careful planning, clear communication, and collaboration between the organisation and the penetration testing team. It is essential to establish proper rules of engagement, define objectives and limitations, and maintain open lines of communication throughout the engagement to ensure a successful and effective penetration testing exercise.

Future trends and evolution of penetration testing

The field of authorized simulated attacks is constantly evolving to keep pace with emerging technologies, evolving threat landscapes, and changing security requirements. Here are some future trends and potential areas of evolution in the field of penetration testing:

  • Cloud-based penetration testing: as organisations increasingly adopt cloud computing, there is a growing need for penetration testing specific to cloud environments. Penetration testers will need to develop expertise in assessing the security of cloud platforms, infrastructure-as-a-service (IaaS), platform-as-a-service (PaaS), and software-as-a-service (SaaS) offerings.

  • Internet of Things (IoT) penetration testing: with the proliferation of IoT devices, there will be an increasing demand for penetration testing focused on securing these interconnected devices. Penetration testers will need to understand the unique challenges of assessing IoT device security, including firmware vulnerabilities, communication protocols, and the potential impact of compromised IoT devices on overall network security.

  • Artificial Intelligence and Machine Learning in penetration testing: the integration of artificial intelligence (AI) and machine learning (ML) technologies into penetration testing tools and methodologies will enhance automation, improve vulnerability detection, and assist in identifying patterns and anomalies in network behaviour. AI/ML-powered tools can help testers analyse vast amounts of data and adapt to evolving attack techniques.

  • DevSecOps and continuous penetration testing: the shift towards DevSecOps practices emphasises integrating security into the development and deployment process. Penetration testing will increasingly become part of the continuous integration and continuous delivery (CI/CD) pipeline, enabling organisations to identify and remediate vulnerabilities early in the development lifecycle.

  • Red team operations and adversary simulations: red team operations, which simulate real-world attacks, will become more sophisticated and comprehensive. Organisations will focus on adversary simulations to assess their detection and response capabilities against advanced persistent threats (APTs) and sophisticated attack scenarios.

  • Deepfake and voice biometrics testing: the rise of deepfake technology and the use of voice biometrics pose new challenges for security. Penetration testers will need to explore techniques to assess the security of voice authentication systems, detect deepfake audio, and identify vulnerabilities in voice recognition technologies.

  • Physical security testing: penetration testing will extend beyond digital systems to include physical security assessments. Organisations will conduct tests to evaluate physical access controls, surveillance systems, and social engineering vulnerabilities at physical locations.

  • Compliance-driven penetration testing: with the increasing emphasis on regulatory compliance, penetration testing will need to align with specific industry standards and compliance frameworks. Testers will incorporate specific compliance requirements into their assessments and provide organizations with assurance of compliance.

  • Bug bounty programs: organisations will continue to leverage crowdsourced security through bug bounty programs. These programs incentivise ethical hackers to identify misconfigurations and provide organisations with an ongoing source of external security testing.

  • Ethical considerations and responsible testing: the ethical hacking (and legal considerations in penetration testing( will become even more critical. Testers will need to adhere to strict code of ethics, respect privacy, and ensure that testing activities do not cause harm to systems or violate legal boundaries.

Overall, penetration testing will evolve to meet the changing landscape of technology and security flaws. It will become more specialised, integrated into development processes, and encompass a wider range of testing scenarios to ensure comprehensive security assessments. Continuous learning, keeping up with emerging technologies, and staying abreast of evolving attack techniques will be essential for penetration testers to provide effective and valuable security assessments in the future.

The advent of automated pen testing

Automation is the new gold. Automated penetration testing tools can significantly enhance efficiency, scalability, and coverage in security assessments. They can help organisations identify common security holes and streamline certain aspects of testing. However, they are most effective when integrated into a comprehensive testing program that combines automated scanning with manual expertise, analysis, and validation. A balanced approach leveraging both manual and automated testing ensures a thorough and accurate assessment of an organisation’s security posture.

Closing thoughts: the enduring necessity of penetration tests

In today’s rapidly evolving digital landscape, the enduring necessity of penetration testing cannot be overstated. As organisations increasingly rely on technology to conduct their business operations, the potential risks and consequences of cyber attacks continue to grow. Penetration testing provides a vital mechanism for organisations to proactively assess their IT system’s security and mitigate risks before malicious actors exploit them.

It is vital though to recognise that penetration testing is not a one-time event but an ongoing process. The evolving nature of technology and the ever-changing threat landscape necessitate regular assessments to keep up with emerging risks. Organisations should consider incorporating penetration testing into their overall security strategy, ensuring that it becomes a recurring practice alongside other security measures such as security vulnerability management, security awareness training, and incident response planning.

Additionally, engaging experienced and reputable penetration testing professionals is crucial. Their expertise, knowledge of the latest attack techniques, and adherence to ethical guidelines ensure that testing is conducted responsibly, without causing harm or disruption to systems or violating legal boundaries.

If you are keen to get advice from specialists in all kinds of penetration testing services, do get in touch. Our experienced team of experts will be happy to help!

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