Penetration Testing - A Critical Must in Cybersecurity

4 min read

In the same way that untested backups mean you can't trust them to be reliable when you need to retrieve data, if you don't periodically pen test your network and IT systems, you can't trust your cybersecurity protections.

What is Pen Testing?

Penetration testing (also called pen testing or a pen test) probes networks for vulnerabilities using the same attack methods that cybercriminals use. Pen testing is the authorized use of attack methods to find and fix vulnerabilities before cyberattackers can exploit them.

Cybersecurity professionals often perform pen-testing via blue, red, and purple teams. The blue team is an organization's cybersecurity defense team, and the red team contains the attackers authorized to try to breach security during a pen test. Increasingly, the teams work closely together as a blended purple team to allow the red team members to pass on cybersecurity knowledge to the defenders in the blue team. A purple team arrangement also means that any vulnerabilities discovered can be corrected immediately.

Using external cybersecurity experts is the preferred way to perform pen testing. External pen test experts know current and emerging threats and attack vectors, as this is their full-time focus.

Using an external testing team also allows for various scenarios. The managers in the target organization can hire the testers but not inform their cybersecurity team about the testing. Some organizations alert their IT or SOC (Security Operations Center) teams, and some don't. A lack of warning about penetration tests shows if the network monitoring teams can detect intrusion attempts.

It's common for both teams to work together as a blended purple team. Doing this allows the attacking red team members to pass on cybersecurity knowledge to the defenders in the blue team in real time. This approach also allows for rapid fixing of any vulnerabilities discovered.

The pen testing methodology used in the red, blue, or purple approach typically gets broken down more via a white box, black box, and gray box grouping. In a white box attack, the pen testers have full and uncensored knowledge about the systems they are probing for vulnerabilities. A back box attack is the opposite, as the testers start without any insider knowledge of the organization's systems or defenses. The gray box approach is a mixture of these as the testers have some knowledge of the systems that they are trying to penetrate. Gray box testing often gets used to reduce the information collection time needed for testers to gather information before a pen test.

You can read a deep dive into this subject in our article: What is Pen Testing?

Why Pen Testing is Crucial

Pen testing is an essential component of any broader cyber security strategy. Some organizations look at pen testing as a box-ticking exercise that they need to do to satisfy external regulations or demonstrate to executives that they are testing security. Pen testing is much more than a box-ticking exercise, and there is often misunderstanding from those not experts in cybersecurity about what a modern pen test involves.

Modern pen tests are multi-faceted mini projects in their own right that enhance an organization's security posture. By allowing the identification and mitigation of any potential cyberattack vulnerabilities that bad actors could exploit to deploy ransomware, malware, trojans, or steal sensitive data and PPI. Regular pen tests are an investment in IT systems that will save costs over the medium and long term by preventing successful cyberattacks.

Specifically, regular pen testing delivers these crucial benefits:

Validation of existing cybersecurity provisions - you need to test the cybersecurity protections that are in place to ensure that they are adequate. The only way to do this is to have skilled pen testers try to bypass them before cybercriminals do.

Ensuring the cybersecurity of newly added applications or infrastructure - most organizations IT landscape is dynamic and changes over time. New applications are added (an especially easy task with the availability of cloud services), and new infrastructure gets added regularly. These additions increase the attack surface available to criminals. The security applied to them must be pen-tested periodically so that a new component or misconfiguration doesn't provide an attack route for bad actors. Organizations should also remove any decommissioned applications and infrastructure from the network to ensure that it doesn't become a liability due to not getting security updates.

Elimination of newly discovered threats - new threats and vulnerabilities are frequently discovered in all IT infrastructures, from servers to endpoint devices. Many of these vulnerabilities are zero-day exploits that need patching quickly. Pen testing is not an activity that you can do once to check a tick box. It needs to be periodic and planned on a regular schedule to check for any new threats that have become known since the previous pen testing.

Delivery of compliance requirements - many business sectors and regional jurisdictions have regulations that organizations must adopt. Many of these have punitive penalties for any data breaches that occur (GDPR and CCPA, for example), and others, such as PCI DSS, mandate that regular pen testing occurs.

Knowledge transfer for internal staff - external pen testers have a deep knowledge of cybersecurity and the threat landscape. They can pass on this knowledge when they work with internal staff (or external service providers) in an organization in pen testing projects. An excellent way to help maintain robust cybersecurity protection over time.

Critical Insight Penetration Testing

Critical Insight provides a comprehensive set of cybersecurity services and solutions to organizations of all sizes. These can be mixed and matched as required based on needs. Our cybersecurity as a Service wheel infographic below shows the services that Critical Insight delivers:

Penetration testing falls into the broader Application and Penetration Testing grouping on the wheel. For each subsection within this group, Critical Insight's pen testing delivers:

The Critical Insight pen testing team mimics the behavior of attackers and cybercriminals by using the same tools and methods. Sometimes the defenders are told in advance, and sometimes not, as outlined above in the blue, red, and purple teams discussion.

Social Engineering methods are a significant contributor to successful cyberattacks. Data from surveys report that 85% of criminals gain unauthorized access via human error due to social engineering techniques like phishing. Our Application and Penetration testers use social engineering techniques as a core part of their toolkit for penetration testing and web application security testing.


Periodic penetration testing is a critical part of any cybersecurity defense strategy. However, familiarity with IT systems can often lead to issues being overlooked by those who manage them day-to-day. Using skilled external testers who can bring fresh eyes to the task is the best way to do pen testing.

Critical Insight has the staff and expertise to deliver comprehensive modern pen testing and all the other skills, services, and solutions required to defend organizations of all sizes. Contact us today to discuss your needs.