Ensuring comfort for an AR/VR/XR head and face worn product is a time consuming challenge when relying on user comfort testing only. This study researches the relationship between pressure levels in the forehead region and subjective comfort ratings during long-term wear. By applying known loads to the forehead and coupling detailed load, material characterization, and empirical device fit with structural Finite Element Analysis (FEA) models, the forehead pressure distribution could be calculated per user. When these pressure distributions are mapped to comfort experiences of users, identification of pressure comfort thresholds for the forehead becomes possible. Participants wore a custom headset that could apply a set, known force to the forehead, for 4 h. Two force loads, 3.5 N and 8 N, were evaluated. Several pressure metrics such as average, peak, areas, and gradients were included in the assessment. Clear distinction between forehead comfort pass and fail was identified for average pressure and pressure gradient between 60–65th percentile values.