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Grassland bird conservation is a complex and nuanced issue, and the solutions are not always obvious or simple. Hyla Howe, Grassland Bird Biologist at Mass Audubon and coordinator for the Bobolink Project, will explain what the team has learned from the program’s first decade, the challenges that have surfaced, the opportunities that persist, and the changes that are underway to expand and improve the program. After almost a decade of slow but steady growth, the program has received federal funding to greatly expand the acreage enrolled in Vermont’s Champlain and Connecticut River Valleys, which brings immense opportunity but also raises critical questions.  How can we integrate grassland bird-friendly haying timelines with the needs of working farms? How do we maintain fields that have gone out of production so they can continue to support grassland species? How can we scale our model and offer more support to farmers by working with local volunteers? In a time when the future is uncertain for grassland-obligate species, it is necessary to listen deeply to the people who are managing these vital landscapes and implement solutions that protect the resilience of our agricultural lands.