What Is Penetration Testing and How Does It Improve Network Security? | #linux | #linuxsecurity

When setting up a new security system, you need to make sure it works properly with as few vulnerabilities as possible. Where digital assets worth thousands of dollars are involved, you can’t afford to learn from your mistakes and only fill in gaps in your security that hackers previously exploited.

The best way to improve and guarantee your network’s security is by continuously testing it, looking for flaws to fix.

What Is Penetration Testing?

So what is a pen test?

Penetration testing, also known as pen testing, is a staged cybersecurity attack that mimics an actual security incident. The simulated attack can target one or multiple parts of your security system, looking for weak points a malicious hacker could exploit.

What sets it apart from an actual cyber attack is that the person doing it is a white-hat—or ethical—hacker that you hire. They have the skills to penetrate your defenses without the malicious intent of their black-hat counterparts.

Types of Pentests

There are various examples of pentests depending on the type of attack the ethical hacker launches, the information they get beforehand, and limitations set by their employee.

A single pentest can be one, or a combination, of the primary pentest types, which include:

Insider Pentest

An insider or internal pentest simulates an insider cyberattack, where a malicious hacker poses as a legitimate employee and gains access to the company’s internal network.

This relies on finding internal security flaws like access privileges and network monitoring, rather than external ones like firewall, antivirus, and endpoint protection.

Outsider Pentest

As the name suggests, this type of pentest doesn’t give the hacker any access to the company’s internal network or employees. It leaves them the option of hacking in through the company’s external tech like public websites and open communication ports.

Outsider pentests can overlap with social engineering pentests, where the hacker tricks and manipulates an employee into granting them access to the company’s internal network, past its external protection.

Data-Driven Pentest

With a data-driven pentest, the hacker is provided with security information and data about their target. This simulates an attack of a former employee or someone who obtained leaked security data.

Blind Pentest

Contrary to a data-driven test, a blind test means the hacker gets no information whatsoever about their target other than their name and what’s publicly available.

Double-Blind Pentest

In addition to testing the company’s digital security measures (hardware and software), this test includes its security and IT staff as well. In this staged attack, no one in the company is aware of the pentest, forcing them to react as if they’re encountering a malicious cyberattack.

This provides valuable data on the company’s overall security and the staff’s readiness and how the two interact.

How Penetration Testing Works

Similar to malicious attacks, ethical hacking needs careful planning. There are multiple steps the ethical hacker needs to follow to ensure a successful pentest that yields valuable insights. Here’s an insight into pentest methodology.

1. Gathering Information and Planning

Whether it’s a blind or data-driven pentest, the hacker first needs to gather information on their target in one location and plan the point of attack around it.

2. Vulnerability Evaluation

The second step is to scan their avenue of attack, looking for gaps and vulnerabilities to exploit. The hacker seeks access points then runs multiple small-scale tests to see how the security system reacts.

3. Exploiting Vulnerabilities

After finding the right entry points, the hacker will try to penetrate its security and access the network.

This is the actual ‘hacking’ step in which they use every way possible to bypass security protocols, firewalls, and monitoring systems. They could use methods like SQL injections, social engineering attacks, or cross-site scripting.

4. Maintaining Covert Access

Most modern cybersecurity defense systems rely on detection as much as protection. In order for the attack to be successful, the hacker needs to stay inside the network undetected long enough to achieve their goal, whether it’s leaking data, corrupting systems or files, or installing malware.

5. Reporting, Analyzing, and Repairing

After the attack concludes—successful or not—the hacker will report to their employer with their findings. Security professionals then analyze the data of the attack, compare it to what their monitoring systems report, and implement the proper modifications to improve their security.

6. Rinse and Repeat

There’s often a sixth step where companies test the improvements they made to their security system by staging another penetration test. They may hire the same ethical-hacker if they want to test data-driven attacks or another one for a blind pentest.

Ethical hacking isn’t a skills-only profession. Most ethical hackers use specialized OSes and software to make their work easier and avoid manual mistakes, giving each pentest their all.

So what do pen testing hackers use? Here are a few examples.

Parrot Security OS

Parrot Security is a Linux-based OS that was designed for penetration testing and vulnerability assessments. It’s cloud-friendly, easy to use, and supports various open source pentest software.

Live Hacking OS

Also a Linux OS, Live Hacking is a pentester’s go-to as it’s lightweight and doesn’t have high hardware requirements. It also comes pre-packed with tools and software for penetration testing and ethical hacking.


Nmap is an open source intelligence (OSINT) tool that monitors a network and collects and analyzes data about devices’ hosts and servers, making it valuable for black-, gray-, and white-hat hackers alike.

It’s also cross-platform and works with Linux, Windows, and macOS, so is ideal for the beginner ethical hacker.


WebShag is also an OSINT tool. It’s a system auditing tool that scans HTTPS and HTTP protocols and collects relative data and information. It’s used by ethical hackers performing outsider pentests through public websites.

Where To Go for Penetration Testing

Pen testing your own network isn’t your best option as you likely have extensive knowledge of it, making it harder to think outside the box and find hidden vulnerabilities. You should either hire an independent ethical hacker or the services of a company that offers pen testing.

Still, hiring an outsider to hack into your network can be very risky, especially if you’re providing them with security information or insider access. This is why you should stick to trusted 3rd party providers. Here’s a small sample of those available.


HackerOne is a San Francisco-based company that provides penetration testing, vulnerability assessment, and protocol compliance testing services.


Located in Texas, ScienceSoft offers vulnerability assessments, pen testing, compliance testing, and infrastructure auditing services.


Based in Atlanta, Georgia, Raxis offers valuable services from pen testing and security code review to incident response training, vulnerability assessments, and social engineering preventive training.

Making the Most Out of Penetration Testing

While it’s still relatively new, pen testing offers unique insights into the workings of a hacker’s brain when they’re attacking. It’s valuable information that even the most skilled cybersecurity professionals can’t provide working on the surface.

Pen testing can be the only way to avoid getting targeted by black-hat hackers and suffering the consequences.

Image Credit: Unsplash.

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