What is Penetration Testing?

Penetration testing is a security test conducted by cybersecurity experts to attempt to discover vulnerabilities in the systems of an organization. Penetration tests are simulated attacks that utilize various tactics and techniques hackers would deploy. The goal is to improve the security posture of an organization. These simulated exercises offer enterprises unbiased third-party feedback on their security practices.

The rapid evolution of today’s threat landscape makes it impossible for an organization to be completely rid of vulnerabilities and risks. Regardless of how robust the security posture of an organization is, risks still exist. Failure to be aware of risk, however small, can result in an organization being expensively crippled. By incorporating penetration testing in their security and risk assessment frameworks, organizations can effectively deal with potential security risks.

Also see: Best Network Virtualization Software & Products 

Types of Penetration Tool

Penetration testers employ several tools to plan and execute penetration tests:

  • Reconnaissance tools gather information on the application or network being targeted.
  • Vulnerability scanners help testers expose vulnerabilities and configuration errors in applications.
  • Web proxy tools allow penetration testers to modify and intercept traffic between an organization’s web server and their browsers.
  • Exploitation tools let pen testers to attack an organization during a test.
  • Post-exploitation tools are used to erase traces of pen testers’ intrusion.

Also see: 7 Enterprise Networking Challenges 

Types of Penetration Testing

These pen testing methods enable penetration testers to carry out various types of  testing – so organizations are warned ahead of time. 

Network infrastructure

As one of the most common types of penetration testing, network infrastructure tests evaluate the vulnerabilities in network infrastructure and cut across servers, endpoint protection systems, network traffic, routers, network services, third-party appliances, and legacy devices.

Network penetration tests are meant to protect organizations from common network-based attacks. A network attack may be centered around internal infrastructures such as bypassing next-generation intrusion prevention systems or external infrastructure such as getting past misconfigured firewalls.

Web application

Web application penetration testing is about exposing the vulnerabilities of application programming interfaces (APIs) or web applications. These tests are much more focused, rigorous, and time-consuming compared to network tests, regardless of the overlap between networks and web applications.

A huge factor influencing the intensity of web application testing is that the popularity, complexity, and public availability of web applications today heavily contribute to the majority of the external attack surface.

The issues plaguing web applications include cross-site scripting, weak cryptography and authentication, and SQL injections among others.

Physical

Physical penetration tests focus on the physical security of an organization as they simulate the threats to an organization’s physical network infrastructure. They often involve having an attacker attempt to compromise the security using information or useful credentials and attempting to gain building access.

Successful entry by the attacker presents them with an opportunity to eavesdrop to gather information as well as plant suspicious devices in business environments to provide them with remote access to internal networks. These tests also remind organizations that a focus on digital security tools and frameworks without limiting outsider access to buildings and information in general invalidates these digital network security approaches.

Wireless

This test seeks vulnerabilities in wireless networks. It determines and exploits vulnerable wireless network configurations and deficient authentication. An attacker may target configurations, authentication, and protocols to attempt to remotely gain access to a wired network.

Wireless penetration tests can attempt to exploit corporate users who connect their devices to unprotected, open guest networks.

Social engineering

The greatest percentage of cyberattacks can be attributed to social engineering. As a result, social engineering tests provide a simulation of social engineering techniques such as phishing. Since social engineering is heavily dependent on human error and poor judgment, these tests expose how susceptible the employees of an organization are to these manipulative attacks.

Also see: Cloud is Down: Protecting Your Organization against Outages

Steps of Penetration Testing

Information gathering

In the information gathering stage, penetration testers take in information to get a better understanding of how a target organization works and its potential weaknesses. This can be an challenging step, as it involves employing hands-off resources and interacting with the target organization through network scans and enumeration.

Penetration testers utilize a variety of penetration tools and resources to gather information on the organization being tested. Testers can use tools such as internet footprints, internal footprints, search engine queries, domain name searches, tailgating, and more.

Reconnaissance

After gathering preliminary information in the previous stage, penetration testers need to carry out reconnaissance to analyze it. They can analyze not only the available information but also additional information, like network layouts, system descriptions, and more, to ensure they have additional information that would otherwise be overlooked, undiscovered, or withheld.

Carrying out reconnaissance is crucial, especially for network penetration tests.

Discovery and scanning

The discovery and scanning step involves using the information gathered in the two previous stages to highlight things like open ports and services as well as scan assets to expose vulnerabilities. A penetration tester can employ automated tools to carry out the aforementioned scan and discover weaknesses. They are capable of discovering additional devices, systems and servers, open ports on host devices, and query ports to determine the services running on these assets.

Testers can then follow this up with attempting to understand how the target systems respond to various intrusion attempts. Scanning can be in the form of static analysis, where the code of an application is examined to estimate its behavior while running. Within one sweep, static analysis tools can scan an application’s entire code. It can also be done through dynamic analysis where the code of an application is inspected in a running state. This proves to be a more practical approach to scanning as it delivers real-time insight into the performance of an application.

Vulnerability assessment

The next logical step is to carry out a vulnerability assessment to identify security gaps that could provide threat actors with access to the technology or environment subjected to the test. As crucial as it is, it should never be executed in place of a penetration test.

Exploitation

The exploitation stage has penetration testers endeavoring to see how far into an organization’s system they can go based on the vulnerabilities they highlighted and the mapping they did in the previous stages. Testers aim to reveal the potential damage of threats to an organization’s assets and often use both custom and publicly available exploit methods to try and compromise vulnerable assets.

However, this step has to be performed with care to avoid realizing adverse effects on mission-critical assets. Penetration testers should communicate a breakdown of their approach to exploits to ensure both parties are aligned and to determine the scope and extent of the intrusion.

Also see: Best IoT Platforms for Device Management

Final analysis and review

After exploitation, testers often assess how severe the vulnerabilities they identified are and their impact on other assets and networks within the organization. They work to gain as much information on compromised assets as proof of vulnerabilities while maintaining a healthy line of communication with the organization.

Reporting

An organization needs to learn after a successful penetration test. Therefore, reporting becomes arguably the most important step of a penetration test as it directs the future actions of an organization. The reporting should be comprehensive and insightful, at least covering all stages of the test, strengths and weaknesses of the security posture of the organization, vulnerabilities, and recommendations to remediate the problems highlighted.

Also see: Top Zero Trust Networking Solutions 

Benefits of Penetration Testing to Enterprises

Aside from the obvious and most important benefit of exposing vulnerabilities in the software, hardware and human resources of an organization, penetration testing offers so much more to enterprises.

Assessment of readiness against cyberattacks

Through penetration testing, organizations have a method of measuring the readiness of their security teams against cyber threats. They can assess whether these teams are efficient in the prevention and response to attacks as well as remediating issues. Organizations can thus take the right measures to not only improve their systems but also their security personnel.

Ensuring business continuity

Cyber threats threaten the survival of enterprises, as they often result in loss of revenue, loss of customers and their trust, and halted operations among others. Penetration testing brings these threats to the attention of enterprises and empowers them to better secure themselves against threats.

Building trust

The trust of various stakeholders is key to the longevity of enterprises today. As security breaches can result in the exposure of and loss of sensitive data, loss of finances and denial of critical services to customers, it should be a priority for enterprises to ensure they safeguard the trust of their stakeholders.

Penetration tests enable enterprises to assess how secure they are and constantly communicate that level of confidence in their security and safety to their stakeholders.

Compliance

Penetration testing helps enterprises identify the regulations an organization may not be compliant with and informs them on how to handle non-compliance.

Challenges of Penetration Testing

Labor and cost

Carrying out penetration tests can be costly for an organization, as they need to be carried out regularly. These tests also require organizations to considerably trust the testers to not misuse their skills, experience, and the provided access to sensitive information and assets.

Bugs and flaws

Corrupted or lost data, exposure of sensitive data, and server crashes are examples of the consequences of an ineffective penetration test. Such penetration tests may be a result of using unrealistic test conditions that inadvertently end up weakening the security posture of an organization.

Collins Ayuya
Collins Ayuya
Collins Ayuya is pursuing his Master's in Computer Science and is passionate about technology. He loves sharing his experience in Artificial Intelligence, Telecommunications, IT, and emerging technologies through his writing. He is passionate about startups, innovation, new technology, and developing new products as he is also a startup founder. Collins enjoys doing pencil and graphite art and is also a sportsman, and gamer during his downtime.

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