Penetration Testing Explained

Penetration or Pen Testing Explained


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A Penetration Test (Pen Test) is an authorised simulated attack performed on a computer system to evaluate its security. Penetration testers use the same tools, techniques, and processes as attackers to find and demonstrate the business impacts of weaknesses in a system, in which a security professional simulates an attack with the permission of the  cyber system’s owner. 

The purpose of this simulated attack is to identify any weak spots in a system’s defences which attackers could take advantage of and cyber-attack the system. It is a vital process that aids in evaluating an application’s security through hacker-style exploitation to expose and assess security risks. 

As security risks can often change and be present in various areas such as system configuration, setting and login methods, it is very important to regularly do Penetration or Pen Testing. Penetration tests usually simulate a variety of attacks that could threaten a business. They can examine whether a system is robust enough to withstand attacks from authenticated and unauthenticated positions, as well as a range of system roles. 
With the right scope, a pen test can dive into any aspect of a system.

Don’t let the word “simulate” fool you: A penetration tester, or pen tester, will bring all the tools and techniques of real-world attackers to bear on the target system. 

But instead of using the information they uncover or the control they gain for their own personal enrichment, they report their findings to the target systems’ owners so that their security can be improved.Because a pen tester follows the same standard procedures as a malicious hacker, penetration testing is sometimes referred to as ethical hacking or white hat hacking; in the early days of penetration testing, many of its practitioners got their start as malicious hackers before going legit, though that is somewhat less common today. 

Penetration testing can be carried out by teams or individual hackers, who might be in-house employees at the target company, or may work independently or for security firms that provide specialised penetration testing services. You might also encounter the term red team or red teaming, derived from the name given to the team playing the “enemy” in war game scenarios played out by the military. 

It’s best to have a pen test performed by someone with little-to-no prior knowledge of how the system is secured because they may be able to expose blind spots missed by the developers who built the system. For this reason, outside contractors are usually brought in to perform the tests. These contractors are often referred to as ‘ethical hackers’ since they are being hired to hack into a system with permission and for the purpose of increasing security.

Organisations Need Frequent Pen Testing

Penetration testing is ideally to be carried out by any and every organisation that has a cyber presence, namely as websites or in the form of data storage in a cloud platform. This includes everything from startups to SMEs, SaaS companies, e-commerce sites, healthcare organisations, financial institutions like banks, government and private companies, and even educational institutions. 

Regular penetration testing of one’s cyber-facing assets can help in the timely identification of vulnerabilities before they are exploited by malicious attackers. 

The cyber threat landscape is in a constant state of flux. New vulnerabilities are discovered and exploited regularly, some of them are publicly recognised, and some are not. Being alert is the best thing you can do. Pen test goes beyond just detecting common vulnerabilities with the help of automated tools and finds out more complex security issues like business logic errors like issues related to payment gateways, Excessive Trust in Client-Side Controls, Flawed Assumptions About User behaviour, etc. It helps you get a clearer picture of your organisation’s security posture and fix the issues to harden your security.

The primary purpose of penetration testing is performed is:  

•    Keeping up with the changing cyber threat landscape.

•    Detecting and mitigating business logic errors.

•    Preparing for compliance audits.

•    Protecting your business’s reputation by stopping security breaches. 

Benefits Of Penetration Testing

Penetration Testing team provides a real-life snapshot of your security controls' effectiveness.  
In a Pen test, a security engineer finds security vulnerabilities in the application, network, or system, and helps you fix them before attackers get wind of these issues and exploit them. Pen testing is a non-negotiable fundamental step for any application or business owner. 

Ideally, software and systems were designed from the start with the aim of eliminating dangerous security flaws. A pen test provides insight into how well that aim was achieved. Pen testing can help an organisation:

•    Find weaknesses in systems.

•    Determine the robustness of controls.

•    Support compliance with data privacy and security regulations.

•    Provide qualitative and quantitative examples of current security posture & budget priorities.

Importance Of Penetration Testing

Penetration testing one’s assets is important for the following reasons:

Identification of Vulnerabilities:   Penetration testing helps identify vulnerabilities in computer systems, networks, and applications that can be exploited by attackers. This allows organisations to prioritise and fix these vulnerabilities before they can be exploited.

Enhanced Security:   Penetration testing helps organisations to enhance their security posture by identifying potential security gaps and improving their security controls.

Meeting Compliance Requirements:   Many regulatory and industry standards require regular penetration testing to ensure that organisations meet their security requirements. For example, the Payment Card Industry Data Security Standard (PCI DSS) requires regular penetration testing of networks and applications that process credit card data.

Cost-Effective:   Penetration testing helps identify potential security threats in a cost-effective manner, as it allows organisations to identify and fix security issues before they become major security incidents.
These are just a few of the reasons that make penetration testing a valuable process in the continued maintenance of asset security.

How Does A Penetration Test Work?

In a broad sense, a penetration test works in exactly the same way that a real attempt to breach an organisation’s systems would. The pen testers begin by examining and fingerprinting the hosts, ports, and network services associated with the target organisation. 

They will then research potential vulnerabilities in this attack surface, and that research might suggest further, more detailed probes into the target system. Eventually, they’ll attempt to breach their target’s perimeter and get access to protected data or gain control of their systems. 

The details can vary and there are different types of penetration tests, and we’ll discuss the variations in the next section, but it’s important to note first that the exact type of test conducted and the scope of the simulated attack needs to be agreed upon in advance between the testers and the target organisation. 

A penetration test that successfully breaches an organisation’s important systems or data can cause a great deal of resentment or embarrassment amongst that organisation’s IT or security leadership. 

There have been occasions when a target organisations has claimed that pen testers overstepped their bounds or broke into systems with high-value data they weren’t authorised to test, and threaten legal action as a result. For this reason, establishing in advance the ground rules of what a particular penetration test is going to cover is an important part of determining how the test is going to work.

Types Of Penetration Testing

There are several key decisions that will determine the shape of your penetration test. 

  • An external penetration test simulates what you might imagine as a typical hacker scenario, with an outsider probing into the target organisation’s perimeter defences to try to find weaknesses to exploit.
  • An internal test, by contrast, shows what an attacker who’s already inside the network, a disgruntled employee, a contractor with nefarious intentions, or a superstar hacker who gets past the perimeter, would be capable of doing.
  • A blind test simulates a “real” attack from the attacker’s end. The pen tester is not given any information about the organisation’s network or systems, forcing them to rely on information that is either publicly available or that they can glean with their own skills.
  • A double-blind test also simulates a real attack at the target organisation’s end, but in this type of engagement the fact that a penetration test is being conducted is kept secret from IT and security staff to ensure that the company’s typical security posture is tested.
  •  A targeted test, sometimes called a lights-turned-on test, involves both the pen testers and the target’s IT playing out a simulated “war game” in a specific scenario focusing on a specific aspect of the network infrastructure. 

A targeted test generally requires less time or effort than the other options but doesn’t provide as complete a picture.

Penetration Testing Jobs

The fact that there are so many pen testing firms should be a clue that pen testers are in high demand and there are good jobs out there for qualified candidates. These jobs aren’t just at standalone security firms - many big tech companies like Microsoft have an in-house penetration testing team. 

The two career tracks have many skills in common, but vulnerability analysts focus on finding holes in the security of applications and systems while they’re still in development or before they’re deployed, while pen testers probe active systems.    

The ethical hacking industry was founded by hackers who had once been less than ethical looking for a path to a mainstream and legal way for them to make money from their skills and this first generation of pen testers were largely self-taught. 

One of the best ways to show that you’ve been cultivating pen testing skills is to get one of several widely accepted certifications in the field. 

  • Penetration Testing Training and Certification.
  • Certifications are a key measure you can look for when evaluating whether a vendor has the experience needed to effectively assess your network. 
  • Although a minimum level of certification is important, a team with a variety of certifications amongst its members could be most capable at tackling an array of testing scenarios.

Testing areas include network infrastructure, web applications, mobile applications, wireless networks, IoT, social engineering and more.  Penetration testing is now a common subject in computer science or IT college curricula and online courses alike, and many hiring managers will expect some formal training when considering a candidate.

References

CSO Online   |    Synopsis   |    Imperva 

Getastra   |      NCSC   |     DOI.Gov

Cloudfalre   |    Wikipedia   |    Core Security

Image: Allison Saeng

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