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Abstract One of the current challenges for applied ecologists is to understand how to manage/restore agroecosystems in a sustainable and cost‐effective way. The intermediate landscape complexity hypothesis (ILCH) predicts that the effectiveness of agri‐environmental measures (AES) on biodiversity and ecosystem services recovery is often largest in landscapes of intermediate complexity. This hypothesis has rarely been tested in savanna‐like permanent agroecosystems. Focusing on pollinators, we test the ILCH at the regional scale in Mediterranean olive orchards, one of the most important permanent agroecosystems in the world. We inferred abundance of cavity‐nesting pollinators in 40 paired olive orchards (extensively vs. intensively managed herbaceous cover) in 20 localities selected across a landscape complexity gradient. We also studied how different magnitudes in local management switches may affect pollinators by considering organic and intensive fields as management extremes in olive orchards. We used 208 trap nests for solitary bees to measure colonization rates. Additionally, we conducted pollinator surveys to ascertain that colonization rate was a representative proxy for pollinator activity. Our results showed that (a) changes in colonization rates due to local herb cover management peaked at intermediate landscape complexity, with extensively managed fields rendering higher colonization rates. (b) Organic fields had higher colonization rates than their control farms regardless of landscape complexity. (c) There was a highly significant correlation between nest colonization rates and density of pollinators foraging on flowers, which suggests that colonization rate is a good estimator of pollinator activity. Policy implications . The maintenance of ground herb cover (main agri‐environmental measure in olive orchards) is a cost‐effective investment allowing recuperation of pollinators when targeting olive farms located in landscapes of intermediate complexity. Additionally, fostering organic farming (still minority in olive groves) for the conservation of solitary bees should be a priority for policymakers since its effects are beneficial in any landscape.