We evaluated farmers’ rationales to understand their decision making in relation to the use of fertile anthropogenic soils, i.e., Amazonian dark earths (ADE), and for dealing with changes in shifting cultivation in Central Amazonia. We analyzed qualitative information from 196 interviews with farmers in 21 riverine villages along the Madeira River. In order to decide about crop management options to attain their livelihood objectives, farmers rely on an integrated and dynamic understanding of their biophysical and social environment. Farmers associate fallow development with higher crop yields and lower weed pressure, but ADE is always associated with high yields and high weeding requirements. Amazonian dark earths are also seen as an opportunity to grow different crops and/or grow crops in more intensified management systems. However, farmers often maintain simultaneously intensive swiddens on ADE and extensive swiddens on nonanthropogenic soils. Farmers acknowledge numerous changes in their socioeconomic environment that affect their shifting cultivation systems, particularly their growing interaction with market economies and the incorporation of modern agricultural practices. Farmers considered that shifting cultivation systems on ADE tend to be more prone to changes leading to intensification, and we identified cases, e.g., swiddens used for watermelon cultivation, in which market demand led to overintensification and resulted in ADE degradation. This shows that increasing intensification can be a potential threat to ADE and can undermine the importance of these soils for agricultural production, for the conservation of agrobiodiversity, and for local livelihoods. Given that farmers have an integrated knowledge of their context and respond to socioeconomic and agro-ecological changes in their environment, we argue that understanding farmers’ knowledge and rationales is crucial to identify sustainable pathways for the future of ADE and of smallholder agriculture in Amazonia.