What Is Penetration Testing and How Does It Work?

Penetration testing is about improving an organization’s network security by exploiting vulnerabilities.

A good penetration test is reflected by extensive details on vulnerabilities discovered, their CVVS scores, technical briefs on posed risks, influence on business, difficulty in exploitation, and strategic approach to addressing vulnerabilities.

Security teams are contented when they can identify and prioritize software risks, mitigate vulnerabilities, get proactive when tackling security, increase confidence and awareness in security strategies, meet compliance requirements, and assert that the systems they oversee run effectively. Penetration testing is a key player in enhancing robust security.

With multiple penetration testing techniques, almost every technology domain is covered. This includes web applications, cloud, blockchain, servers, API endpoints, networks, mobile devices, and wireless networks, among others.

Key questions in this field are: what is penetration testing, how does it work, and how would you benefit from it? This article breaks down the penetration testing process. You’ll also discover the need for penetration testing before launching a SaaS and learn a few tools you can use. Let’s learn, shall we?

What is Penetration Testing?

Penetration testing was inspired by the need to understand an attacker’s thought process. Even with the first security test in 1971, the field has evolved. But only then did the US Air Force have their first security testing. By the 1990s, a paper had been released documenting how to improve your site by breaking into it.

Fast forward to the 2000s, the Open Web Application Security Project (OWASP) released a testing guide on best practices. This, in turn, would be a solid foundation of today’s penetration testing and would evolve into an important feature in the software development life cycle.

As systems and software technologies evolve across many fronts, keeping up with security protocols and developing efficient systems is necessary; that’s the problem solved through pen testing.

Simply put, penetration testing entails breaking into a computer system by leveraging weaknesses and vulnerabilities. But most importantly, it’s done in a controlled environment. By simulating attacks, security teams use tools, techniques, and processes to showcase the impact of weaknesses in your business.

When done within the right scope, penetration tests look into many aspects of your system, including resilience to attacks from authenticated, unauthenticated positions and the efficacy of other system roles.

Whether on cloud, on-premises, working with APIs, managing databases, or building software as a service (SaaS), there’s always a penetration test based on your needs.

The best pen tests will be natural to your workflow and the systems involved. If you’re having trouble choosing, here’s a breakdown of the available types of penetration tests and when to use each. And now, we’ll break down how to approach penetration tests.

Breaking Down the Penetration Testing Process

The penetration testing process is procedural. It can be generalized into three phases. First is pre-engagement, where you define objectives and research about the system to be tested.

The second is engagement, which targets the system, collects data, and analyzes findings to uncover exploitation routes—lastly, post engagement, where reports are generated and actions taken to resolve vulnerabilities. Let’s dive into each stage.

#1. Reconnaissance

As a leading step, the goal of this phase is to collect as much data as possible, which, in turn, dictates effective attack methods. The information gathered includes details about the operating system, network topology, applications, user accounts, and all other relevant information.

Armed with this interest, a reconnaissance can either be active or passive. If passive, the reconnaissance sources information from publicly available resources, and when it’s active, the tester has to interact with the system. For the best results, you should use both.

To assemble network information, you can use tools like Metasploit. Here’s our open-source intelligence tools (OSINT) checklist if you want more options. These tools scan public IP addresses, index their header responses, and enlighten the tester about a network, even without actively scanning it.

The OSINT Framework shows how vast open-source resources can be used to collect data. Reconnaissance is common in internal and external pen tests.

#2. Vulnerability Assessment

Next, you scan the system to see all open ports or possible entry points. Scans are optional in penetration testing and can be done independently, called vulnerability scanning.

Remember, the data acquired from reconnaissance and scanning helps develop tests to reveal common and uncommon weak points. Such tests include SQL injection, cross-site scripting, malware, and social engineering.

The tests aim to exploit the system by escalating privileges and traffic interception while targeting high-value assets like networks, employee data, vendors, apps, partners/supply chain data, and vendor info.

Testers leverage resources like the National Vulnerability Database to find system weaknesses if the process is automated. If it’s manual, vulnerability assessment tools such as Metasploit, Commix, and Sn1per.

#3. Exploitation

Having consolidated all vulnerabilities and interpreted results from assessments, the tester exploits vulnerabilities in the target system. The process entails using tools like Metasploit to simulate real-world attacks.

Occasionally, manual techniques, human foreknowledge, and their backgrounds are used. Exploitation could escalate to data breaching, disrupting services, or accessing unauthorized information. But, care needs to be taken not to damage the system. This circles back to the scope of testing, which guides the overall process.

This stage aims to evaluate the persistence of vulnerabilities in the system and whether it leads bad actors to deep access. So, you’re emulating advanced persistent threats that could be left in a system to steal data even after months.

Records are kept to note the total time spent in a system without being caught – they showcase an organization’s effectiveness in its approach to security.

#4. Reporting

Often, many organizations skip this step. However, it is just as crucial with two major tasks. First, the tester needs to clean up the system. As a result, the system is reverted to its original state before the penetration test.

Second, the tester must review, document the susceptibilities, and elaborate on tactics used. An explanation needs to be presented to explain the exploit’s results on high-value targets. Now that the pen test is near the end, the report developed here guides fixing and improving the security posture.

Remember, a helpful report will give a general test overview and technical details. The technical information should include technical risks, influence on the organization’s business, CVVS scores, and a tactical guide to addressing the pinpointed vulnerabilities.

Benefits of Penetration Tests

Penetration tests have many benefits for your organization. It exposes vulnerabilities in your system for all tech stacks and operating systems. By screening the system designs, you can acknowledge your system’s strengths. This, in turn, allows you to focus on weak areas.

Moreover, it pinpoints security techniques that haven’t paid off. With this knowledge, the best practices can be utilized when building future/additional systems.

By implementing positive and negative tests, you can generate comprehensive reports. In this case, reports allow you to know what techniques work instead of addressing and leaving a specific problem at that.

Authentic simulation of real-world attacks provides insights into step-by-step approaches that hackers would take to exploit your system. This exposes you to tactics and time frames depicting your security posture.

Regarding compliance, penetration testing helps you gauge if your organization meets all regulations. If not, you can shape the business trajectory to be fully compliant. That aside, a penetration test can certify that your business data is secure. When this is not the case, you’re alerted and thus can take corrective action.

When allocating security budgets, penetration testing will point you to the sections that need fixing. Through thorough testing and documentation, you can establish a consistent security budget to match your needs.

Pen tests will also provide you with a new perspective on your system. This entails fixing bugs and improving the overall system design and architecture moving forward.

Additionally, pen tests can elevate customer loyalty and trust towards your brand. By providing positive results from a pen test or providing updates on resolved issues, you can present your organization/product professionally and enhance customer relationships.

Customers, when assured about the security of their services, will refer you to their friends, growing your business naturally.

Why Pen Test is Crucial Before Launching Any SaaS, eCommerce

SaaS and eCommerce are unique from other types of software. They are dynamic and adapt to ever-evolving customer needs. Besides storing vast data levels and transmitting them, they are competitive with the need for innovation and iteration of new functionalities.

Constant developments in the software present avenues for new vulnerabilities. Penetration test helps bridge the gap between innovation and security. As cyber-attacks rise, there’s an inevitable need for a proactive approach to protecting your software.

All SaaS and eCommerce need to ratify that their applications and digital products are built on secure infrastructure layers, following the best practices. Understanding the health of your digital products eradicates the chances of data breaches.

Since penetration testing combines the use of humans and machine intelligence, IT teams can leverage this knowledge to develop in-depth strategies for strengthening software security.

Pen tests can drive adaptation in software. By understanding the nature of vulnerabilities in your SaaS or eCommerce, you can modify your developmental approach and avoid introducing them in the future. This is helpful when developing multiple SaaS solutions using the same technologies and processes.

So far, you’ve been learning about penetration testing and its relevance in the software industry. As you narrow down to picking the right solutions for your toolbox, here are a few known for their best performance in the domain.

I haven’t ranked them in any order. But rest assured, they’ll save you the time you’d spend looking.

#1. Kali Linux

Kali Linux is an open-source platform targeted at security tasks like penetration testing, reverse engineering, computer forensics, and security research.

Whether you are on the cloud, containers, mobile devices, or a window subsystem for Linux, a version of Kali will always be available.

It allows you to install any pen test tools on it, although you’ll configure the tools manually. The good thing is that Kali has a vibrant community and thorough documentation to suit both veterans and novice users.

#2. Metasploit

The Metasploit framework is brought to life by a collaboration of security enthusiasts, envisioned with the goal of raising security awareness, fixing vulnerabilities, and managing security assessments.

Check out Metasploit’s GitHub for the latest guidelines on getting started, using it for security testing, and contributing to the project.

#3. Nmap

With Nmap (Network Mapper), you can explore networks and audit their security states. While it’s designed to scan large networks swiftly, it works well with single hosts.

Besides addressing security vulnerabilities, you can use it to perform repetitive tasks such as network inventory, monitoring hosts’ uptime, and scheduling/managing service upgrades.

Bringing It All Together

Penetration testing is all about improving the security of digital products by exposing vulnerabilities, showcasing how they can be exploited, giving a rundown on the potential impact on business, and providing tactical strategies to solve the said concerns.

To ensure you get the best out of penetration tests, each stage needs to be covered severely. This means treating all stages of the test with equal importance without overlooking any. Start by planning the goals of your test, and collect as much information as you need before moving forward to scanning.

Once you have scanned your systems and analyzed them fully, proceed to an attack and see how long it’d take your system to discover a breach. Check on the impact on the system, document the overall process, and ensure you draft a resolution strategy. And as you complete the test, restore systems and clean them up. Remember, pen tests should be done frequently to stay updated.

In terms of benefits, pen tests will expose vulnerabilities, strengthen your security posture, save on budgets as you can plan based on past experiences, and reshape your future system designs.

From the customer’s perspective, pen tests will help you enhance trust and build a loyal relationship. Of course, people want to work with brands that they can trust, especially in a landscape of digital currencies.

For a detailed dive into penetration testing, check out the penetration testing phases, where we break down all steps, explain the relevance of each stage, and give you a step-by-step, guided interaction with the topic.