Final answer:
The most appropriate tool to use in this scenario would be a Reverse shell endpoint listener as it provides a means to bypass firewalls and NIDS for data exfiltration and commands upload during an authorized test.
Step-by-step explanation:
The student is asking which tool should be loaded onto a device designed for exfiltrating data during an authorized test while bypassing security measures. The most effective and relevant option would be D. Reverse shell endpoint listener. This tool would allow the security engineer to initiate a connection from the target network back to the command-and-control server, effectively bypassing firewalls and Network Intrusion Detection Systems (NIDS) which typically monitor inbound connections. Custom firmware with rotating key generation is relevant for encryption and authentication, but not specifically for bypassing network defenses. An automatic Man-In-The-Middle (MITM) proxy could be useful for manipulating traffic, but it is more relevant for intercepting communication rather than establishing a connection with a C2 server. TCP beacon broadcast software might help to signal a presence but does not set up a channel for command upload or data exfiltration effectively as required.