The Mediterranean flora is spectacularly rich in orchid species that have evolved remarkable adaptations to their environment. Orchids have complex and delicate interactions with their pollinators, which makes them particularly prone to local extinction. Conservation actions should be encouraged for a range of endangered Mediterranean orchid species, but the current taxonomic confusion in several genera and the apparent disagreement among orchid taxonomists make the situation particularly confusing from a conservation perspective. In this review, we document how the different pollination syndromes of Mediterranean orchids (nectar reward, shelter offering, food deception and sexual deception) can have a profound impact on the type of reproductive barriers among species, on floral phenotypic variation as we perceive it, on potentially related processes of species sorting and extinction and, consequently, should have a strong influence on the related conservation management programs. We also highlight that the majority of Mediterranean orchids are pollinated by specialised bees often occupying otherwise narrow ecological niches (e.g. pollen specialisation, brood cell parasites, specific nesting site). This condition makes the orchid-pollinator interactions very fragile and several orchid species prone to local extinction. We illustrate this phenomenon by a selection of case studies that show how the adequate integration of the ecological requirements/traits of the orchids and their associated pollinators into conservation actions could help protect endangered species and ensure the sustainability of the often complex local pollination web.