Rewardless orchid species are pollinated by deception and have reduced reproductive success. Those species that present self‐compatibility followed by alternative mechanisms of autogamy may compensate for such episodic allogamy events. This is the case for rain‐assisted self‐pollination, a rare mechanism in Orchidaceae. In this study, we investigated the reproductive biology of two terrestrial species: Cyrtopodium hatschbachii and C. paludicolum. We studied their reproductive systems, examined pollinators and male and female successes, and ascertained if rain promotes self‐pollination. Both species are allogamous but self‐compatible. However, natural fruit set is low, not exceeding 1.40% during 4 years of observation. This may result from the reduced frequency of pollinator visitation followed by a high pollinator specificity, because each species was pollinated by a single specialist bee. Although spontaneous selfing did not occur, we verified fruits formed by rain action. The evaporation of the water droplet that accumulates on stigma helps the pollinarium to slip back, promoting selfing. This occurred in approximately 10% of C. hatschbachii fruits, but in C. paludicolum it was recorded only once during three observation years. This indicates that the phenomenon happens at random and may vary temporally. Nevertheless, rain may confer additional fruit set, especially under circumstances of pollinator limitation. Overall, we confirmed deception as a strategy for this understudied genus. In addition, we report a further two cases of rain‐assisted self‐pollination for Cyrtopodium, for species from the center of diversity of the genus, indicating that it may be more widespread than previously thought.