Smallholder farmers and indigenous communities must cope with the opportunities and threats presented by rapidly spreading estate crops in the frontier of the agricultural market economy. Smallholder communities are subject to considerable speculation by outsiders, yet large-scale agriculture presents tradeoffs that they must navigate. We initiated a study in Sintang, West Kalimantan in 2012 and have returned annually for the last four years, building the baselines for a longer-term landscape approach to reconciling conservation and development tradeoffs in situ. Here, the stakeholders are heterogeneous, yet the land cover of the landscape is on a trajectory towards homogenous mono-cropping systems, primarily either palm oil or rubber. In one village on the frontier of the agricultural market economy, natural forests remain managed by the indigenous and local community but economics further intrude on forest use decisions. Conservation values are declining and the future of the forest is uncertain. As such, the community is ultimately attracted to more economically attractive uses of the land for local development oil palm or rubber mono-crop farms. We identify poverty as a threat to community-managed conservation success in the face of economic pressures to convert forest to intensive agriculture. We provide evidence that lucrative alternatives will challenge community-managed forests when prosperity seems achievable. To alleviate this trend, we identify formalized traditional management and landscape governance solutions to nurture a more sustainable landscape transition.