Agri-environment schemes (AESs), ecological focus areas (EFAs), and organic farming are the main tools of the common agricultural policy (CAP) to counteract the dramatic decline of farmland biodiversity in Europe. However, their effectiveness is repeatedly doubted because it seems to vary when measured at the field-versus-landscape level and to depend on the regional environmental and land-use context. Understanding the heterogeneity of their effectiveness is thus crucial to developing management recommendations that maximize their efficacy. Using ensemble species distribution models and spatially explicit field-level information on crops grown, farming practice (organic/conventional), and applied AES/EFA from the Integrated Administration and Control System, we investigated the contributions of five groups of measures (buffer areas, cover crops, extensive grassland management, fallow land, and organic farming) to habitat suitability for 15 farmland bird species in the Mulde River Basin, Germany. We used a multiscale approach to identify the scale of effect of the selected measures. Using simulated land-use scenarios, we further examined how breeding habitat suitability would change if the measures were completely removed and if their adoption by farmers increased to meet conservation-informed targets. Buffer areas, fallow land, and extensive grassland were beneficial measures for most species, but cover crops and organic farming had contrasting effects across species. While different measures acted at different spatial scales, our results highlight the importance of land-use management at the landscape level—at which most measures had the strongest effect. We found that the current level of adoption of the measures delivers only modest gains in breeding habitat suitability. However, habitat suitability improved for the majority of species when the implementation of the measures was increased, suggesting that they could be effective conservation tools if higher adoption levels were reached. The heterogeneity of responses across species and spatial scales indicated that a mix of different measures, applied widely across the agricultural landscape, would likely maximize the benefits for biodiversity. This can only be achieved if the measures in the future CAP will be cooperatively designed in a regionally targeted way to improve their attractiveness for farmers and widen their uptake.