Cost efficiency and productivity as well as drivers comfort and usability are significant innovation drivers for agricultural machinery. The proposed electronic tow bar system for tillage processes consists of two vehicles, coupled by wireless data connection. An unmanned slave tractor follows a master tractor with a position dependent lateral and longitudinal offset. Operating two tractors with one driver only, increases productivity and improves the capacity load due to higher flexibility in fleet management. In return, the usability and safety of the tow bar becomes a major concern, which is addressed by an elaborate safety concept enabled by sensor based obstacle detection and mapping. Web-based geo-information, are used to support proactive path planning.This paper presents a solution to achieve both, safety and usability, for a complex platoon system. The interaction of the operator with the local and global obstacle map is designed to meet the requirements of both target functions.