The Black-Box Approach for Penetration Testing

C.

The BEST methodology for the red team to follow, based on the scenario provided, is C. Examine the application using a port scanner, then run a vulnerability scanner against open ports looking for known, exploitable weaknesses the application and related services may have.

Explanation:

A black-box approach in penetration testing means that the red team has no prior knowledge of the system they are testing. They must act as an external attacker with no privileged access to the network. The goal of the test is to identify vulnerabilities that could be exploited by a real attacker. The black-box approach focuses on the external attack surface, which includes any entry point that an attacker could use to gain access to the system.

Option A, running a protocol analyzer to determine what traffic is flowing in and out of the server, and looking for ways to alter the data stream that will result in information leakage or a system failure, is not the best methodology for a black-box approach. This is because it assumes prior knowledge of the system, which is not allowed in a black-box approach.

Option B, sending out spear-phishing emails against users who are known to have access to the network-based application, so the red team can go on-site with valid credentials and use the software, is not the best methodology for a black-box approach. This is because it assumes prior knowledge of user credentials and access levels, which is not allowed in a black-box approach.

Option D, asking for more details regarding the engagement using social engineering tactics in an attempt to get the organization to disclose more information about the network application to make attacks easier, is not the best methodology for a black-box approach. This is because it relies on social engineering tactics that are not necessarily related to the technical vulnerabilities of the system.

Option C, examining the application using a port scanner, then running a vulnerability scanner against open ports looking for known, exploitable weaknesses the application and related services may have, is the best methodology for a black-box approach. This is because it is focused on identifying technical vulnerabilities in the system that an external attacker could exploit. A port scanner is a tool used to scan a range of IP addresses to determine which ones have open ports. Once open ports are identified, a vulnerability scanner is used to identify known vulnerabilities that could be exploited. This is a comprehensive approach that can identify a range of vulnerabilities in the system.

In conclusion, option C is the best methodology for the red team to follow in this scenario as it is focused on identifying technical vulnerabilities in the system that an external attacker could exploit, without any prior knowledge of the system.