What is Penetration Testing and How Does It Work?

A Penetration test is a legitimate simulated attack carried out on a computer system to assess its security. What are the benefits of penetration testing?

12. Apr 2023
What is Penetration Testing and How Does It Work?

A Penetration test, often known as a pen test, is a legitimate simulated attack carried out on a computer system to assess its security. To identify and illustrate the effects of system flaws on the business, penetration testers employ the same tools, strategies, and procedures as attackers. Often, penetration testing replicate different types of assaults that can endanger a company. They are able to assess a system's resilience to assaults from both authenticated and unauthenticated positions, as well as from a variety of system roles. A pen test can explore any component of a system with the correct scope.

What are the benefits of penetration testing?

In an ideal world, software and systems would have been created from the ground up to be free of harmful security defects. Pen testing provide information on the success of that goal. An organisation can benefit from pen testing. 

  • Discover systemic flaws
  • Identify the controls' robustness
  • Encourage adherence to data privacy and security laws (e.g., PCI DSS, HIPAA, GDPR)
  • Provide management-relevant qualitative and quantitative examples of the current security landscape and budget priorities.


How much access are pen testers given?

Testers are given varied levels of knowledge about or access to the target system depending on the goals of a pen test. Sometimes the pen testing team starts with one strategy and sticks with it. Sometimes, as the testing team becomes more familiar with the system during the pen test, its strategy changes. Pen test access comes in three levels.

1. Opaque Box - The target system's internal organisation is unknown to the team. It acts like a hacker would, searching for any openings that could be used outside.

2. Semi-opaque box - One or more sets of credentials are known to the team in some capacity. The target's core data structures, code, and algorithms are also known to it. Pen testers may create test cases based on intricate design documentation, such as the target system's architecture diagrams.

3. Transparent Box - Pen testers have access to systems as well as the artefacts that make up those systems, such as the source code, binaries, containers, and occasionally even the servers that host those servers. The fastest way to get the highest level of assurance is using this method.

What stages of pen testing are there?

Pen testers imitate attacks from hostile opponents. They typically follow a plan that consists of the following actions to accomplish this:

Reconnaissance - To guide the attack approach, assemble as much information as you can on the target from both public and private sources. Internet searches, the recovery of domain registration data, social engineering, nonintrusive network scanning, and occasionally even trash diving are sources. The attack surface and potential vulnerabilities of the target are mapped out by pen testers using this information. The type of reconnaissance varies depending on the goals and parameters of the pen test; it could be as straightforward as making a phone call to go through a system's features.

Scanning - Pen testers employ tools to look for flaws in the target website or system, such as open services, application security problems, and open source vulnerabilities. Depending on what they discover throughout the test and during their reconnaissance, pen testers employ a range of tools.

Gaining Access - Attacker goals may include data theft, alteration, or deletion; the transfer of funds; or even just reputational harm to a business. Pen testers choose the appropriate tools and methods for each test scenario to enter the system, whether through a vulnerability like SQL injection or through malware, social engineering, or another method.

Maintaining Access - Pen testers must maintain connectivity with the target long enough for their simulated attack to succeed once they have gained access to it in order to exfiltrate data, modify it, or exploit functionality. It is important to show the possible impact. 

What are the types of pen testing?

For the best risk management, pen testing must be approached holistically. Testing every part of your surroundings is required for this.

Web App - Testers evaluate the effectiveness of security measures and search for undiscovered flaws, attack patterns, and any other potential security holes that might allow a web app to be compromised.

Mobile App - Testers search for flaws in server-side functionality and application binaries operating on mobile devices using automated and extended manual testing. Session management, cryptography, authentication, and authorisation problems, as well as other typical online service vulnerabilities, are examples of server-side vulnerabilities.

Networks - This testing finds widespread to serious security flaws in external networks and systems. Test cases for encrypted transport protocols, SSL certificate scoping concerns, use of administrative services, and other items are on the experts' checklist.

Cloud - Traditional on-premises environments are very different from cloud infrastructures. Usually, the enterprise using the environment and the cloud services provider share responsibility for security. As a result, cloud pen testing needs a specific set of expertise and knowledge to examine the cloud's numerous components, including configurations, APIs, different databases, encryption, storage, and security measures.

Containers - Containers obtained from Docker frequently have flaws that can be widely exploited. Another frequent issue related to containers and their environment is misconfiguration. Expert pen testing can reveal both of these dangers.

Embedded devices (IoT) - Due to their longer lifespans, distant locations, power limitations, regulatory regulations, and other factors, embedded / Internet of Things (IoT) devices like watches, medical devices, and home appliances have particular software testing needs. To find the flaws that are most important to the applicable use case, experts conduct a complete communication analysis together with a client/server study.

Mobile Devices - Pen testers utilise both automatic and manual analysis to discover flaws in server-side functionality and application binaries running on mobile devices. Application binaries may contain flaws in client-side trust, authentication and authorization, incorrectly configured security controls, and cross-platform development frameworks. Session management, cryptography, authentication, and authorisation problems, as well as other typical online service vulnerabilities, can all be considered server-side vulnerabilities.

APIs - The OWASP API Security Top 10 list is covered by both automated and manual testing methods. Security threats and vulnerabilities that testers keep an eye out for include issues with user authentication, object level authorization, excessive data exposure, resource constraints, and more.

CI/CD Pipeline - The CI/CD pipeline incorporates automated and intelligent code scanning technologies as part of modern DevSecOps techniques. Automated pen testing tools can be incorporated into the CI/CD pipeline in addition to static tools that identify known vulnerabilities in order to simulate what a hacker might do in order to compromise the security of an application. Static code scanning misses latent vulnerabilities and attack patterns, which can be found through automated CI/CD pen testing.

Which pen testing tools are available?

When it comes to pen testing, there is no universal tool. Instead, various objectives call for various sets of tools to do port scanning, application scanning, Wi-Fi intrusions, or direct network penetration. The various pen testing tools can be categorised broadly into five groups.

  • Tools for reconnaissance to find open ports and network hosts.
  • Vulnerability scanners for identifying problems in web applications, APIs, and network services.
  • Man-in-the-middle proxies or specialised web proxies are examples of proxy tools.
  • Tools for system footholds or asset access through exploitation.
  • Tools used after exploitation for interacting with systems, preserving and gaining further access, and achieving attack goals.


How Pen testing are different from automated testing?

Pen testers do employ automated scanning and testing tools even though pen testing is primarily a human process. Nevertheless, they also go above and beyond the tools, utilising their expertise in the most recent attack methodologies to offer more thorough testing than a vulnerability assessment (i.e., automated testing).

Manual Pen Testing - Using manual pen testing, you can find flaws and vulnerabilities that aren't on popular lists (like the OWASP Top 10) and test business logic that automated testing could miss (e.g., data validation, integrity checks). A human pen test can also be used to find false positives that automated testing has revealed. Pen testers can examine data to target their attacks and test systems and websites in ways that automated testing solutions following a predefined routine cannot since they are professionals who think like adversaries.

Automated testing - In comparison to a fully manual pen testing approach, automated testing produces results more quickly and requires less skilled individuals. Results from automated testing are automatically tracked, and they are occasionally exportable to a centralised reporting platform. Moreover, the outcomes of manual pen tests can differ from one test to the next, whereas repeating automated testing on the same system will yield consistent outcomes.

PROS and CONS of Pen Testing

Organizations have never needed insight into their defences against assaults more, as the frequency and severity of security breaches rise year after year. To be compliant with regulations like PCI DSS and HIPAA, periodic pen testing is required. Here are some advantages and disadvantages of this kind of defect finding technique keeping these pressures in mind.

Pros of Pen Testing

  • Discovers flaws in upstream security assurance methods, including automated tools, configuration and coding standards, architecture analysis, and other less intensive vulnerability assessment operations.
  • discovers software faults and security vulnerabilities, both well-known and new, including minor defects that, by themselves, are unlikely to cause much concern but may result in real damage as part of a sophisticated attack scheme.
  • Can attack any system, emulating the behaviour of the majority of criminal hackers, and coming as near to a real-world adversary as is possible.


Cons of Pen Testing

  • Is it expensive and labor-intensive?
  • Does not completely stop bugs and defects from entering the production process.



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