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In 2021, cyber security attacks were at an all-time high. From data breaches to notorious ransomware, cyber-attacks have impacted companies of all sizes in the US and other parts of the world. While there are many ways to mitigate the risk, one proven strategy is penetration testing.

Big and small companies alike can improve their cyber security through penetration testing. It’s something more and more executives are looking into to safeguard networks, data, and digital assets.

With hackers getting better at their game, it’s clear that enterprises need to be a step ahead of them if they want to avoid security attacks.

What is Penetration Testing?

Penetration testing or pen testing is the practice of testing security vulnerabilities in IT systems. It’s a form of ethical hacking that helps identify loopholes in the system and infrastructure, so they can be fixed before an actual attacker takes advantage of the vulnerabilities.

Pen testing can be applied to anything within an organization’s IT ecosystem. All aspects are tested, from the code to network setting to user behavior, to see if and how much infiltration is plausible.

The process is carried out by penetration testers who design a pen test strategy and use sophisticated tools to carry out the tests in stages.

Penetration testing can also help evaluate new security measures and protocols to ensure that they do exactly what they are designed and tasked to do. It doesn’t just end at finding and exploiting one vulnerability, as testers can proceed to find even more vulnerabilities through the exploits to see how far they can get in terms of access.

At its core, pen-testing aims to strengthen cyber security in the face of threats. While it’s essentially hacking, you’re doing it yourself to find important information. That’s why it’s considered ethical hacking.

Penetration Testing Stages

Pen testing isn’t just about using a fancy tool to try to infiltrate. The process requires much more attention to detail, which is why it’s carried out in multiple stages.

There are even industry standards that dictate the pen testing methodology and stages. The most commonly used standard comes from the Open Web Application Security Project (OWASP) called the Penetration Testing Execution Standard (PTES). It comprises seven phases:

  • Pre-engagement Interactions
  • Intelligence Gathering
  • Threat Modeling
  • Vulnerability Analysis
  • Exploitation
  • Post Exploitation
  • Reporting

The PTES also provides a detailed guide and framework, which includes the major areas to be tested.

Generally speaking, there are six stages of pen testing:

  • Planning: This is the preparation stage where the testers and the company determines exactly what will be tested, how it will be tested, and what information they need to begin. Think of it as creating a roadmap of the testing.
  • Discovery: This stage involves gathering information to initiate the attack attempt. It could be something like the name, date of birth, or contact number of a person who works at the company.
  • Penetration: This is the main stage of pen testing where testers try to infiltrate security barriers. It’s the crux of the whole process and takes long, as testers go through different tests, trying to penetrate different parts of the IT infrastructure (websites, local networks, applications, third-party software, operating systems, servers, etc.).
  • Reporting: After the testing is complete, the tester analyzes the test results and creates a comprehensive report about the flaws of security they have detected by successful penetration. The report also includes the recommendations for fixing the weaknesses discovered.
  • Clean-Up: This stage requires going back into the system to clean any traces of the attacks, so no real attackers can take advantage of any leftover code or commands. This usually goes hand in hand with the remediation efforts.
  • Remediation and Retesting: After the remediations have been made, the pen testers again to see if the fixes applied are actually working.

Why Perform Pen Testing?

Pen testing requires resources, which many companies, especially small or medium-sized businesses, may not have readily available. In most cases, they have to use pen testing providers, which, of course, costs money.

So why go through all the trouble and add this expenditure? There are several benefits of pen testing:

It Helps Identify Security Risks

Pen testing is a surefire way of finding the weaknesses in your IT systems. Regardless of the kind of business you are, the niche you serve, and the technology you use, it just takes one loose end for a hacker to infiltrate and do irreversible damage.

Believe it or not, 95 percent of cyber security breaches result from human error. This just goes to show that a strong digital security policy and the latest technology are not enough. You need to test the barriers you have in place.

It can also help you prioritize the risks that pose the highest threat. Yes, pen testing can reveal multiple security risks.

It Helps Fix Vulnerabilities

Pen testing doesn’t just tell you the ‘what’; it also tells you the ‘why’ and ‘how.’ In other words, effective pen testing can provide highly detailed information about system weaknesses, which can help you understand how to fix the issue.

It Helps Improve Security Strategy

For larger enterprises that have dedicated cyber security teams, pen testing can validate their scheme. Whatever security strategy and contingency plans you have in place can also be tested through pen-testing.

It doesn’t leave the effectiveness of the strategy to assumptions or estimation. Instead, it gives real-time data about how an attacker can infiltrate, which allows you to tweak your cyber security strategy for now and for the future.

It Helps Ensure Compliance

Companies are increasingly coming under fire for weaker security protocols. After a data breach, the last thing you want is a heavy fine from a regulatory authority.

For instance, if you operate in the EU, you’re liable to comply with the General Data Protection Regulation (GDPR) for preserving data privacy. If your company’s security measures are audited, and any non-compliance is detected, you could be facing fines.

There are similar regulations in some US states that leave no room for non-compliance.

Other regulations include CMMC, HIPAA, HEOA, NERC, PCI DSS, and SOX.

Types of Penetration Testing

You may want to test everything for security vulnerabilities, but that may not suit every business. It’s best to go with the type of pen testing that best suits your company’s needs. Choosing a particular type allows testers to go pretty deep into a particular section of technology.

Here are the different types of pen testing:

Web Application Penetration Testing

Web application pen testing focuses on the security risks of any web application associated with the company in any capacity. From authorizations to code correctness to database injection, all aspects of the web applications are tested to find weaknesses.

Network Security Penetration Testing

Network security is often the biggest priority for enterprises, as network vulnerabilities can result in unauthorized access and data breaches. In this type of testing, the testers focus on the network and all the hardware and software within it. They also test passwords, configurations, and firewalls.

Cloud Penetration Testing

This type of penetration testing is for cloud providers or vendors who use a cloud provider. These tests look for security vulnerabilities in the cloud deployment as well as the applications. This way, cloud security can be strengthened even further.

Social Engineering Testing

This type of pen testing allows testers to see how end users may be exploited to gain access to the system. For example, phishing scams have recently increased, with as many as 80 percent of companies experiencing increasing phishing attacks.

Pen testers can use tools that emulate such attacks to allow companies to protect themselves and their customers.

How to Perform Penetration Testing?

You may be able to perform pen-testing on your depending on the technology and expertise you have. Some tests are rather simple, but you need a dedicated team of pen testers equipped with the right tools for a more holistic testing approach.

The tools are important because they can automate the process. That, in turn, produces reports faster, and you can prioritize and remediate risks accordingly.

This is why many organizations, especially those with multi-level and expansive IT infrastructure, go for third-party penetration testing services, which conduct tests on their behalf.

Pen testing can also be performed as a team exercise with mainly two teams: red team and blue team. The red team acts as the attackers while the blue team acts as the defenders, much like a sports match.

This allows companies to emulate real-life and real-time attacks, which gives them even more expertise in preventing attacks.


Penetration testing is a viable way to test the security of your IT systems and find weaknesses, technical or human-caused. Pen testing can test different parts of the system in great detail. Since it’s such a sensitive process for any company, it only makes sense to go with a trusted company.

If you’re a business in the San Diego area and looking to enhance your security and data protection provisions, Skyline IT Services can handle everything for you. With the best San Diego IT Support, Skyline allows businesses to focus on more important decisions while it takes care of their IT needs, including security.