Pollinators are needed for the reproduction of Echites umbellatus, and only sphingid moths have mouthparts long enough to reach the nectar at the bottom of the species’ long, twisted floral tube. Though plants produce many flowers over a period of several months, one observes very few fruits in nature. We asked: (1) Are plants self-compatible, or do they need pollen from another individual to set fruit and seed? (2) Are cross-pollinations between unrelated individuals more successful than crosses with relatives? (3) How does the relatedness of pollen and ovule parent plants affect fruit set, seed number, and seed quality? We investigated the breeding system of E. umbellatus by collecting fruits from seven sites, growing plants and performing hand pollinations over a period of several years, collecting and measuring fruits and counting seeds. Echites umbellatus is self-incompatible, though some individuals produce fruit by self-pollination. Cross-pollinations between unrelated individuals set the most fruit (59%), and those that were self-pollinated set the least (9%). Fruit set from cross-pollinations between related individuals was intermediate (32%). Although the number of seeds per fruit did not differ significantly among pollination treatments, fruits from self-pollinations had substantially fewer viable seeds than outcrossed fruits, with fruits from sibling crosses being intermediate. There were higher levels of self-compatibility in the fragment populations compared with plants from intact habitats. Self-incompatibility may explain why fruit set is low in this plant species; future investigation into the breakdown of self-incompatibility in smaller populations is warranted.