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Penetration Testing – Here's Everything You Should Know About It

Adrian Marszalek 74580312c1

10/02/2022 |

12 min read

Adrian Marszałek

Businesses must use a comprehensive approach to foolproof their systems. There are numerous standardized security methods available. Let's look at one of the most common: penetration testing.


Table of contents:

  1. Penetration testing – definition
  2. Penetration testing – what does it mean for business?
  3. Common pentesting strategies and tools
  4. Pentesting – the bottom line


Penetration testing – definition

Penetration testing (also known as "white-hat hacking" or "pen testing") is a simulated cyberattack on a company's system program or physical means of access restriction (such as gates, elevators, and card readers) to identify exploitable security flaws. 

So-called ethical hackers use penetration testing tools to check for software, network, and website vulnerabilities, ensuring that potential weaknesses are identified and patched before real-life attackers exploit them. In other words, white-hat hacking is a legal way of breaking in by purposely breaching security with the mindset of an attacker.

For the purpose of thoroughly testing expected behaviors and procedures protecting the company's confidential data, a variety of break-in scenarios are conducted. In every scenario, the system's configuration vulnerabilities are examined through a series of software and hardware attacks. What's important here is that it's done thoroughly on a fully functional system (manually or automatically) but usually in a controlled environment (i.e., on a non-production database) so the actual service can still stay operational.

As there is always room for improvement, allowing for an ethical hack into your own business should be viewed as an opportunity to improve existing processes, thus achieving higher resilience. And to provide results even faster, fully automated pen-testing should be performed under the supervision of expert testers. 

Penetration testing – what does it mean for business?

The complexity of software applications and the fact that they are connected to billions of devices via the internet make them vulnerable to security threats. Moreover, organizations with large amounts of data may be susceptible to being exploited by intruders who gain access to critical data, causing them to lose customers and money. 

To secure consumer data, businesses must ensure that their networks are up to date and protected against malicious activity. Because of the widespread availability of the internet worldwide, hackers from every part of the globe can easily infiltrate an organization's system unethically and compromise their security controls to achieve their harmful goals.

As previously stated, penetration testing is a specialized technique that allows organizations to test their security protocols, so they can address any loopholes before they become real-life problems. Businesses may suffer financial losses as well as customer churn if an intruder gains access to and steals critical data. To avoid such losses, ethical hacking employs a variety of techniques, enabling businesses to:

  • Detect the weaknesses in their systems
  • Test new security protocols
  • Improve their security policies
  • Increase employees’ vigilance

To put it another way, penetration testing aids organizations in risk management, data breach protection, and business continuity. It helps businesses answer the question, "Is my data easy to steal?" which is especially important in highly regulated industries like banking and healthcare. Plus, data breaches are costly. According to IBM, the average cost of a data breach in the United States is $4.24 million!

Common pen testing strategies and tools

Most businesses prefer to skip the right to selecting a proper testing strategy and budget assessment. Yet, it’s critical to understand the fundamentals of pen-testing requirements to achieve fully trusted results.


The five R's rule of pen testing

When a company plans to perform penetration testing in a controlled environment, the requirements must be realistic and dependable. The ethical hacker will simulate a real-world scenario where the system could be compromised. As a result, employees' privacy rights must be considered before engaging in this activity.

Before pen-testing can begin, the following five requirements must be met:

  • Respect: During pen-testing, everyone involved with the system should be treated with dignity and should not be pressured or made to feel uneasy.
  • Restriction: People must behave normally, with no deviation from how they usually act in their daily lives.
  • Reliable: Pen-testing should be dependable without interfering with the company's regular operations.
  • Repetition: Pen-testing is repeated multiple times to achieve precise results. The results should be stable as long as the environment remains constant.
  • Reportable: It is critical to monitor and improve the process to be more effective in the future. Every significant action should be recorded in a log, and test results should be organized in a meaningful order to aid decision-making.

After you've mastered those rules, it's time to select the best strategy for your particular type of business software.


Main strategies of penetration testing

Overall, penetration tests are divided into three categories:

Black-box testing

The closest scenario to a real-life scenario is black-box testing, in which the penetration tester is given only restriction lists and general test boundaries, with no valuable hints on the infrastructure, software, or security measures to be tested. Within the time allotted for preparation, the penetration tester is entirely free to gather information, prepare, and select tools.

Gray-box testing

A gray-box test evaluates a network's security in a more targeted manner. This type of test imitates hackers who do not waste time identifying vulnerabilities, are more knowledgeable about the data they seek and know exactly where to look. These assessments can be useful in combating advanced threats to a specific part of the software infrastructure, but they also limit feedback on overall security performance.

Gray-box testers frequently assume the identity of someone with administrative privileges and access to the system. They are taught the fundamentals of the system's complexity, architecture, documentation, and design.

White-box testing

White-box testing (also known as "logic-driven testing," "auxiliary testing," "open-box testing," and "clear-box testing") is a type of cross-sectional testing in which all information is disclosed to a penetration tester. The actual testing is based on addressing all of the vulnerabilities in the system and its behaviors after patching one by one.

Because white-box penetration testers have the same level of knowledge as developers, both teams can collaborate to ensure the security of a system. In contrast to black-box testing, hackers have complete access to all source code and architecture documentation. Despite its advantages, this type of testing does not assess the critical factor in the vast majority of real-world attacks – the human factor – because all of the information is already widely available to the penetration tester and there is no need to actually break into any systems.

We can distinguish five general services based on the three basic types of testing, which address a variety of requirements for web applications or software:

  • External penetration testing focuses on assets that are publicly accessible, such as websites, web applications, DNS, and emails. These tests are designed to determine whether or not hackers can gain access to and extract data from external systems.
  • Internal evaluation. An internal penetration test simulates a malicious insider attack on a company's systems. This method of pen-testing can also be used to screen employees for vulnerabilities to external social engineering or phishing attacks that steal their credentials.
  • Testing in the dark. A pen-tester, acting in the role of an actual hacker, attempts to break into a system using only publicly available information. What is critical is that the target organization is informed of when and how the pen-tester will attack. A blind test is adequate for assessing vulnerability, but it is not as informative as the following double-blind test.
  • Double-blind evaluation. A double-blind penetration test is one in which neither the pen tester nor the target is aware of the scope. Security personnel are unaware of a simulated attack. This prevents them from over-hardening their defenses and demonstrates where they need to improve. Because security personnel are not prepared to deal with pen testers, they must rely on processes and strategies.
  • Purpose-driven testing. Purpose-driven testing aims to identify and implement the best information security strategies. The movements of the tester and the security team are communicated to one another. This provides the entire pen test team with valuable real-time hacker feedback.


What are the main phases of penetration testing?

Penetration testing is a highly technical process in practice. Let’s make ourselves familiar with the  main phases of penetration tests you may have come across:


This is the stage of the test where data for the attack is gathered – typically through the use of social engineering. During this phase, the hacker verifies the correct domain, the number of subdomains linked to the parent's domain, and whether or not a firewall is configured for the specific server.


The tester can determine which services and ports on the server are open. The system is being examined to see how it will respond to the attack; testers look for vulnerabilities and access points. They frequently use technical tools to help with this process.

Weaponization & delivery

In this phase, the tester uses cross-site scripting, SQL injection, backdoors, or other techniques to figure out how to get around the firewall and into the system. They then gain access to the system, take over the network or devices, and steal data.

Command & control

The penetration tester then determines how long they can stay in the system, what data is compromised, and how deep they can go. They try to maintain access for as long as possible by installing rootkits and backdoors.


The final phase of the test includes pen testers mimicking how a hacker would conceal their tracks in order to erase evidence of a cyberattack. Then, they provide an in-depth report that summarizes their findings on any exploitable vulnerabilities. Based on the provided list of all steps, commands, tools, and outputs produced by the systems, this will serve as a foundation for the internal IT team to implement necessary changes. 

In addition, a shorter executive-level report with key takeaways from the test and general recommendations is being prepared. The organization should take precautions to ensure that reports do not end up in the hands of the wrong people, treating it as working instructions on how to breach their own security. 

Pen tests, like network security testing, assess a company's incident response capabilities or readiness to respond to an attack. The results of the tests must be effective enough to recommend reducing potential vulnerabilities and eliminating those discovered during the testing process. To put it simply, the more practice a company gets, the better it will be at dealing with a real-life incident. 


Tools for penetration testing

A single device cannot assist an organization in achieving its goal, but a collection of tools can help them identify flaws in its system. Here are just a few examples of the numerous tools available on the market:

  • Nmap is a free and open-source tool that allows experts to scan a system for vulnerabilities. NMAP is typically used to determine which devices are connected to a specific system, scan ports to decide whether or not they are open or closed, and detect loopholes.
  • Sqlmap is an open-source tool for automating SQL injection detection and exploitation. It can crack passwords and run arbitrary code commands. It supports six SQL injection techniques and allows you to connect directly to a database without the injection.
  • Metasploit is an essential framework for penetration testing. This tool can be used to create, test, and exploit system code. It is available as open-source as well as commercially.
  • Zed Attack Proxy (ZAP) can do passive scanning or simulate attacks on applications to find security flaws. It detects open ports, performs brute force searches on files or directories, crawls to learn about a site's structure, and provides random inputs (fuzzing) to see if the website crashes or behaves unexpectedly.

It is common for ethical hackers to use the same tools as black-hat (criminal) hackers.

Pentesting – the bottom line

We live in a digital age where more and more data is stored online. Regrettably, as more sensitive data becomes available, so does the number of cybercriminals and cyberattacks. Demand for penetration testers is expected to rise in the coming years in an effort to mitigate this effect. This is already noticeable, as an increasing number of businesses are realizing that penetration testing is a critical practice for ensuring a company's security.

This method can protect organizations from a variety of consequences of an attack on their businesses, such as monetary losses, brand reputation, compliance with statute rules and regulations, risk elimination, and so on. You should be aware, however, that penetration testing takes time and that rushing it can leave the system vulnerable to attack. When organizations are under time constraints, they frequently cut corners during the testing phase, putting undue strain on the team. Never put your own business's safety in jeopardy for the sake of time.

Keep in mind that pen testers will attempt to breach your security on multiple levels during the “attack.” Sending simulated phishing emails, requesting specific information, or "confirming" a log-in from your employers are all examples of this. Some testers will try to steal account credentials or network log-ins from you, or they will convince your team to download malicious software, which may result in ransom demands. This is required and should be taken seriously, just as it is with real hackers.

A resilient company is always ready for potential threats. To successfully monitor them, you should conduct pen tests regularly as part of an organization's security policy to improve system stability. And remember, it's always better to be safe than sorry!

Rated: 5.0 / 2 opinions
Adrian Marszalek 74580312c1

Adrian Marszałek

Cybersecurity geek specializing in offensive cybersecurity (penetration testing) as well as physical penetration testing (controlled non-destructive break-ins into premises). In spare time amateur wildlife photographer.

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