In Europe, the surface devoted to sunflower cultivation has expanded by ∼ 26% from 2006 to 2016. Theoretically, this implies an increasing demand for pollinators, while at the same time, scientific reports claim that pollinator communities worldwide are threatened by multiple stressors such as agrochemicals, the loss of suitable habitats and habitat fragmentation. However, the question that arises is whether insect pollination is still relevant for modern sunflower varieties that are often highly self-fertile. Following recent studies which demonstrate that surrounding land use composition may affect ecosystem service provisioning in cropped fields, this study aims at re-examining the pollination status of sunflower while disentangling the effects of local and landscape variables on sunflower seed set and oil content in Central Italy. Commercial cultivars, regardless of their degree of self-fertility, showed increased seed set and oil content when receiving adequate amounts of cross-pollination; oil composition, though, was not affected by cross-pollination events. Honey bees accounted for the vast majority of pollinators ensuring an overall adequate pollination. Sunflower seed set was higher in fields surrounded by landscapes containing a greater abundance of beehives, early flowering crops, urban areas and woody linear elements; conversely, seed set was lower where herbaceous semi-natural habitats dominated the surrounding landscape. This information is necessary for a science-based planning of agricultural policies and shows that, despite the adoption of self-fertile cultivars, sunflower still benefits from insect pollination and land use planning may affect crop productivity.