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Everything You Need to Know About Conducting a Penetration Test

Updated: Jan 16

Cybersecurity Services - Cybersecurity Guides

Has your business conducted a Penetration Test this year? Most Cybersecurity frameworks and regulatory standards require a test be conducted at least once per year. Historically, businesses only focused on conducting an external test to confirm that the firewall and any other externally facing devices or services are securely configured, but given the increase and advancement of security threats, an internal test must be conducted within the organization as well.

Every Cyber Insurance questionnaire (DDQ) that we have seen asks if annual internal and external tests are being conducted. If they're not, the business faces a sharp increase in their insurance premiums.


Penetration Testing Guidelines

Let's take a step back and first cover what a Penetration is and why it's important.

The goal of Penetration Testing is to validate the effectiveness and resiliency of an organization's network and its assets by using white-hat or ethical hacker techniques to identify and exploit weaknesses of security controls (including people, processes, and technology), and simulating the common objectives and actions of a potential attacker.

There are several benefits to conducting penetration tests, including:

  1. Identifying vulnerabilities - Pen tests can identify vulnerabilities in a system that may not have been detected by other security measures, such as antivirus software or firewalls. This can help organizations prioritize their efforts to secure their systems and prevent attacks.

  2. Evaluating the effectiveness of security measures - Pen tests can help organizations determine the effectiveness of their security measures. By simulating an attack and measuring the system's response, organizations can identify areas where their security measures are weak and need to be strengthened.

  3. Improving incident response capabilities - Pen tests can help organizations identify and address weaknesses in their incident response plans. By simulating an attack and testing the organization's response, organizations can identify areas for improvement and make necessary changes to their incident response processes.

  4. Demonstrating compliance - Some industries have regulatory requirements for conducting regular security assessments, including penetration tests. By conducting regular pen tests, organizations can demonstrate compliance with these requirements and protect themselves from regulatory fines and other penalties.

  5. Providing assurance to stakeholders - Conducting penetration tests can help organizations build confidence and trust with stakeholders, such as customers, investors, and regulators. By demonstrating that they are proactively addressing security risks and vulnerabilities, organizations can build confidence and trust with their stakeholders.

There are several steps involved in conducting a penetration test. These steps include:

  1. Planning - Planning is an important step in the pen testing process. During the planning phase, the tester will define the scope of the test, identify the resources that will be used, and establish the goals and objectives of the test.

  2. Reconnaissance - During the reconnaissance phase, the tester will gather as much information as possible about the system or network being tested. This may include gathering publicly available information, such as company information, network diagrams, and system configurations.

  3. Scanning - During the scanning phase, the tester will use automated tools and manual techniques to identify vulnerabilities in the system or network. These tools and techniques may include port scanners, vulnerability scanners, and other specialized software.

  4. Exploitation - During the exploitation phase, the tester will attempt to exploit any vulnerabilities that have been identified. This may include attempting to gain unauthorized access to the system or network, or to escalate privileges within the system.

  5. Reporting - After the exploitation phase, the tester will prepare a report detailing the findings of the test. This report should include a detailed analysis of the vulnerabilities that were identified, as well as recommendations for addressing those vulnerabilities.

There are three main types of Penetration Tests.

  1. Black Box Testing - Simulates an attempted hack that comes from outside of the organization. The test begins with the pen tester receiving NO information about the organization’s networks or systems.