Darjeeling’s famed tea plantations are staffed almost exclusively by an Indian Nepali (or Gorkha) labour force, whose ability to advance beyond field labour has been severely limited. In 2008, retired Gorkha plantation managers founded the Darjeeling Tea Management Training Centre (DTMTC). Though it was modeled on similar training programs, DTMTC’s goal had a twist: to prepare Gorkhas as plantation managers. According to DTMTC teachers, the contemporary Darjeeling tea industry remains precarious, stemming from a lack of knowledge on the part of Gorkhas as to how to run the industry. The DTMTC, then, was a novel blend of vocational training and political action. This chapter explores how the institute’s goals were interwoven with ideas of connection between people, plants and moral obligations to care for a Gorkha landscape—a landscape that might be improved with the right kinds of training.