How Pen Testing Works and the Importance of Conducting One

In the digital age, data breaches get more and more frequent. Even reputed large companies have had their customer’s personal information stolen, costing them millions of dollars. So how to defend yourself from data breaches? One way is to conduct regular pen tests. But what is a pen test, and why is it so important? We’ll answer those questions and more.

Pen Testing

It’s a systematic process that is used to evaluate the security of an organisation or system by simulating a real-world attack. The main goal of pen testing is to find security flaws that are at risk of being discovered by others and fix them before they become a problem. Pen tests can be conducted manually by anyone possessing a threat amount of skill and experience or they may be performed automatically with the help of tools.

Why Is Pen Testing Important?

In the current business landscape, data breaches are becoming more and more common. By conducting a pen test, you can find out if your system is vulnerable to an attack and take steps to mitigate the risks. Pen tests can also help you assess the effectiveness of your security measures and Identify areas that need improvement.

Additionally, web application pen testing can help you meet compliance requirements. Many organisations such as those falling under the government, healthcare, and finance sectors are required to conduct regular pen tests.

How Does Pen Testing Work?

Pen tests are typically conducted in three ways:

White-box pen testing: In this type of test, the testers have complete knowledge of the system and its inner workings. It helps defend against insider threats.

Black-box pen testing: This type of testing is conducted without any prior knowledge of the system or its inner workings. It is used to simulate an external threat.

Grey-box pen testing: In this type of test, the testers have partial knowledge of the system.

Conducting a Pen Test

The pen testing process usually follows these steps:

Reconnaissance: The first step is to gather information about the system, such as IP addresses, domain names, and network architecture. This information can be gathered manually or through automated tools.

Scanning: This may involve searching for open ports, weak passwords, and other vulnerabilities usually using automated tools.

Gaining access: Once the tester has found a vulnerability, they will attempt to exploit it to gain access to the system.

Maintaining access: In this step, the tester tries to maintain their access to the system and keep it undetected. They may also try to escalate their privileges within the system.

Clearing the tracks: In the final step, the tester clears all traces of their activity and restores the system to its original state.

Additionally, professional pen testing may include –

Report generation: A detailed report is generated that includes a list of all vulnerabilities found, their severity, and recommendations for remediation.

Mitigation: Once you’ve discovered all the flaws in your system, you need to fix them right away. This may involve patching holes in the system, implementing new security measures, or both.

Re-scans: After the vulnerabilities have been addressed, a re-scan is conducted to verify that they have been successfully patched.

Certification of compliance:  In some cases, the organisation may require certification to show that they have met compliance requirements.

What to Test For?

Pen tests can be conducted using various methods:

Social engineering: In this type of test, the attacker tries to trick employees into disclosing sensitive information or performing actions that may compromise security.

SQL injection: This is a code injection technique that can be used to bypass security controls and access sensitive data.

Buffer overflow: This could allow an attacker to misuse or crash a system by sending it more data than it can handle.

Denial-of-Service: Testing for DoS attacks can involve stress testing a network or flooding traffic towards the servers to make a system unavailable to legitimate users.

Cross-site-scripting: This could allow anyone to inject malicious code into the website, which would then be executed by unsuspecting users who visit the site.

These are some of the common attacks but there are several more. Testing should be tailored to the particular needs of a business. For example, a healthcare organisation may want to focus on HIPAA compliance, while a financial institution may want to focus on PCI DSS compliance.

How Often Should Pen Tests Be Conducted?

The frequency of pen tests depends on the organisation’s risk tolerance. For example, an organisation that handles sensitive customer data may want to conduct pen tests on a quarterly basis. 

On the other hand, an organisation with less sensitive data may only need to conduct pen tests on an annual basis. It is recommended that you conduct pen tests at least once a year and whenever important changes are made to your systems.


Pen testing can be a time-consuming and expensive process, but it is worth it to protect your business from data breaches. By understanding how pen testing works and what to test for, you can ensure that your organisation is as secure as possible.

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Jonathon Spire

Jonathon Spire

Tech Blogger at Jonathon Spire

My diverse background started with my computer science degree, and later progressed to building laptops and accessories. And now, for the last 7 years, I have been a social media marketing specialist and business growth consultant.

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Jonathon Spire

I blog about a range of tech topics.

For the last 7 years I have been a social media marketing specialist and business growth consultant, so I write about those the most.

Full transparency: I do review a lot of services and I try to do it as objectively as possible; I give honest feedback and only promote services I believe truly work (for which I may or may not receive a commission) – if you are a service owner and you think I have made a mistake then please let me know in the comments section.

– Jon