Published in the Natural Areas Journal: Rare species recovery presents several challenges for conservation managers, particularly when listed species interact with one another. We present a case study involving two such species: golden paintbrush (Castilleja levisecta) and Taylor’s checkerspot butterfly (Euphydryas editha taylori), both of which occur in lowland prairies in the Puget Sound region and are federally protected (threatened and endangered, respectively). These two species occupy some of the same sites, and golden paintbrush likely historically served as a larval food plant for Taylor’s checkerspot. Managers working to recover these species have encountered a number of challenges and opportunities—recovery efforts for one species may have no effect, positive effects, or negative effects on the other. Furthermore, sometimes rapid recovery actions are necessary on shorter time scales than those at which research typically occurs, and must proceed in spite of significant knowledge gaps. Here we share how our growing understanding of the complex ecology of these species has given rise to large-scale management questions and conflicts, and outline the strategies we are using to navigate these challenges. Our approach has included convening periodic workshops with experts on both species; designing and implementing research studies to fill knowledge gaps about the two species’ relationship; and identifying “no regrets” actions that can be taken to benefit one or both species with minimal risk in the face of uncertainty. While the details of this case study are highly specific, the lessons can be applied to other systems with interacting listed species.