Types of Penetration Testing –

ByFreda D. Cuevas

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Cyber security is now one of the biggest issues faced in today’s corporate environment. Every day, you hear about Cyber hackers and Threat actors attacking computer systems and services, stealing everything from passwords to financial information and data. The I.T department and security professionals spend countless hours implementing security measures to try to combat these types of security breaches but hackers will always find new methods to attack and new vulnerabilities in systems. By performing different types of penetration testing techniques, security professionals can assess the security of their IT infrastructure by proactively seeking and exploiting system vulnerabilities the same way an attacker would. These vulnerabilities could arise from a number of different sources, including unpatched software, coding errors, and weak or default passwords.

Whether to comply with security regulations such as ISO 27001, gain customer and 3rd party trust, or achieve your own peace of mind, penetration testing is an effective method used by modern organisations to strengthen their cyber security posture and prevent data breaches.  

The objective of a penetration test is to:

  • Identify potential breach sites and vulnerabilities
  • Simulate cyber attacks by penetrating vulnerable systems, applications, and services using both manual and automated tools
  • Gain access to sensitive data and/or systems
  • Test the compliance of security policies;
  • Verify the awareness of the staff in terms of security;
  • Check if and how an organization can face a security breach.

Before we go into the types of Pen tests available I want to briefly explain the 3 categories of Pen tests that really state the level of knowledge you expect the hacker to have of the systems in place. In a real-world Cyber-attack, the hacker probably will not know all the ins and outs of the IT infrastructure of a corporation. Because of this, he or she will launch an all-out, brute force attack against the IT infrastructure, in the hopes of trying to find a vulnerability or weakness on which they latch onto.

  • Black box tests are performed with no prior knowledge of the tested network ecosystem. A black box test is an objective assessment of security as seen from outside the network by third parties.
  • White box tests are performed with full knowledge of the internal design and structure of the tested ecosystem.
  • Grey box tests combine aspects of white and black box testing into one. For this variety of tests, experts will assess the level of software security seen by a legitimate user with an account.

Types of Penetration Testing

Let’s explore the main types of penetration testing and determine which are best for your business:

Network Penetration Testing

A network penetration test is the most common test and aims to identify weaknesses in your network infrastructure, be that on the premises or in cloud environments. The main purpose is to identify the most exposed vulnerabilities and security weaknesses in the network infrastructure (servers, firewalls, switches, routers, printers, workstations, and more) of an organization before they can be exploited.

It is recommended that both internal and external.

External penetration testing involves searching for vulnerabilities that could be exploited by an attacker that is trying to get access to your business-critical systems and data from outside of the boundaries of your network.

Check out this article, 10 network security best practices that can be used to best mitigate against malicious users and attacks on your network.

Internal penetration testing is concerned with testing your internal corporate environment to look for internal vulnerabilities. Under this simulation, a pentester assumes the role of a malicious “insider,” or an ill-intended employee with a certain level of legitimate access to the internal network. 


Social Engineering Penetration Testing

Cybercriminals know intrusion techniques have a shelf life and sitting in front of their computer and using technical techniques to penetrate systems is becoming a lot more difficult.  These malicious threat actors have turned to reliable non-technical methods like social engineering, which rely on social interaction and psychological manipulation to gain access to confidential data. Scams based on social engineering are built around how people think and act and once an attacker understands what motivates a user’s actions, they can deceive and manipulate the user effectively.  For example, if an attacker does his research and finds out that a user likes Basketball then they are more likely to have success with a basketball orientated phishing email than a Tennis.

Social engineering penetration testing is where the tester attempts to persuade or fool employees into providing sensitive information, such as a username or password. Phishing emails are a prime example of a social engineering ploy. A hacker may pose as a manager (using a very similar email address), and ask an employee to share a login or transfer money under urgency.

Physical Penetration Testing

Not all cyberattacks involve technology. Physical penetration testing simulates a physical breach of your security controls by an intruder. Assessors may pose as delivery personnel to attempt to gain access into your building, or quite literally break into your office to provide proof of real-life vulnerabilities. 

This type of penetration testing looks far beyond just physical theft and also considers sneaky threat actors, like those who may plug a malware-injecting device like a USB Ninja Cable into a computer to tap into your network.

Application Penetration Testing

As a result of the worldwide Coronavirus epidemic, organisations have been forced to extend their corporate network boundaries and allow users to be able to easily access their applications when working remotely. The prevalence of web applications in modern organizations has made this a possibility. Valuable business information that is now transmitted over the internet has made for an attractive target to cybercriminals.

Application and Web application penetration testing is used to discover vulnerabilities or security weaknesses within your applications. Web-based software, browsers, and their elements such as ActiveX, Plugins, Silverlight, Scriptlets, and Applets are common targets for a web application penetration test. Assessors look for flaws in the apps’ security protocol, including missing patches or exploited holes in externally-facing web applications, applications that run on internal networks and the applications that run on end-user devices and remote systems.

Wireless Penetration Testing

Wireless technology has revolutionised the way devices communicate with each other. Some organizations are the victims of wireless security breaches. Instead of your personal data travelling over a single cable, your data is transmitted through the open air where anyone within the given vicinity of your wireless internet connection could “eavesdrop” on the wireless traffic. A wireless network that has not been configured correctly with weak security encryption can allow an attacker to easily intercept the data and decrypt it. In a wireless penetration test, all networks should be tested, including corporate and guest networks and wireless access points, to find vulnerabilities that bad threat actors could exploit.

The Red Teaming Strategy

Most people would associate the term red teaming with a military reference whereby attackers (the red team) compete against defenders (the blue team). The term red teaming in cyber security uses the same concept whereby a red team would use a combination of the types of penetration tests outlined in this article to attack an organization’s digital & web infrastructure. Red teaming is the practice of rigorously challenging plans, policies, systems and assumptions by adopting an adversarial approach. A red team may be a contracted external party or an internal group that uses strategies to encourage an outsider perspective. Typically, engagements are performed over a longer period than other assessments – typically weeks but sometimes even months.


There are many types of penetration testing techniques, and each type can provide different insights into an organization’s security posture and defences. It is important to understand the relative risks that your organisation is facing in order to choose the most appropriate type. Over time, try to test your entire IT environment to ensure you don’t miss important security gaps and vulnerabilities, which may otherwise remain invisible.


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