In the last 200 yr, more than 80% of the land in the U.S. Corn Belt agro-ecosystem has been converted from natural perennial vegetation to intensive agricultural production of row crops. Despite research showing how re-integration of perennial vegetation, e.g., cover crops, pasture, riparian buffers, and restored wetlands, at strategic landscape positions can bolster declining regional ecosystem functions, the amount of land area devoted to row crop production in the Corn Belt continues to increase. As this region enters a time of fast-paced and uncertain reorganization driven by the emerging bioeconomy, changes in land use will continue to take place that will impact the resilience of the Corn Belt’s linked social and ecological systems for years to come. Both resilience theory and the diffusion of innovations theory investigate how change is brought about in systems through the adaptation and innovation of social actors. In this paper, we integrate these two frameworks in the analysis of 33 in-depth interviews to improve our understanding of how rural Corn Belt stakeholders make conservation decisions in the midst of an uncertain future. Interview data indicate that the adoption of conservation practices is based not only on immediate profitability but also on the interplay between contextual factors at three distinct levels of the system: compatibility with farm priorities, profitability, practices, and technologies; community-level reinforcement through local social networks, norms, and support structures; and consistent, straightforward, flexible, and well-targeted incentives and regulations issuing from regional institutions. Interviewees suggest that the multiscale drivers that currently support the continued expansion of row crop production could be realigned with conservation objectives in landscapes of the future. Adaptation of social actors through collaborative learning at the community level may be instrumental in brokering the sort of multiscale system change that would lead to more widespread adoption of perennial cover types in the Corn Belt.