A number of challenges affect the conservation of rare native species, including habitat availability and quality, the number and genetic diversity of existing populations, and the ease at reintroduction and augmentation of populations. Three threatened or endangered species in Oregon, Kincaid’s lupine (Lupinus sulphureus Douglas ex Hook. ssp. kincaidii (C.P. Sm.) L. Phillips [Fabaceae]), Willamette daisy (Erigeron decumbens Nutt. var. decumbens [Asteraceae]), and pink sand verbena (Abronia umbellata Lam. ssp. breviflora (Standl.) Munz [Nyctaginaceae]) provide examples of how, when considering these challenges, conservation prospects for a species can fall on a continuum from good to ugly. Lessons learned from working with these species may provide valuable tools that can be used to guide future conservation efforts.