Changes to agri-environmental policy, with an emphasis on encouraging more environmentally friendly farming practices, have been paralleled in the last two decades by a body of research into agri-environment scheme adoption. To date much of this research has considered conservation behaviour as a static issue across whole farms, and viewed participation decisions as solely a present-day issue. Based on an in-depth case study from the Peak District (UK) this paper considers the case of hay meadows—an important cultural, ecological and agricultural feature of the landscape which has been seriously threatened by changing farm practices during the last century, and which now features as a conservation option in the main agri-environment schemes. Drawing on material from semi-structured interviews on 62 farms, and participant observation on 20 farms, the paper discusses how hay meadows represent a unique case for conservation and considers the limitations of existing conceptualisations of scheme adoption for understanding hay meadow conservation. In particular, the paper examines how current conservation decisions are constrained by, and intersect with, past managements that affect the “eligibility” of meadows for scheme adoption. A model is developed which places meadow types of different eligibility against conservation styles to illustrate how different conservation scenarios are created.