Delayed HIV diagnosis among men who have sex with men (MSM) in the United States continues to be a significant personal and public health issue. Using qualitative and quantitative data from 75 recently tested, HIV-sero-positive MSM (38 delayed and 37 nondelayed testers), the authors sought to further elucidate potential personal and contextual factors that may contribute to delayed HIV diagnosis among MSM. Findings indicate that MSM who experience multiple life stressors, whether personal or contextual, have an increased likelihood of delaying HIV diagnosis. Furthermore, MSM who experience multiple life stressors without the scaffolding of social support, stable mental health, and self-efficacy to engage in protective health behaviors may be particularly vulnerable to delaying diagnosis. Interventions targeting these factors as well as structural interventions targeting physiological and safety concerns are needed to help MSM handle their life stressors more effectively and seek HIV testing in a timelier manner.