This study analyzed the influence of perceived time pressure, role clarity, working conditions and peer social support on the personal well-being (subjective, psychological and social well-being) of higher education students, in a sample of 128 Portuguese students from the University of Lisbon. A model was proposed which predicts a negative influence of time pressure and a positive influence of role clarity, working conditions and peer social support on students’ personal well-being, throughout the academic year. Data was collected by means of a longitudinal design, at the beginning and end of the academic year, through self-report questionnaires. Structural equation models were used to analyze cross-sectional and cross-lagged relations among the variables. At cross-sectional level, results revealed a good fit to data (CFI = .928; IFI = .931; RMSEA = .060) illustrating that the perception of academic context variables was related to well-being dimensions. At longitudinal level, however, cross-lagged models did not fit so well to the data (CFI = .863; IFI = .869; RMSEA = .058) with both perceptions of time pressure (β = .167; p = .037) and role clarity (β = –.288; p = .031) significantly predicting well-being, but not in the expected direction, encouraging the accomplishment of studies to further a broader understanding of higher education students’ well-being and its predictors. Implications for higher education scholars and practitioners and suggestions for future research are discussed.