Despite considerable evidence that attachment theory is a valuable framework for understanding educational outcomes, associations between attachment representations, academic burnout, engagement, and drop-out have been largely overlooked. In this study, 290 first-year post-secondary students completed attachment, academic burnout, and academic engagement questionnaires; 15% of the 290 students did not return for their second year. Using Structural Equation Modelling, we were able to simultaneously test the associations among variables while controlling for measurement error which may attenuate or overestimate the associations between variables. We also tested whether the associations were similar when the decision to drop-out was added to the model. Attachment anxiety, but not attachment approach-avoidance, was found to be associated with higher burnout and lower engagement. Furthermore, higher burnout increased chances of drop-out. Implications of these findings for universities include consideration of attachment relationships when developing interventions to reduce student burnout, disengagement, and drop-out is discussed.