What Types of Penetration Testing Can I Conduct to Determine Security Weaknesses in My IT Infrastructure?

Pentesting (or "pentesting") is an assessment technique for testing computer systems, networks, or applications against actual attacks by simulating them in order to assess security vulnerabilities and weak points that malicious actors might exploit; its aim is to uncover these flaws so as to provide recommendations for improving overall security posture. In this article we'll look at different forms of pentesting you can employ to identify security weaknesses in your IT infrastructure as well as various approaches and use cases such as using phishing emails as pentesting tools.

What Is a Penetration Test & What Is the Purpose of Penetration Testing?

A penetration test is a planned attack on hardware, network, or software systems with intention to expose security weaknesses that may violate systems and valued data. Pentesters use this test to look at weaknesses in an IT infrastructure. These tools determine the effectiveness of security hardware and software along with cybersecurity policies. Pentests can be performed internally or externally. If the test reveals any weak spots, the tester can choose to safely exploit the weakness in the system to work on them or give a detailed report. 

What Types of Penetration Testing Can I Conduct to Find Security Weaknesses?

Penetration testing is a process used to detect and address vulnerabilities in computer systems and networks. There are various approaches for conducting penetration tests, each offering advantages and disadvantages - black box testing, white box testing and gray box testing are some popular examples - however which you choose depends on the individual needs and goals of the testing project. 

Internal / External Infrastructure Pentesting

Internal infrastructure penetration testing involves simulating an attack from within the organization's network. The objective is to evaluate the security of the internal systems, devices, and resources accessible to authorized users. During an internal penetration test, the hacker operates from within the organization’s network, either physically present on-site or by gaining network access through an authorized user account.  

External infrastructure penetration testing focuses on evaluating the security of an organization's network infrastructure from an external perspective. During an external infrastructure penetration test, the ethical hacker operates remotely. This type of testing aims to identify weaknesses in publicly accessible systems, such as web servers, firewalls, and remote access services.

Social Engineering / Phishing Testing

Social engineering is a common way for internal hackers to enter a system. This type of pentesting focuses on manipulating users to gain unauthorized access to systems, sensitive information, or confidential data. Testers can conduct remote tests using phishing emails with campaigns and physical tests. They use different types of social tactics such as intimidation, manipulation, eavesdropping, imitation, or other tactics. Phishing plays a significant role in social engineering due to how attackers manipulate and trick users into thinking they are communicating with legitimate sources. 

Wireless Network Testing

This detailed test is used to check the security of wireless devices within an organization. It’s used to target multiple devices such as laptops, smartphones, and tablets. The methodology for wireless tests are used to discover encryption weaknesses, identify all signal leaks/Wi-Fi networks, find profiles and credentials for private networks, or find weaknesses in wireless protocols, admin credentials, and wireless access points.  

Website Testing

Website testing is a type of security assessment that focuses specifically on identifying vulnerabilities and weaknesses in web applications. Web tests are used to test browsers, web applications, and their components (like Plug-ins, Applets, or ActiveX). This test examines the endpoints of website apps that users interact with regularly. 

Physical Pentesting

Physical tests help determine how easily it could be to gain an attempt or gain access to a facility. Physical testing includes motion sensors, RFID/door entry systems, lockpicking, or vending/personnel impersonation. During this type of testing, a pen tester could manipulate or deceive an employee to gain physical access to the premises. 

Cloud Penetration Testing

Cloud services are used by private users, employees, and organizations to store or back up all types of data. There are several public cloud services that are hands-off for data security, making the users or organizations take all responsibility for the security of their data. Because of the lack of data security, it may be necessary to inform the cloud service provider of the intent of a pentest. Some cloud pentests include applications/API access, poorly used passwords, encryption, poorly used firewalls, or computer security. 

Client-Side Testing

Client-Side tests are used to identify threats that happen locally. This could be a flaw in the software application that runs on the users’ workstations, which could be easy for a cybercriminal to exploit. This test includes applications or programs like browsers (Safari, Chrome, Firefox), sniffers, presentation and content creation packages (MS PowerPoint, Photoshop, Adobe Page Maker, media players), and Git clients. 

What Are the Different Approaches to Penetration Testing?

Penetration testing is a process for identifying and addressing vulnerabilities in computer systems and networks. There are several different approaches to testing, each with its own strengths and weaknesses. Some of the most common approaches include black box testing, white box testing, and gray box testing. Each approach has its own advantages and disadvantages, and the choice of approach will depend on the specific needs and goals of the testing project.

Black Box Testing

In black box testing, the tester has no prior knowledge or access to the target system or network. The tester simulates an external attacker with limited or no information about the internal infrastructure. This approach mimics a real-world scenario where an attacker has no insider knowledge. The tester starts from scratch, identifying vulnerabilities and potential entry points solely through external reconnaissance and analysis. Black box testing provides a comprehensive assessment of the organization's external security posture.

White Box Testing

In white box testing, the tester has full knowledge and access to the target system or network. The tester is provided with detailed information about the internal infrastructure, such as network diagrams, system configurations, source code, and other relevant documentation. This approach allows the tester to focus more on internal security controls, code analysis, and architecture review. White box testing provides a deeper assessment of the internal security controls and can be more effective in identifying complex vulnerabilities and misconfigurations.

Gray Box Testing

Gray box testing is the middle ground, combining elements of both black box and white box testing. In gray box testing, the tester has partial knowledge or limited access to the target system or network. They are provided with some information about the internal infrastructure, such as high-level system architecture or specific application functionalities. Gray box testing allows the tester to focus on specific areas or vulnerabilities of interest, while still simulating a partial insider's perspective. This test strikes a balance between realism and efficiency, providing a targeted assessment.

Phishing Emails as a Pentesting Tool 

Phishing emails can be used as an effective penetration testing tool to assess an organization's susceptibility to social engineering attacks and identify potential vulnerabilities within its security defenses. Utilizing phishing as an attack vector enables them to assess awareness levels regarding potential phishing threats as well as evaluate security awareness programs or filtering and detection systems.

Phishing Protection with Guardian Digital

Phishing is rapidly evolving, and traditional email security solutions like desktop protection and antivirus, which are updated retrospectively, are no longer able to provide reliable protection against today's advanced attacks.

Guardian Digital uses resources from around the world in ways no other provider can to protect its customers against the latest phishing and zero-day attacks identified worldwide. Guardian Digital EnGarde Cloud Email Security anticipates the threats specific to your users, stops them using a collection of flexible filters that adapt to your environment, and updates its protection in real-time to remain ahead of the ever-changing threats that your business faces daily. The ongoing system monitoring, maintenance and support that Guardian Digital provides offers the around-the-clock email vigilance required for the early detection and elimination of phishing attacks, while reducing the strain on businesses’ overworked IT departments, enabling them to more productively focus on tasks unrelated to email security. By preventing phishing attacks leading to security breaches, minimizing downtime, increasing productivity, and safeguarding your operations, businesses can expect to see a positive impact on their bottom line and a rapid return on investment (ROI).

Keep Reading About Phishing Protection

Penetration testing plays a vital role in improving the security and resilience of organizations' digital infrastructure. By simulating real-world attacks and identifying vulnerabilities before malicious actors can exploit them, penetration testing helps organizations proactively strengthen their defenses. Organizations gain invaluable insights into their security vulnerabilities through various tests such as network, web application, wireless, social engineering and physical. Organizations use penetration testing as a powerful weapon in their ongoing effort to secure sensitive data while upholding trust while protecting against threats in an ever-evolving digital landscape.

• Learn how to recognize and protect against phishing attacks.
• Learn why over 90% of modern cyberattacks begin with a phishing email, and how to safeguard your users and key assets.
• Learn how to improve your email security posture to defend against attacks and breaches by engaging in best practices.
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