ABSTRACT Specialized pollination systems frequently match a particular set of floral characteristics. Vincetoxicum spp. (Apocynaceae, Asclepiadoideae) have disk‐shaped flowers with open access to rewards and reproductive organs. Flowers with these traits are usually associated with generalized pollination. However, the highly modified androecium and gynoecium that characterize asclepiads are thought to be associated with specialized pollinators. In V. sangyojarniae, we investigated floral biology, pollination, and the degree of pollinator specialization in two localities in Thailand. We examined floral traits that target legitimate pollinators. Flowers of V. sangyojarniae opened only at night, emitted floral scents containing mainly (E)‐β‐ocimene, 1‐octen‐3‐ol, (E)‐4,8‐dimethyl‐1,3,7‐nonatriene (E‐DMNT) and N‐(3‐methylbutyl)acetamide, and provided sucrose‐dominated nectar openly to insect visitors. Assessment of pollinator effectiveness indicated that V. sangyojarniae is functionally specialized for pollination by cecidomyiid flies. Although various insects, particularly cockroaches, frequently visited flowers, they did not carry pollinaria. Our results suggest that V. sangyojarniae attracts its fly pollinators by emitting floral volatiles bearing olfactory notes associated with the presence of fungi or, less likely, of prey captured by predatory arthropods (food sources of its pollinators) but offers a nectar reward upon insect arrival. Hence, there is a mismatch between the advertisement and the actual reward. Our results also suggest that the size of floral parts constitutes a mechanical filter where reciprocal fit between flower and insect structures ensures that only suitable pollinators can extract the pollinaria, a prerequisite for successful pollination. Vincetoxicum sangyojarniae combines nectar reward with food deception to attract its pollinators and ensures successful pollination through reciprocal mechanical fit between plant reproductive organs and insect structures.