Our study was undertaken to better understand how to increase the success rates of recovery plantings of a rare hemiparasite, golden paintbrush (Castilleja levisecta—Orobanchaceae). This species is endemic to western Washington and Oregon, USA, and southwestern British Columbia, Canada. Over 5000 golden paintbrush plants were outplanted as plugs in 2007 at six different native prairie sites that were considered to be suitable habitat, based on general evaluations of vegetation and soil conditions. Outplantings were installed at regular intervals along transects up to 1 km long to include a range of conditions occurring at each site. All plantings were re-examined five years later. The patchy distribution of surviving plugs and new recruits within each reintroduction site suggested success is strongly influenced by microsite characteristics. Indicator species analysis of taxa growing in microsites around outplanted golden paintbrush identified species that were positively or negatively associated with paintbrush survival. Species such as Festuca roemeri, Eriophyllum lanatum, and Viola adunca were strong indicators at some sites; non-natives such as Hypochaeris radicata and Teesdalia nudicaulis tended to be frequent negative indicators. Overall, higher richness of native perennial forbs was strongly correlated with both survival and flowering of golden paintbrush, a pattern that may reflect interactions of this hemiparasite with the immediately surrounding plant community. Topographic position also influenced outcomes, with greater survival occurring on mounds and in swales, where soils generally were deeper. Our findings suggest that assessments of site suitability based on vegetation alone, and coarser, site-level assessments that do not characterize heterogeneity at the microsite scale, may not be strong predictors of restoration success over the longer term and in sites with variability in vegetation and soils. By identifying suitable microsites to focus rare species plantings, survival and efficiency may be significantly enhanced.