Previous research assessing correctional worker (CW) mental health has seldom assessed for differences based on jurisdiction or diverse occupational categories. The current study was designed to provide a nuanced quantitative examination of mental health disorder prevalence and related problems among CWs and to qualitatively explore the varying social contexts surrounding CW well-being. We reflect on how we overcame unanticipated challenges and disruptions (e.g., technology, COVID-19 pandemic) throughout the design, launch, and analysis of the survey, and illustrate how our national study, driven by a rigorous methodological approach and collaborative research design, builds on the extant CW mental health and wellness literature.