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Volodymyr Klymenko, CEO, Senior QA

Sep 04, 2023 13 min read

How to Do Penetration Testing: The Ultimate Guide

This comprehensive guide explores the significance of penetration testing, providing insights into its various techniques, tools, and best practices.

How to Do Penetration Testing

In today's interconnected world, where cyber threats are rising, safeguarding digital assets has become paramount. Penetration testing helps organizations identify vulnerabilities and strengthen their defenses against potential cyber-attacks. This article will delve into penetration testing, providing a comprehensive guide for conducting practical security assessments. Whether you are an IT professional, a business owner, or simply curious about cybersecurity, this article will equip you with powerful insights on how to do penetration testing. 

What is Penetration Testing?

Penetration testing is like a security check-up for a computer system or network. Ethical hackers, who play the role of good guys, try to find weak spots like black hackers. But don't worry. They won't harm the system or organization.

Security flaws can hide in different places, like how the system is set up, how it checks if you're allowed to access it, and even how it handles business logic. Penetration testing hunts for these flaws and checks how well the current defenses work. The goal is to show how an outsider could find and use a flaw or weakness. 

This testing usually involves a mix of manual and automated testing. Ethical hackers use various tools to assess the system but only do what's allowed and defined. When they find any weaknesses, they give a detailed report with information on what they found, how serious it is, and what can be done to fix it.

Knowing how to do penetration testing empowers you to stay one step ahead to protect and safeguard sensitive data.

The Importance of Penetration Testing in Cybersecurity

In today's digital era, cyber-attacks are becoming more dangerous and frequent, putting businesses at risk. Ransomware, phishing, and web-based attacks like XSS and SQL injection are just a few examples of severe threats. That's where Penetration testing comes in. We should be aware of how does penetration testing work.

Penetration testing takes on a hacker's perspective to spot and tackle cybersecurity risks before they become problems. Unlike other tests that raise alerts, it uncovers real vulnerabilities and shows how they can impact a business. It empowers IT and security teams to strengthen defenses and prevent successful attacks.

Ethical hackers get creative and combine various attack methods to thoroughly test a company's systems. It is crucial because attackers do the same, searching for weak spots that automated tests may miss. Penetration testing helps keep businesses safe in a constantly evolving digital world. Understanding the steps involved in performing penetration testing helps organizations stay proactive in securing their digital assets.

Diverse Penetration Testing Services

In cybersecurity, we cannot underestimate the importance of penetration testing services. These services are like digital detectives, uncovering vulnerabilities and weaknesses in products (software). Let's take a closer look at some common types of these services:

Web App Penetration Testing

This service focuses on web applications, those nifty tools we use daily to access information and perform tasks online. Ethical hackers dive into the depths of web apps, searching for loopholes in data validation, authentication processes, and more. They leave no stone unturned, examining source code, databases, and back-end networks for potential threats. The three phases of this testing are reconnaissance, vulnerability discovery, and attempts to exploit the found weaknesses.

Network Penetration Testing

Networks are like intricate mazes, and ethical hackers are the explorers. Network penetration testing is about finding security vulnerabilities in the infrastructure, like firewalls, switches, and routers. They don't stop there; they also look for vulnerabilities in the devices connecting to the network. This thorough examination prevents attacks like firewall misconfigurations, man-in-the-middle assaults, and DNS hijacking. The hackers employ techniques like port scanning, system fingerprinting, virus scanning, and traffic fuzzing to ensure your network is fortified.

API Penetration Testing

APIs may sound technical, but they are the magic behind modern IT systems. They allow information systems to communicate and share data, making them an enticing target for cyber threats. Ethical hackers dive into APIs, learning their structures and commands. Armed with tools like OpenAPI, they uncover security issues like weak authentication, code injection vulnerabilities, and data leaks. This way, they help prevent potential breaches in the data exchange process. You can also familiarize yourself with our API testing services.

Mobile App Penetration Testing

Mobile app security becomes paramount in a world where "Bring Your Own Device" policies are popular. Ethical hackers don their virtual detective hats to identify new attack vectors that can exploit personal devices connected to organizational networks. They guard against malware distribution through mobile apps, phishing attacks targeting personal devices, and vulnerabilities in Wi-Fi networks. Uncovering these risks assists in safeguarding your mobile environment from potential exploitation.

In the ever-evolving cybersecurity field, penetration testing is vital in protecting your digital assets. Web apps, networks, APIs, and mobile devices are all potential entry points for cyber threats, but with the help of cybersecurity experts, you can build a strong fortress of defense. Use the power of diverse penetration testing to ensure you stay one step ahead of cybercriminals and protect your data and reputation. Using the knowledge of how does penetration testing work can strengthen defenses and protect valuable data.

Types of Penetration Testing Techniques: The Secrets of Ethical Hacking

Penetration testing is aimed at assessing the resilience of a company's digital defenses. Not all Penetration tests are the same; their approach and effectiveness can vary depending on the project's scope and desired outcomes. Knowing how to do penetration testing allows security teams to simulate real-world cyberattacks, testing the robustness of their security measures. 

Let's delve into some different techniques used for penetration testing. 

Black Box 

Picture this - an ethical hacker stepping into a world of darkness, armed with little to no prior information about the company's IT infrastructure or security. Welcome to the world of Black Box testing, also known as External Penetration testing. The tester simulates a real cyberattack in this method, starting outside the network's boundaries. With no insider knowledge about existing security measures, these tests aim to identify vulnerabilities as an actual hacker would. However, being blindfolded in the simulated attack makes Black Box tests time-consuming, but they provide valuable insights into a company's external defense.

White Box 

In contrast, White Box testing is like being handed a treasure map with all the clues. Here, the tester has complete network infrastructure and security systems knowledge. Having such insider information, the tester can comprehensively assess the organization's defenses. While White Box tests may not mimic external cyberattacks, they are highly effective in identifying vulnerabilities within the network. They can even simulate the risk of insider threats, mirroring the potential impact of an attack from within the organization. With transparency guiding the process, White Box testing allows quicker completion, although larger enterprises may still have to wait for detailed results.

But that's not all! Beyond the common types of pen testing, let's unravel some additional categories that help organizations choose the most suitable tests for their specific needs.

Gray Box

Gray Box testing represents the best of both worlds - a mix of the Black Box and White Box techniques. Testers are granted partial access or knowledge about the company's network. This method is advantageous when evaluating specific public-facing applications with a private server backend. Armed with this combined information, testers can attempt to exploit specific services to gain unauthorized access to other parts of the network. While Gray Box tests may take less time than Black Box tests due to partial knowledge, they still require more time than White Box tests due to limited access.

External Test

This technique targets information assets visible to outsiders, such as websites, apps, DNS servers, and email systems. The objective may range from data extraction to executing unauthorized transactions. By conducting external tests, organizations can identify vulnerabilities exposed to external attackers, allowing them to enhance their security measures proactively.

Internal Test

In this approach, the focus shifts to launching attacks from within the organization's network. It seeks to assess the potential damage internal threats, including malicious insiders and employees susceptible to phishing and social engineering, can cause. Uncovering internal vulnerabilities empowers organizations to address potential weaknesses before they are exploited.

Blind Test

In a blind test, the penetration tester operates with publicly available information about the target. They do not know the target's security posture. It mimics the scenario of an attacker with limited prior knowledge attempting to breach the target. The target company is informed before the test's occurrence, allowing them to prepare and assess their defenses.

Double-Blind Test 

This technique takes the element of surprise to another level. Neither the penetration tester nor the target organization know about the test. Both sides must rely solely on their resources and skills to outwit one another. The penetration tester employs available tools and expertise to breach the target's defenses, while the target must utilize its capabilities to prevent unauthorized access.

The choice of technique depends on the specific needs of the organization and the nature of the systems being evaluated. By understanding the intricacies of Black Box, White Box, and Gray Box testing, organizations can proactively safeguard their digital assets against the ever-evolving world of cyber threats. So, whether navigating in the dark, basking in the light, or exploring the shades of gray, penetration testing stays on safeguarding to ensure digital resilience.

Main Steps of Penetration Testing

Penetration testing is like a friendly hacker's mission to find security weaknesses. Let's break down the steps connected with today's main topic, how to do penetration testing:

1. Planning: The penetration tester sets goals and gathers information, sometimes using sneaky tactics like social engineering.

2. Scanning: Analyzing the system to find weak spots and potential entry points. Technical tools help with vulnerability scans.

3. Burrowing: How deep can the penetration tester go? They search for valuable data and try to stay hidden, installing backdoors for future access.

4. Analyzing: A thorough review and reporting of test results, looking for ways to improve security. Like detectives, they imagine how an attacker might try to cover their tracks.

Penetration testing is like being a virtual spy. We plan, scan, breach, burrow, and analyze to protect devices from cyber threats. Stay one step ahead with penetration testing! You can also learn about web application security testing that can help protect your web applications against potential cyber threats and vulnerabilities.

Penetration Testing Tools

Penetration testers seek out vulnerabilities in systems and networks to enhance security. They rely on a toolkit of automated tools to aid them in their mission, each with its unique purpose. Let'sexplore how to perform a penetration testingwith the help of tools in simpler terms:

Port Scanner

A port scanner is a tool or software used to scan and analyze the open ports on a computer, server, or network device. It helps identify which ports are active and listening for incoming connections. The scanner sends requests to specific ports and analyzes the responses to determine whether a port is open, closed, or filtered.

Network Sniffer

Consider it a spy intercepting secret messages in the network traffic. This tool monitors data flow, spotting suspicious activities and identifying the source, device, and protocol, aiding network penetration testing.

Web Proxy

Picture it as a sneaky trickster tampering with messages between browsers and web servers. Testers use this tool to spot hidden weaknesses like form fields, which attackers could exploit for cross-site scripting and request forgery attacks.

Password Cracker

This tool cracks password hashes like a lock picker. It helps testers check if weak passwords are being used, preventing unauthorized access to the target network.

Penetration testers wield a powerful arsenal of automated tools to identifysecurity vulnerabilities. These digital detectives employ their toolkit to safeguard your systems, ensuring they stand firm against potential cyber threats. Mastering how to perform a penetration test involves a combination of techniques and tools to uncover hidden weaknesses and ensure the resilience of your digital assets. Use the power of automation and secure your digital fortress today! Are you looking for reliable test automation services to streamline your testing process? Or are you in the fintech industry and require specialized fintech testing services? You're in the right place. Let us help you enhance the efficiency and effectiveness of your testing efforts, ensuring the success and integrity of your software products.

Penetration Testing vs. Vulnerability Scanning

Both penetration testing and vulnerability scanning serve the purpose of pinpointing weaknesses in an organization's security strategy.

A vulnerability scanning involves an automated examination of your network and systems to identify known weaknesses. Their potential risk and exposure levels categorize the outcomes. Usually, these findings are evaluated by either your service provider or a security expert to confirm their accuracy. Vulnerability scanning relies heavily on automation and can be done regularly to monitor your network's security continuously.

On the other hand, penetration testing takes a more hands-on, manual approach, delving deep to discover complex or hidden vulnerabilities that automated tools might miss.

Consider vulnerability scanning as a handy helper for repetitive tasks, ensuring everything stays consistent and saving valuable time. It's excellent at pointing out publicly known vulnerabilities and reminding teams to update their applications and apply patches.

In contrast, penetration tests are more like skilled detectives, thinking outside the box and mapping out potential attack scenarios. They uncover weaknesses like complex code injections, sneaky XXS attacks, and social engineering vulnerabilities.

The significant difference lies in the tools used. Vulnerability scanning relies on automated tools for quick assessments, while penetration testing encompasses diverse security tools. Penetration testers may use specialized ethical hacking platforms and custom tools to investigate threats like Python or Java-specific vulnerabilities. However, mastering these tools can be time-consuming, and they might only sometimes be readily available.

So, when identifying security weak points, vulnerability scanning is the speedster, but penetration testing is the inquisitive detective who uncovers hidden secrets. Both have their roles in keeping your organization secure from cyber threats.

Optimizing Penetration Testing for Maximum Security

The process includes emulating a range of attack scenarios to measure the system's ability to withstand cyber threats and prevent data breaches. To get the most out of penetration tests, organizations can follow these essential best practices:


Defining the Scope: With limited testing budgets, it's crucial to define the scope of tests wisely. Focus on critical and high-risk areas of the network and applications. Code-intensive applications, for instance, may be prime targets for penetration testing due to their increased risk.


Identifying and Prioritizing Risks: Pinpoint areas with higher application security risks. These may include vulnerabilities in operating systems, application code, and configuration files. Addressing these issues can prevent potential attacks and data breaches.


Incorporating Diverse Data Sources: Protect valuable assets like financial and customer data through thorough penetration tests. It ensures regulatory compliance and assesses the security of connecting software.


Preparation: Before testing, organizations must be well-prepared. Understand the types of tests supported by the cloud vendor, create a responsive team to review test results, and schedule automated patches after each test.

These best practices can enhance the security strategy and build secure defenses against potential cyber threats. Penetration testing becomes a proactive approach, uncovering vulnerabilities and ensuring a safer digital environment. 


Penetration testing is an indispensable practice for fortifying your organization's cybersecurity posture. You can effectively detect and mitigate potential vulnerabilities by understanding how to perform a penetration test and utilizing appropriate tools.

Cybersecurity is an ongoing effort, and regular penetration testing is vital to stay ahead of evolving threats. With the knowledge gained from this article, you can safeguard your digital assets and keep your network secure from malicious acts. If you have a specific idea you'd like to discuss or want guidance on your project, feel free to share it with us. Contact us to get started!

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Frequently Asked Questions

What is penetration testing and why is it important?

Penetration testing is a security assessment that uncovers vulnerabilities in systems and networks. It helps strengthen defenses against cyber threats.

How does penetration testing work?

Ethical hackers simulate cyberattacks to find weaknesses in a system's setup, authentication, and data handling. They provide detailed reports on vulnerabilities and how to fix them.

What are the different types of penetration testing?

There are various techniques, including Black Box, White Box, and Gray Box testing. Each offers a unique perspective on vulnerabilities within a network.

What tools are used in penetration testing?

Tools like Port Scanners, Network Sniffers, Web Proxies, and Password Crackers aid penetration testers in identifying vulnerabilities and enhancing security.

What's the difference between penetration testing and vulnerability scanning?

Penetration testing involves manual testing to uncover complex vulnerabilities, while vulnerability scanning relies on automated tools to identify known weaknesses.

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