Wat is een pentest?

Meaning

A penetration test (pentest,) is a simulated attack on a computer system to evaluate its security. Pentesters use the tools, techniques and processes that a malicious attacker would deploy to find and demonstrate the effects of weaknesses in a system. A pentest simulates various tactics and techniques that could threaten an organization. This examines a system's ability to withstand sophisticated attacks from authenticated and unauthenticated positions. With an appropriate scope, a pen test can basically assess the security of any aspect of a system.

Content

What is the purpose of a pen test?

Applications and systems should be designed in a way that minimizes the risk of security breaches. A pen test provides insight into how well that goal has been achieved. On this basis, conducting (or having conducted) a pen test can help organizations with:

Finding weaknesses in systems

Assess the effectiveness of security measures

Supporting regulatory compliance around data protection and security (e.g. ISO 27001, DigiD, BIO)

Understanding of the organization's current security position that can be used to set budget priorities

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Who conducts pen tests?

It is best to have a pen test performed by someone with little to no prior knowledge of how the system is secured because they can uncover blind spots that have been overlooked by the developers who built the system. For this reason, outside contractors are usually hired to conduct the tests. These contractors are often called "ethical hackers" because they are hired to break into a system with permission and for the purpose of improving security.

Many ethical hackers are experienced developers with advanced degrees and certification in pen testing. On the other hand, some of the best ethical hackers are self-taught. Some are even reformed criminal hackers who now use their expertise to fix security vulnerabilities rather than exploit them. The best candidate to perform a pen test can vary greatly depending on the target company and the type of pen test they want to perform.

For what reasons do organizations conduct pen tests?

A pen test provides insight into the most vulnerable aspects of a system. It also serves as a preventive security analysis, allowing organizations to fix discovered vulnerabilities before potential attackers can exploit them.

Here are four reasons why organizations should conduct pen tests:

Risk assessment. The number of distributed DoS, phishing and ransomware attacks is increasing dramatically, putting most businesses at risk. Considering how dependent businesses are on technology, the consequences of a successful Cyber attack have never been greater. For example, a ransomware attack can leave an organization without access to the data, devices, networks and servers it relies on to do business. Thus, a successful attack can result in millions of dollars in lost revenue. A pen test uses the point of view of hackers to discover and mitigate cybersecurity risks before they are exploited. This helps IT leaders make informed security upgrades that minimize the chances of successful attacks.

Safety Awareness. Technology is constantly evolving, as are the methods used by cybercriminals. If companies want to successfully protect themselves and their assets from these attacks, they must be able to update their security measures at the same rate. The downside, however, is that it is often difficult to know what methods cybercriminals are using and how they can be used in an attack. By conducting a pen test, organizations can quickly and effectively identify, update and possibly replace vulnerable parts of their systems.

Reputation. A data breach can put an organization's reputation at risk, especially if it becomes public. Customers may lose confidence in the organization and stop buying products, while investors may hesitate to invest in an organization that does not take its digital security seriously. A pen test helps protect an organization's reputation by identifying proactive risk mitigation measures.

Compliance. Industries, including healthcare, banking and service providers, are taking compliance and regulation seriously and incorporating pentesting as part of their compliance efforts. Pentesting is an effective way to meet the requirements of various common legislations and standards frameworks such as the General Data Protection Regulation (AVG) and ISO 27001. Thus, by conducting regularly scheduled pen tests, organizations can stay on top of their compliance needs.

What stages does a pen test consist of?

A pen test simulates attacks by motivated adversaries. To do this, testers usually follow a plan that includes the following steps:

Exploration. As much information about the target as possible is gathered from public and private sources to determine the attack strategy. Sources include Internet searches, retrieving domain registration information, social engineering, non-intrusive scanning of networks and sometimes even dumpster diving. This information helps pentesters map the target's attack surface and potential vulnerabilities. What the reconnaissance process includes can vary with the scope and objectives of the pen test; it can be as simple as making a phone call to go over the functionality of a system.

Scanning. Pentesters use tools to probe the Web site or system for vulnerabilities, including open services, application security problems and open source vulnerabilities. Pentesters use a variety of tools based on what they find during reconnaissance and during testing.

Gain access. Motives of attackers may include stealing, altering or deleting data, moving funds or simply damaging a company's reputation. For each test case, pentesters determine the best tools and techniques to gain access to the system, whether through a vulnerability such as SQL injection or through malware, social engineering or something else.

Maintain access. Once pentesters gain access to the target, their simulated attack must persist long enough to achieve their goal: exfiltrate data, modify it or abuse functionality. The key is to demonstrate the potential impact.

Analysis. The findings of the pen test are analyzed, based on which an action-oriented report is prepared. The report should clearly document and contextualize vulnerabilities so that the organization can address the security risks found.

How much access do pentesters get?

Depending on the objectives of a pen test, testers are given varying degrees of information about or access to the target system. In some cases, the pentest team chooses one approach at first and stays with it. In other cases, the test team develops its strategy as knowledge of the system increases during the pen test. There are three levels of access for a pen test:

a total lack of information: In a black box pentest, the tester receives no information at all. In this case, the pentester follows the approach of an unauthorized attacker, from initial access and execution to exploitation. This scenario can be seen as the most authentic, showing how an adversary would attack and compromise an organization without prior knowledge.

Grey box: In a grey box pen test, only limited information is shared with the tester. Usually this is in the form of login credentials. Grey box tests are useful for understanding the degree of access a privileged user could have and the potential damage they could cause. Grey box tests balance depth and efficiency and can be used to simulate an insider threat or an attack through the network perimeter.

White box: In a white box pen test, complete network and system information is shared with the tester, including network maps and credentials. This helps save time and reduce the overall cost of a job. A white box pen test is useful for simulating a targeted attack on a specific system using as many attack vectors as possible.

What pentest types are there?

A thorough approach to Cybersecurity is essential for optimal risk management. This includes having all systems and applications that are potential targets for attackers tested.

Web Applications. Testers examine the effectiveness of security controls and look for hidden vulnerabilities, attack patterns and other potential security flaws that could lead to a Web application being compromised.

Mobile applications. Using both automated and extensive manual testing, testers look for vulnerabilities in application binaries running on the mobile device and associated server-side functionality. Server-side vulnerabilities include session management, cryptographic problems, authentication and authorization issues and other common vulnerabilities in Web services.

(Wi-Fi) Networking. A Wi-Fi network pen test identifies common to critical vulnerabilities in a remote network and systems. Experts use a checklist of test cases for encrypted transport protocols, SSL certificate scoping issues, use of administrative services and more.

Cloud. A cloud environment differs significantly from traditional on-premises environments. Typically, security responsibilities are shared between the organization using the environment and the cloud service provider. Therefore, cloud pen testing requires specialized skills and experience to scrutinize different aspects of the cloud, such as configurations, APIs, different databases, encryption, storage and security controls.

Containers. Containers coming from Docker often contain vulnerabilities that can be exploited at scale. Misconfiguration is also a common risk associated with containers and their environments. Both risks can be exposed with expert pen testing.

Embedded devices (IoT). Embedded / Internet of Things (IoT) devices such as medical devices, cars, home appliances, oil rig equipment and watches have unique requirements for software testing due to their longer life cycles, remote locations, power constraints, regulatory requirements and more. Experts perform a thorough communications analysis along with a client/server analysis to identify defects most important to the relevant use case.

Mobile devices. Pentesters use both automated and manual analysis to find vulnerabilities in application binaries running on the mobile device and associated server-side functionality. Vulnerabilities in application binaries can include authentication and authorization issues, client-side trust issues, misconfigured security controls and cross-platform development framework issues. Server-side vulnerabilities can include session management, cryptographic issues, authentication and authorization issues and other common vulnerabilities in Web services.

APIs. For the OWASP API Security Top 10 list, both automated and manual techniques are used when performing a pen test. Some of the security risks and vulnerabilities that testers look for are broken object-level authorization, user authentication, overexposure of data, lack of resources/speed limitation, and more.

CI/CD pipeline. Modern DevSecOps practices integrate automated and intelligent code scanning tools into the CI/CD pipeline. In addition to static tools that find known vulnerabilities, automated pentest tools can be integrated into the CI/CD pipeline to mimic what a hacker might do to compromise an application's security. Automated CI/CD pentests can discover hidden vulnerabilities and attack patterns that static scanning fails to detect.

How often should pen tests be performed?

How often pen tests should be performed depends on many factors, but most security experts recommend doing it at least once a year because it can detect emerging vulnerabilities, such as zero-day threats. According to Google at least 41 zero-day threats had surfaced by 2022.

Organizations should consider the following factors when planning pen tests:

Size of the organization. Larger organizations can incur greater monetary and reputational losses if they fall prey to cyber attacks. Therefore, they should invest in regular security testing to prevent these attacks.

Budget. Pentests should be based on a company's budget and how flexible it is. For example, a larger organization might be able to conduct annual pentests, while a smaller organization might only be able to afford it once every two years.

Regulation. Depending on the type of organization and relevant regulations, certain organizations within banking and health care, for example, are required to conduct mandatory pen tests.

In addition to regularly scheduled pen tests, organizations should also conduct security tests when the following events occur:

New network infrastructure or devices are added to the network.

Upgrades are performed on existing applications and equipment.

Patches for security are installed.

New office locations are being established.

End-user policy changed.

What happens after a pen test?

After the successful completion of a pen test, an ethical hacker shares his findings with the target organization's information security team. Ethical hackers usually categorize their findings with a score based on severity, so the issues with the highest score are prioritized for remediation.

The organization uses these findings as the basis for further investigation, assessment and security remediation. Decision makers and stakeholders are also involved at this stage, and the organization's IT or security team makes deadlines to ensure that all security issues are addressed quickly.

How do I perform a pen test?

Pentesting is unique from other cybersecurity assessment methods because it can be adapted to any industry or organization. Depending on an organization's infrastructure and operations, a particular set of hacking techniques or tools may be required. These techniques and their methodologies may also vary based on IT personnel and their company standards. Using the following customizable six-step process, pen tests provide a range of results that can help organizations proactively update their measures:

Preparation. Depending on the needs of the organization, this step can be a simple or extensive procedure. If the organization has not yet decided which vulnerabilities it wants to evaluate, a significant amount of time and resources should be spent combing the system for possible access points. These in-depth processes are usually only necessary for companies that have not yet conducted a full audit of their systems. However, once a vulnerability assessment has been performed, this step becomes much easier.

Creating a plan of attack. Before an IT department hires ethical hackers, it designs a cyber attack, or list of cyber attacks, for the team to use to perform the pen test. During this step, it is also important to determine what level of system access the pentester has.

Building a team. The success of a pen test depends on the quality of the testers. This step is often used to designate the ethical hackers best suited to perform the test. These decisions can be made by companies based on the specialties of the employees. For example, if a company wants to test its cloud security, a cloud expert may be the best person to properly evaluate cyber security.

Setting the target. What does the team of ethical hackers steal? The target chosen in this step can greatly influence the tools, strategies and techniques used to obtain the necessary data.

Taking the test. This is one of the most complicated and nuanced parts of the testing process, as there are many automated tools and techniques that testers can use, including Kali Linux, Nmap, Metasploit and Wireshark.

Preparing the report. Reporting is the most important step of the process. The results provided by the testers must be detailed so the organization can integrate the findings.

What pentesting tools are there?

Pentesters use a number of tools to perform reconnaissance, detect vulnerabilities and automate certain parts of the pen test. Some of the most commonly used tools are:

Specialized control systems: Most pentesters use operating systems designed for pen testing and ethical hacking. The most popular is Kali Linux, an open-source Linux distribution that comes with pentesting tools such as Nmap, Wireshark and Metasploit.

Tools for cracking credentials: These programs can recover passwords by breaking encryptions or performing brute-force attacks, using bots or scripts to automatically generate possible passwords and test them until one works. Examples include Medusa, Hydra, Hashcat and John the Ripper.

Gate scanners: Port scanners allow remote pentesters to test devices for open and available ports, which they can use to penetrate a network. Nmap is the most commonly used port scanner, but masscan and ZMap are also common.

Vulnerability scanners: Vulnerability scanning tools search systems for known vulnerabilities, allowing pentesters to quickly find potential entries into a target. Examples include Nessus, Core Impact and Netsparker.

Web vulnerability scanners are a subset of vulnerability scanners that assess Web applications and Web sites. Examples include Burp Suite and OWASP's Zed Attack Proxy (ZAP).

Packet analyzers: packet analyzers, also called packet sniffers, allow pentesters to analyze network traffic by capturing and inspecting packets. Pentesters can find out where traffic comes from, where it goes and - in some cases - what data it contains. Wireshark and tcpdump are among the most widely used packet analyzers.

Metasploit: Metasploit is a framework for pentesting with a host of features. Most importantly, Metasploit allows pentesters to automate cyber attacks. Metasploit has a built-in library of pre-written exploit codes and payloads. Pentesters can select an exploit, give it a payload to deliver to the target system and let Metasploit handle the rest.

What is the difference between a pen test and an automated test?

Although a pen test is largely performed manually, pentesters also use automated scanning and testing tools. But they also go beyond these tools, using their knowledge of the latest attack techniques to perform more in-depth testing than a vulnerability assessment (or automated testing).

Manual pen testing

Manual pen tests uncover vulnerabilities and weaknesses that are not in popular lists (e.g.. OWASP Top 10) and tests business logic that automated tests may overlook (e.g., data validation, integrity checking). A manual pentest can also help identify false positives reported by automated tests. Because pentesters are experts who think like adversaries, they can analyze data to target their attacks and test systems and Web sites in a way that automated testing solutions that follow a scripted routine cannot.

Automated testing

Automated testing generates results faster and requires fewer specialized professionals than a fully manual pen testing process. Tools for automated testing track results automatically and can sometimes export them to a centralized reporting platform. Also, the results of manual pen testing can vary from test to test, while repeatedly running automated tests on the same system produces the same results.

What are the advantages and disadvantages of pentesting?

With the frequency and severity of security breaches increasing year after year, organizations have never needed more insight into how to resist attacks. In addition, various regulations and security standards such as the AVG and ISO 27001 require an organization to have its security tested on a regular basis. With these needs in mind, here are some pros and cons of this type of security testing.

Benefits of pentesting

Identifies weaknesses in security measures, including automated tools, configuration and coding standards, architecture analysis and other lighter forms of vulnerability assessment.

Locates both known and unknown software flaws and security vulnerabilities, including minor flaws that are not of great concern on their own, but can cause material damage as part of a complex attack pattern

Can attack any system, mimicking how most malicious hackers would behave so as to mimic a real opponent as closely as possible.

Disadvantages of pentesting

It is a time-consuming and costly process

It does not completely prevent bugs and vulnerabilities from reaching the production environment; it only provides insight to mitigate these risks

What is a pentest?