How to Perform a Network Penetration Test
March 07, 2024

Dotan Nahum
Check Point Software Technologies

Sometimes, the most effective method of protection is to put yourself in the attacker's shoes so you can stay one step ahead of their next move. The same is true for penetration testing — If you can't beat 'em, join 'em.

A Collaborative Effort for Comprehensive Pentesting

Network penetration testing is a critical cybersecurity practice where ethical hackers simulate cyberattacks to identify and address vulnerabilities in a network. It involves a trio of talented cybersecurity professionals:

Red Team: Penetration testing performed by the Red Team is designed to mimic the actions of external attackers. Rather than exploiting as many vulnerabilities as possible, a red-term tests how the organization responds to real-world threat scenarios.

Blue Team: The Blue Team maintains the organization's security posture and analyzes the vulnerabilities uncovered by the Red Team, patches security holes, enhances monitoring systems, and improves incident response procedures.

Purple Team: The Purple Team, as a collaborative effort, plays a vital role in ensuring the effectiveness of penetration tests and guiding the execution. They facilitate communication between the Red and Blue Teams, helping to turn the findings from penetration testing into actionable insights and improved defenses.

Similarly, there are three types of testing:

White box: The tester has full knowledge and access to the internal structure, design, and implementation of the software or system being tested. Therefore, white box testing sees vulnerabilities that gray and black box testing doesn't.

Black box: The tester has no knowledge of the system's internal workings. They test the system from an external perspective, focusing on inputs and outputs to see how it responds to expected and unexpected actions and how quickly.

Gray box: This hybrid approach lies between white box and black box testing. The tester has partial knowledge of the internal structures and workings of the system, so the test is unbiased and reflects real attack scenarios.

5 Steps to Perform a Network Penetration Test

1. Planning and Scope Definition

Before taking even one step forward, it's vital to determine three key perimeters:

Objectives: Clearly define what the test aims to achieve. For example, identifying vulnerabilities, testing incident response capabilities, or verifying security controls.

Scope: Determine the boundaries of the test. Decide on the systems, networks, and applications to be tested. Ensure the scope aligns with your objectives.

Environment: Consider whether to perform the test in a production or staging/testing environment. You should also ask if it should be performed during normal business hours.

2. Legal and ethical boundaries

Legal and ethical boundaries are the foundational components of any successful penetration test.

■ Obtain necessary permissions and document all agreements.

■ Assign a compliance officer to ensure your organization aligns with relevant laws and regulations, such as data protection acts.

■ Ethical hackers must adhere to a code of conduct, respecting data privacy and integrity. For example, professional liability insurance might be necessary to cover any accidental damages or legal issues.

■ Stay informed about the changing legal landscape related to cybersecurity, hacking, and data protection.

■ Be aware of the legal implications of cross-border data transfers or accessing systems located in other jurisdictions.

■ Draft confidentiality or non-disclosure agreements to protect sensitive information.

3. Reconnaissance and Discovery

This phase involves gathering preliminary data, like network mapping and port scanning, to identify potential vulnerabilities and identify where to focus the testing efforts. There are two parts:

Passive: Collecting publicly available information without interacting directly with the target systems.

Active: Directly interacting with the network to gather detailed data like network mapping and port scanning.

4. Conducting the Penetration Test

The actual testing phase uses a blend of automated tools and manual techniques to simulate cyberattacks under controlled conditions and exploit identified vulnerabilities. The goal is to uncover security weaknesses without causing harm or disruption to the network.

1. Use automated scanning tools to scan the target systems for known vulnerabilities.

2. Once access is gained, establish a way to maintain access to the system for further exploration and analysis.

3. Test the possibility of extracting sensitive data from the target environment (this should be done with extreme caution and always within the legal and ethical boundaries).

5. Post-Test Actions, Analysis, Reporting, and Remediation

A penetration test isn't done until you finish the paperwork. In the post-test actions and remediation phase of network penetration testing, the focus is on addressing the vulnerabilities discovered during the test. The analysis can include:

Executive Summary

■ A high-level overview tailored for non-technical stakeholders.

■ Summarize the objectives, scope, and key findings of the penetration test.

■ Highlight critical vulnerabilities and potential business impacts.

Methodology and Scope

■ Detail the testing methodology used, including the types of tests (black box, white box, grey box).

■ Clarify the scope of the test, specifying which systems, networks, and applications were included.

Findings and Vulnerabilities

■ List each vulnerability discovered during the test.

■ Include a detailed description of how each vulnerability was discovered and exploited.

■ Provide evidence of the vulnerability, such as screenshots, logs, or code snippets.

Risk Assessment

■ Assess the risk level of each vulnerability, considering the likelihood of exploitation and potential impact.

■ Use a standardized risk rating system (like CVSS scores) for consistency.

Impact Analysis

■ Discuss the potential business and technical impacts of each vulnerability if exploited.

■ Include considerations like data loss, service disruption, compliance implications, and reputational damage.

Recommendations

■ Provide specific, actionable recommendations for remediating each identified vulnerability.

■ Suggest best practices for securing the systems against similar vulnerabilities in the future.

Timeline of Events

■ Outline the timeline of the penetration test, including when vulnerabilities were discovered and exploited.

Test Limitations

■ Discuss any limitations or constraints encountered during the test that might have affected the findings.

■ Mention any areas not covered in the scope that may require attention.

Understanding and implementing network penetration tests are crucial for testing your security posture, preventing data breaches, and ensuring network security.

Dotan Nahum is Head of Developer-First Security at Check Point Software Technologies
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