Delayed selfing is a reproductive strategy that can increase mating opportunities and provide reproductive assurance in the absence of pollinators. When external pollination fails to occur in the herbaceous perennial, Kosteletzkya virginica, the styles curve downward to bring anthers into contact with the stigmal lobes, resulting in delayed selfing. Our goal was to evaluate experimentally the effects of weather conditions on pollinator activity, style curvature, and plant fitness. We discovered that adverse weather conditions significantly reduced pollinator visitation rates, and increased the incidence of style curvature, which resulted in delayed selfing. Furthermore, elimination of delayed selfing by experimental manipulation reduced fruit and seed set compared to non-emasculated flowers, even under adverse weather conditions. Offspring produced through selfing were similar to outcrossed progeny in the majority of fitness traits measured, and inbreeding depression was limited. Our study demonstrates that context-dependent style curvature promotes delayed selfing and provides reproductive assurance in the absence of pollinators, with minimal loss of progeny performance through inbreeding depression.