8 Key Steps To Successful Penetration Testing

Penetration testing, also known as “pentesting”, is a valuable tool for identifying and addressing vulnerabilities in a system or network. When performed correctly, a penetration test can help ensure the security and integrity of sensitive data.

This article will explore the key steps to successful penetration testing, including the definition and purpose of pentesting, how to perform it, and the best practices to follow.

What are pentests (penetration testing)?

Penetration testing is a simulated cyber attack on a computer system, network, or web application focused on testing defenses and finding security vulnerabilities that an attacker could exploit.

Penetration testing aims to create a vulnerability assessment, uncover security weaknesses, and leave recommendations to improve the system's defenses.

A penetration test is typically conducted by a team of security professionals who use various tools and techniques to gain unauthorized access to a target organization. This may include exploiting known vulnerabilities, using social engineering tactics to trick employees into divulging sensitive information, and bypassing security controls.

Penetration testing is an important aspect of cybersecurity, as the testing report helps organizations identify and address potential security vulnerabilities before malicious actors can exploit them.

It can also be used to validate an organization's security controls' effectiveness and demonstrate compliance with industry regulations and standards.

How to perform penetration testing

Current company computer systems consist of many layers and interconnected parts: network services, web applications, infrastructure, devices used by employees, and others. All of them need to be examined thoroughly by a security team using a defined set of penetration testing tools.

There are three main penetration testing methods we’d like to discuss, as follows:

• Black box testing- this penetration test method assumes hackers have minimal knowledge on the systems and is looking to gain access to our system through web URLs, IP addresses, or open ports.
• Gray box testing - moving one step up, gray box approaches are instances where white hat hackers are given limited insights into their target system. In this instance, penetration testers could be granted low-level accounts with some documents for their vulnerability assessment.
• White box testing - the final penetration testing method is the white box approach, where the penetration tester is given admin-level accounts to find exploitable vulnerabilities within the system.

One key thing to remember about different types of penetration tests is to check compliance requirements and mandatory practices – especially for programs that process personal data or payment methods.

8 steps to (successful) penetration testing

The penetration testing process cover everything needed to assess existing defense mechanisms and prevent future hackers from gaining access to the system. The penetration testing steps from below follow what is described in Penetration Testing Standard.

1. Pre-engagement interactions

The first step in any pentest is planning. This involves defining the scope of the test, identifying the target systems or networks, and determining the objectives of the test.

It also includes the start date of the assessment, the estimated time to complete the test, and the contact persons involved. Optionally, additional details like documentation, and previous penetration test results can be provided.

2. Intelligence gathering

The next step is to gather as much information as possible about the target systems or networks.

This can be done using a variety of penetration testing tools and techniques, including network scanning and reviewing publicly available data about the system (DNS reconnaissance, leaked credentials, code repositories, or even questions asked on StackOverflow).

As much as these vulnerabilities could be found online, target systems could also be attacked through offline means; such as documents found through the trash, onsite reconnaissance, and security equipment inspections.

Offline and onsite intelligence gathering may uncover improper sensitive data management.

3. Scanning

Once you have gathered the necessary information, the next step is to scan the target systems or networks for vulnerabilities. This is typically done using automated tools, such as vulnerability scanners, that can identify potential weaknesses in the system or network.

Typically, one could use dynamic analysis or static analysis to test how the application responds to various threats.

4. Threat modeling

After gathering enough information about the system penetration tester analysis assets, business processes, and human factors to create a threat model. This should also include an attacker perspective: who he can be and what capabilities he has.

Keep note that the model should be clearly documented, else the vulnerability assessment would prove unverifiable for future penetration tests.

5. Vulnerability analysis

Having information about the system architecture, implementation details and business processes penetration tester can start looking for potential vulnerabilities.

These can range from service misconfiguration and open ports on a remote host to insecure process design and server directories susceptible to a brute force attack. The goal of this step is to create a vulnerability assessment that has been tested, validated, and proven through research.

6. Exploitation

The next step of our penetration test is to attempt to exploit vulnerabilities that have been identified during the scanning phase. This is typically done using a combination of tools and manual techniques, such as password cracking or SQL injection.

7. Post-exploitation

After the exploitation phase, the next step is to determine the value of gathered accesses and data. This may allow penetration testers to go further into the system while maintaining access, gaining pathways to more secure documents in the system.

8. Reporting

After collecting the data, a document is created. It includes all of the agreements made before the assessment, an executive summary, details about found vulnerabilities, and recommendations to mitigate them.

Tricky moments - what to be careful about while doing pentests

While penetration testing can be a valuable tool for identifying and addressing vulnerabilities in a system or network, there are a few tricky moments to be aware of.

First, it is important to ensure that the scope of the pentest is clearly defined. This will prevent the pentesters from accidentally accessing sensitive data or disrupting the operation of the system or network.

Second, hire experienced and ethical hackers. An experienced team will help to ensure that the test is performed in a safe and controlled manner. Not only are they professionals at their craft but their experience with other projects means they have deeper industry knowledge that could go far in protecting your systems.

Third, good communication with the owner of the system, or designated contact person, can improve the pentesting execution. This is especially true in cases where the scope is very limited, or when it includes production systems.

Initial scoping may not always clearly define what should be attacked or not, which will lead to unwanted disruptions in day-to-day activities.

While penetration tests should ideally be done before a system is put into production, maintenance tests should be done discreetly and without interrupting business operations to make sure that the results are as authentic as possible.

Netguru’s best practices for the penetration tester

Our experience with pentests has left us with a checklist of items that define a successful assessment, here’s a list of our best practices to remember across all the phases of penetration testing:

Defined test scope

Clearly define the scope of the pentest. This will help to ensure that the test is focused and targeted and that it does not accidentally disrupt the operation of the system or network.

On the other hand, during scoping, it is important to include as big part of the system as possible; to not create a fake picture of overall system security.

Experience and ethics

Ensure that the pentest is carried out by experienced and ethical hackers. This will help to ensure that the test is performed in a safe and controlled manner and that any vulnerabilities that are identified are properly addressed.

Regularity of testing

Regularly perform penetration testing on your systems and networks. This will help to identify any new vulnerabilities that may have been introduced, and to ensure that your systems and networks remain secure.

Acting upon pentest report

It is important to follow up on the recommendations made in the pentest report. This will help to ensure that any vulnerabilities that are identified are properly addressed and that your systems and networks remain secure.

Preventing future collapse with the penetration test

Penetration testing is a valuable tool for identifying and addressing vulnerabilities in a system or network. By following the steps outlined in this article, and by following best practices for penetration testing, you can help to ensure the security and integrity of your sensitive data.

In addition to the steps and best practices outlined above, there are a few other key takeaways to keep in mind when it comes to successful penetration testing.

• Penetration testing is not a one-time event. To maintain the security of your operating systems and networks, you should regularly call on penetration testing services to identify and address new vulnerabilities.
• Penetration testing is not a substitute for other security measures. While pentesting can identify and address vulnerabilities, it does not replace other security measures such as firewalls, intrusion detection systems, and secure coding practices.
• Penetration testing is only as good as the pentesters who perform it. To ensure that your pentests are successful, you should work with experienced and ethical hackers knowledgeable and skilled in the latest pentesting techniques and tools.

Overall, successful penetration testing requires careful planning, skilled execution, and regular follow-up. By following the steps and best practices outlined in this article, you can help to ensure the security and integrity of your systems and networks.