Derailment, or the sense that one has gotten “off-course” in terms of who they are and where they are going, has been nominated as a precursor to psychological ills like depressive symptoms. However, what the development of these depressive symptoms implies for continued feelings of derailment remains in question. The present study investigated a potential feedback loop between depression and derailment to explain how these two phenomena may persist through time. College students (N = 939, 63.6% female) were asked to take part in a preregistered, 4-wave longitudinal study over the course of one academic year. An autoregressive latent trajectory model with structured residuals was developed to test the bidirectional associations of these variables at the within-person level, asking whether deviations from one’s mean trajectory on depression can predict downstream deviations from one’s mean trajectory on derailment and vice-versa. Depression and derailment evidenced significant autoregressive stability from one wave to the next, and significant positive covariation within most waves. Depression was found to significantly and positively predict later derailment across all cross-lagged components of the model, thus supporting the hypotheses of the present study. Derailment was found to significantly and negatively predict depression in two of the three cross-lagged components, thus failing to support the hypotheses of the present study. Given some of these unexpected findings, results are discussed with an eye toward future work uncovering potential moderators of the association between derailment and resultant depressive symptoms.