Constitutions of plant medicine emerge differently in cross-cultural encounters around healing, enlivened, stilled, and reconfigured in ways that deploy different medicinal profiles and approaches to conservation. This chapter presents the narratives of several Bribri, Afro Caribbean, and Tican healers in Talamanca, Costa Rica, as they reflect on medicinal encounters with seekers from North America, to elucidate the ways notions of people and plant relationships interpolate encounters and often participate in a broader colonial narrative by upholding a nature and society dualism. Ethnographic research in Talamanca is juxtaposed to discussions on plant medicine use in health contexts in British Columbia, Canada, providing a backdrop for considering emplacement in biotic context as elemental to plant becoming medicine. Emergent medicinal meanings and their relationship to broader economic, political, environmental, and social processes nuance some of the ways socioecological contexts are affected by the trajectories of seekers, and the consequences of a plant-centric and standardized perspective of plant medicine.