This case study describes our experiences in conducting a correlational study in which we examined the unique associations between the five pathological personality traits assessed in the alternative model of personality disorders introduced in the 5th edition of the Diagnostic and Statistical Manual of Mental Disorders (DSM-5) and thoughts that perpetuate criminal behavior (i.e., criminogenic thinking). The study was designed to take place within state prisons operated by the Mississippi Department of Corrections and utilize a sample of incarcerated adult male offenders. Once data collection was underway, we decided to expand the scope of the study by adding a community sample from which data were collected online using Amazon's Mechanical Turk. This expansion permitted us to compare the relationships between pathological personality traits and criminogenic thinking in community adults and incarcerated offenders. This case study describes the rationale and context for our research, discusses several of the challenges we faced, explains our methodological choices, and highlights some of the lessons we learned.