<p>Bicultural stress, or challenges from navigating two cultural contexts, is common among youth from immigrant backgrounds. Despite advances in developmental and cultural stress theories that situate bicultural stress in the social contexts of youth’s everyday lives, much of the extant research relies on cross-sectional designs that are not able to examine how bicultural stress may change over time across sociocultural transitions. This study examined U.S. Latino adolescents’ daily diary-reported bicultural stress on two occasions as they transitioned from high school to college, as well as theoretically informed sociocultural correlates of daily bicultural stress both cross-sectionally and longitudinally. Participants were recruited through a university partnership and eligible for this study if they were Latino adolescents in the final year of high school, lived within a large metropolitan area in the U.S. Southwest, and had gained acceptance to the university the following year (<i>N</i> = 206; <i>M</i>_age = 18.10 years, <i>SD</i> = 0.41; 65.4% female identifying; 84.9% Mexican origin; 68.8% first-generation college). Daily diaries were collected across seven days on two occasions – before and after college transition. Results from latent difference score modeling indicated that daily bicultural stress levels and day-to-day stress variability decreased from high school to college, on average. Longitudinal changes in daily bicultural stress varied across social position and context factors (e.g., gender, immigrant generation, first-generation college status). This highlights variability in the extent to which daily bicultural stress changes over time as Latino adolescents navigate a prominent sociocultural transition. The results contribute to better understanding adolescent stress processes from a cultural perspective and offer practitioners and policymakers insights into the diversity of experiences among youth who navigate bicultural stress.</p>