||Although population declines of grassland songbirds in North America and Europe are well-documented, the effect of local processes on regional population persistence is unclear. To assess population viability of grassland songbirds at a regional scale (similar to 150,000ha), we quantified Savannah Sparrow Passerculus sandwichensis and Bobolink Dolichonyx oryzivorus annual productivity, adult apparent survival, habitat selection, and density in the four most (regionally) common grassland treatments. We applied these data to a female-based, stochastic, pre-breeding population model to examine whether current grassland management practices can sustain viable populations of breeding songbirds. Additionally, we evaluated six conservation strategies to determine which would most effectively increase population trends. Given baseline conditions, over 10 years, simulations showed a slightly declining or stable Savannah Sparrow population (mean bootstrap lambda = 0.99; 95% CI = 1.00-0.989) and severely declining Bobolink population (mean bootstrap lambda = 0.75; 95% CI = 0.753-0.747). Savannah Sparrow populations were sensitive to increases in all demographic parameters, particularly adult survival. However for Bobolinks, increasing adult apparent survival, juvenile apparent survival, or preference by changing habitat selection cues for late-hayed fields (highest quality) only slightly decreased the rate of decline. For both species, increasing the amount of high-quality habitat (late- and middle-hayed) marginally slowed population declines; increasing the amount of low-quality habitat (early-hayed and grazed) marginally increased population declines. Both species were most sensitive to low productivity and survival on early-hayed fields, despite the fact that this habitat comprised only 18% of the landscape. Management plans for all agricultural regions should increase quality on both low- and high-quality fields by balancing habitat needs, nesting phenology, and species’ response to management.