This investigation focuses on the decision making relative to plants by Native Americans on one of the oldest and most continuously occupied reservations in the United States, the Mashantucket Pequot Nation. Within an agency framework, I explore the directions in which decision making about plants were changing from 1675-1800 A.D. I evaluate plant macroremains, specifically progagules (seeds), recovered from ten archaeological sites and the historical record from the Mashantucket Pequot Reservation, located in southeastern Connecticut. I demonstrate how decision making about plants related to food and medicinal practices during the Colonial Period were characterized by heterarchical choices that allowed the Mashantucket Pequot to retain their sense of economic and cultural autonomy from their colonizers. This type of problem-directed agency analysis will aid in placing Indigenous individuals and communities into the contexts of colonization as more active participants in their own past, and as long-term stewards of the environment. More specifically, this dissertation shows that even as small a space as the Mashantucket Pequot Reservation is a rich testimony to the 11,000-year history, and continues to provide important information about how households and communities (re)conceptualize their socio-natural worlds under the most severe constraints.