We report on how a long-term study of the reproductive biology of the Critically Endangered Schiedea adamantis (Caryophyllaceae), one of Hawai‘i's rarest plant species, was leveraged for conservation purposes. Our major goals were to provide seeds with the greatest genetic variation possible for reintroduction and to ensure that both female and hermaphroditic plants of this wind-pollinated species were reintroduced in a manner that maximized both outcrossing and seed production. Schiedea adamantis was one of the first Hawaiian plant species listed under the Endangered Species Act (USA). The species has been studied intensively to test hypotheses addressing the evolution of breeding systems. Information on outcrossing levels and the extent of inbreeding depression was integrated into ongoing reintroduction efforts. Population size peaked in 1994, when 267 flowering individuals were found on Lē‘ahi (Diamond Head Crater). By 2016 only 17 flowering individuals were present, with drought and invasive species being possible causes of this decline. Reintroduction attempts in 1998 using genetically diverse seeds were unsuccessful because of drought and a lack of sufficient supplemental irrigation. Additional reintroduction attempts in 2012 and 2014 were more successful because of increased supplemental irrigation. Plants used in reintroductions represent genotypes long since absent in the natural population, and may contain the genetic variability essential for evolutionary responses to climate change and the spread of invasive species. The destruction of many plants reintroduced in 2015 and 2016 by a fire in March 2016 highlights the need for additional restoration areas at Lē‘ahi and elsewhere, and storage of seeds for future use.