What challenge might Jim face if he conducts a gray box penetration test from offsite with provided RFC 1918 addresses?

The challenge Jim may face in conducting a gray box penetration test from offsite with provided RFC 1918 addresses is that these addresses are private and not routable on the public internet. RFC 1918 defines three ranges of IP addresses that are reserved for use in private networks: 10.0.0.0/8, 172.16.0.0/12, and 192.168.0.0/16. Because these addresses are meant to be used internally within organizations, conducting a penetration test from an external location, like offsite, means that Jim will be unable to reach and interact with the systems using those private IP addresses without a direct network connection or proper tunneling.

In the context of a gray box test, where Jim has some information about the target environment, the use of private IP addresses complicates the testing process when conducted remotely. This situation requires alternative methods, such as a Virtual Private Network (VPN) setup to access the internal network, which could introduce additional complexities or limitations.