For tremendous labor saving of land-use type agriculture, development research on remote monitoring-type uncrewed autonomous traveling systems, which enable uncrewed work in multiple fields, including movement between them, was conducted. In this system, position estimation for inter-field movement, detection of obstacles around the vehicle, and detection and recognition technology of operable farm road areas were developed as robotic implementations. An application for condition monitoring and operation of multiple robots was designed through a mobile terminal. In addition, a farm in virtual space was constructed based on a drone's survey data of the robot operation area, and a tool simulating robot movement was developed. This paper outlines the technology constituting the system and the technical problems to be solved, as well as the social issues for a practical operation of the system. In particular, given the characteristics of this system, in which an uncrewed robotic agricultural machinery autonomously travels on a road after finishing work in a field, comprehensive consultation, such as examination of the system design and social acceptability to enable the uncrewed operation, is required based on a system-operation situation under the current legal system.