Abstract: A system may include a file transfer manager that determines a file for transfer from a source location to a target location, the file being associated with file metadata characterizing the file, and with an organization. The file transfer manager may include an orchestrator that determines at least two transfer paths for the transfer, including at least a first transfer path utilizing a private wide area network (WAN) of the organization and a second transfer path utilizing a publicly available data hosting service, access transfer metadata characterizing the at least two transfer paths, and access organizational metadata characterizing organizational transfer path usage factors. The file transfer manager also may include a heuristics engine configured to execute path decision logic using the file metadata, the transfer metadata, and the organizational metadata, to select a selected transfer path from the at least two transfer paths.