Agricultural systems in the Upper Midwest region of the US are highly productive by some measures. Yet at the same time, these systems do not adequately sustain farmers, rural communities, or land and water resources. This challenge has contributed to calls for transformations to enhance sustainability and reduce the vulnerability of conventional agrifood systems. A socio-technical transformation of this size and complexity will require a collective effort among a network of actors. In other contexts, collaborative processes to encourage collective action among diverse network actors have been stymied by lock-in mechanisms (e.g., institutional, material, and cognitive). Here we examine network actors’ perceptions of the current barriers and problems facing the agrifood system of the Upper Midwest and opportunities for change and solutions for creative destabilization to overcome lock-in. Using interviews with network actors and the Constant Comparative Method, we identified salient barriers, including shared concern over limited resources to facilitate change and differences in actors’ vision for change. Yet many participants appeared to agree on solutions to destabilize prevailing industry resistance to change, including shifting power to farmers, providing resources for farmers to leverage their discursive legitimacy, and challenging cognitive sources of lock-in.