Penetration Testing in 2023: A Beginners Guide

7 minute read
February 8, 2023
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Cybersecurity is becoming more and more important in today’s world as technology advances and more sensitive information is stored online. One way to ensure the safety of your information is by performing a penetration test, also known as ethical hacking.

If you’re new to the world of cybersecurity, the idea of penetration testing may seem overwhelming. However, it’s actually a relatively straightforward process that can help protect your information and keep it secure.

Hacking scenes in movies are often portrayed inaccurately, with characters typing furiously on keyboards and hacking into complex systems in a matter of seconds. In reality, hacking is a slow and meticulous process that requires a great deal of technical knowledge and skill, and it is far from the glamorous and action-packed portrayal that is often depicted in these scenes; usually with script writers that have no IT experience whatsoever, a perfect example of this the clip below:

The Most Accurate Hacking Scene Ever
From “Castle” Season 8 Episode 8. Copyright ABC.

So, what exactly is a penetration test and how does it work?

A penetration test is essentially a simulated attack on a computer system, network, or web application to identify vulnerabilities that could be exploited by real attackers. The purpose of this test is to identify weaknesses in the system before they can be taken advantage of.

Automated vs Manual Testing

Pros of Automated Penetration TestingCons of Automated Penetration Testing
Faster and more efficientMay miss certain types of vulnerabilities that require a human touch
Can test a large number of systems in a short amount of timeDependent on software updates and patches
Can identify certain types of vulnerabilities, such as those related to software configurationLimited ability to identify non-technical vulnerabilities
Can be run regularly to identify new vulnerabilitiesMay generate a high number of false positives
Pros of Manual Penetration TestingCons of Manual Penetration Testing
Can identify non-technical vulnerabilitiesSlower and less efficient than automated testing
Can find vulnerabilities that automated tools may missDependent on the expertise and experience of the tester
Can provide a more comprehensive view of the target environmentCan be time-consuming and costly
Can provide in-depth analysis and recommendations for remediationLimited ability to test a large number of systems in a short amount of time

Penetration testing can be performed in several ways, including manual testing, automated testing, and a combination of both. Manual testing involves a human tester manually exploring the target system and attempting to identify vulnerabilities, whereas automated testing relies on software tools to perform the same task.

Automated testing can be very effective in identifying certain types of vulnerabilities, such as those related to software configuration, but it can also miss other types of vulnerabilities that require a human touch. As a result, many organisations opt to use a combination of manual and automated testing to get a more comprehensive picture of their security posture.

All the Steps

Step 1: Understanding the Scope of the Test

The first step in conducting a penetration test is to understand the scope of the test.

his includes determining the specific objectives of the test, the systems and applications that will be tested, and the level of access that will be granted to the testers. The scope should also specify any limitations or restrictions that will be imposed during the testing process, such as time constraints or legal requirements.

Understanding the scope of the test helps to ensure that the test is focused and effective, and that it covers all relevant aspects of the target system.

Step 2: Research and Information Gathering

Once you have a clear understanding of the scope of the test, the second step in the penetration testing process is research and information gathering. This involves collecting information about the target system, including its network architecture, software applications, and user accounts.

This information can be obtained through various means, such as public sources, vulnerability databases, and direct reconnaissance of the target system. This step is crucial in determining the potential attack vectors that could be used against the target system, and in planning the testing methodology.

Step 3: Conducting the Test

With the research complete, it’s time to start the actual penetration test.

This involves using the information gathered in the previous step to launch a simulated attack on the target system. The objective of this step is to identify and exploit any vulnerabilities or weaknesses in the target, and to gain unauthorised access or cause damage to the system.

Pen testers use a variety of tools and techniques, including network scans, vulnerability assessments, and exploitation frameworks, to conduct the test.

Step 4: Analysing the Results and Creating a Report

Once the test is complete, the final step in a penetration test is to analyse the results of the test and create a report.

This involves evaluating the impact of the simulated attack, documenting the vulnerabilities and weaknesses identified during the test, and making recommendations for improving the security of the target system. The report should be comprehensive and provide detailed information on the testing methodology, the results of the test, and the recommended solutions for addressing the identified vulnerabilities.

This final step is critical because it provides the target with the information needed to take action to improve the security of their systems and protect against future attacks.

What tools should I use?

With the four major steps covered, let’s look at the main types of tools that are used in both steps 2 & 3.

Vulnerability Scanners

One of the most significant tools in a penetration tester’s toolkit is a vulnerability scanner. A vulnerability scanner is a software programme that automatically detects vulnerabilities in a target system by sending specially crafted packets and analysing the responses. Some of the most popular vulnerability scanners include Nessus, OpenVAS, and Qualys. These tools can quickly identify a wide range of vulnerabilities, including those related to software configuration, missing patches, and misconfigured network services.

Network Mapping

Another crucial tool in the penetration tester’s toolkit is a network mapping tool. A network mapping tool is utilised to create a map of a target network, including the systems, services, and network topology. This information is vital for penetration testers, as it provides a clear understanding of the target environment and the systems and services that need to be tested. Some of the most popular network mapping tools include Nmap and Angry IP Scanner.

Exploitation Tools

In addition to vulnerability scanners and network mapping tools, penetration testers also rely on exploitation tools to carry out specific types of attacks. Exploitation tools are designed to take advantage of vulnerabilities in a target system, such as exploiting a flaw in a web application to gain unauthorised access to sensitive data. Some of the most popular exploitation tools include Metasploit, Canvas, and Core Impact.

Specific Software

In terms of specific tools you should use, the answer lies largely with what you are testing, but here is a list of the top 20 tools (2 OS + 18 Software tools) used worldwide and their brief descriptions:

What’s to come from Penetration Testing in 2023?

Penetration testing in 2023 will continue to be an important tool for organisations to evaluate their security posture. As cyber threats become more sophisticated, it is crucial for organisations to adopt a proactive approach to security, which includes regular penetration testing.

AI & Machine Learning vs Penetration Testing

One of the key trends in 2023 will be the increasing use of artificial intelligence and machine learning in penetration testing.

HAL 9000: "I'm sorry Dave, I'm afraid I can't do that"

Okay, AI is nothing like HAL 9000, however, automated tools will and are becoming more advanced, allowing organisations to conduct large-scale tests in a shorter amount of time. However, while automated testing is highly effective in identifying certain types of vulnerabilities, it may miss other types of vulnerabilities that require a human touch.

As a result, many organisations will continue to use a combination of manual and automated testing to get a more comprehensive view of their security posture.

Cloud Computing

Another trend to watch in 2023 is the increasing use of cloud computing. As more organisations move their systems and data to the cloud, it is crucial that they assess the security of these systems. Penetration testing can help organisations identify any vulnerabilities in their cloud infrastructure and ensure that their security systems are equipped to handle the challenges posed by the cloud.

Concluding Notes

Penetration testing is a crucial component of a comprehensive security programme, as it provides organisations with the information they require to enhance their defences against real-world threats.

It is important to note that pen-testing is only part of a mature security routine, and it must be accompanied with the correct policies, data security, incident response plans, etc. You can learn more about this on our post here: So, You wanna get into Cyber Security? | This is an IT Support Group

The best tools for conducting a penetration test will vary depending on the specific needs of the organisation, but a combination of manual testing, automated testing, vulnerability scanners, network mapping tools, and exploitation tools are all critical components of a comprehensive penetration testing programme.

By leveraging these tools and techniques, organisations can gain a deeper understanding of their security posture and take the necessary steps to improve their defences against malicious entities, especially as we see the rise in cyber attacks quickly accelerating with hybrid wars, unstable financial markets and much more this year.

Keep finding your vulnerabilities before someone else does.