Wildfire-mediated changes to forests have prompted numerous studies on post-fire forest recovery of coniferous forests. Given climate change, a growing body of work demonstrates that conifer regeneration in temperate and boreal forests is declining, a phenomenon often termed 'regeneration failure.' However, the definition and parameters are numerous and variable. Characterization of drought also varies greatly, thus hindering the ability to compare results among areas. This review discusses new perspectives on conifer regeneration failure and places these studies into the context of drought and fire activity. We focus this review on three forest types where conifer regeneration failure is well documented: western boreal forests, cold mixed-conifer forests, and dry pine forests. To place the challenges to conifer tree regeneration in the context of regional climate trends, we present a novel regional analysis that summarizes drought conditions prior, during, and following the year of a large wildfire. We demonstrate the need to assess failure in the context of specific forest dynamics and well-defined metrics. For example, tree establishment may historically occur over longer periods, and current and future climate may exacerbate this and not promote pre-fire forest structure and composition. Many forests are undergoing rapid change and the type, magnitude, and causes of changes need to be compared among areas. As such, we should be cautious of quantifying “regeneration failure” and drought without providing spatial and temporal context.