The simplification of crop fields, farms, and agricultural landscapes is associated with decreased biodiversity and ecosystem services, such as natural pest control provided by arthropod natural enemies. While diversification may improve conservation and pest control outcomes in some cases, ecological predictions are often weak and habitat management at large spatial scales remains an unpopular strategy for agriculture. This dissertation seeks to address these agroecological challenges through multidisciplinary research that investigates the relationships among insects, crops, landscapes, and people in southern Wisconsin, USA, with a particular focus on predatory lady beetles (Coccinellidae). In the first chapter, I empirically test the prediction that landscapes with more abundant, stable prey resources support larger predator populations with a landscape-scale mensurative experiment in two study years. My results confirm the close association of lady beetles with semi-natural habitat, but do not provide evidence that adult lady beetle population sizes are influenced by spatio-temporal continuity of aphids in the landscape. A possible explanation for why I did not observe this hypothesized relationship is that aphids alone do not adequately capture the full diversity of resources utilized by lady beetles in heterogenous landscapes. Landscape supplementation—the process by which consumers benefit from substitutable resources from multiple adjacent habitats—could be an important mechanism for lady beetle persistence, but empirical evidence is lacking. My second chapter thus employs a DNA metabarcoding approach to investigate how the presence and taxonomic richness of arthropod prey in lady beetle diets vary by local habitat and landscape structure. Lady beetles communities in more diverse, cropped landscapes were associated with greater prey detection rates and prey taxa richness. Our results suggest that the realized diet breadth of wild lady beetles may be under-appreciated, and increasing the diversity of crop and non-crop habitats in a landscape may be an especially effective conservation strategy for mobile generalists. This work demonstrates that landscape-scale processes are consequential for natural enemies and biological control, but farmers do not typically have the ability to shape or decide their landscape context. Accordingly, my third chapter investigates the potential for temporally diversifying crops at the field-scale to enhance pest suppression. In a three year experiment, I compared aphids and predators in monocultures of early-season small grain crops and late-season soybeans to polycultures that contained temporally complementary crops in the same plot. I find that larger predator communities earlier in the growing season were associated with lower aphid population growth rates in soybean, but the impact of diversification on these dynamics was inconsistent, possibly because treatment differences were obscured by larger-scale processes. The substantial influence of landscape structure on conservation biocontrol outcomes underscores the importance of social processes in shaping agro-environmental outcomes. It is these processes to which I turn my attention in the fourth chapter, which draws from rural sociology, political ecology, and science and technology studies to analyze institutional constraints on the adoption ecological insect and landscape management practices by Wisconsin farmers. Overall, this dissertation illuminates pathways for the ecological intensification of agriculture and the adoption of alternative insect management paradigms. It identifies landscape-scale processes as integral components of more sustainable farming, making pest control and biodiversity conservation collective problems that require coordination among multiple stakeholders. To slow agricultural drivers of insect declines, large-scale coordination and political-economic change may be necessary. My findings contribute to the understanding of the socio-ecological complexities of insect natural enemy conservation in agricultural landscapes, and provide insights for the continued development of ecological intensification schemes.