Changes in landscape spatial structure—specifically, reductions in habitat area and connectivity—are thought to be a primary cause of pollinator declines across North America. However, the mechanisms by which landscape structure influences pollinator diversity are not well understood. Because flowering plants and pollinators are generally mutualistic, the impact of landscape structure on one can influence the diversity of the other directly or indirectly. Here, we examine the direct and indirect effects of landscape structure on plant and pollinator communities in the naturally patchy, dolomite glade grasslands of the Missouri Ozarks. We quantified landscape spatial structure and the richness of plants and flying invertebrate pollinators in 30 glades. Higher pollinator diversity was not directly related to greater landscape area and connectivity. However, we found evidence for an indirect relationship where better-connected landscapes support higher plant richness, which in turn supports greater pollinator diversity. Our findings highlight the importance of conserving extensive, well-connected natural habitat in order to maintain the plant diversity needed to support diverse pollinator communities.