Objective: To examine trends in self-reported psychological distress among Canadian postsecondary students between 2020 and 2023. Participants and Methods: Using data collected from postsecondary students (n = 103,936) through the Canadian Campus Wellbeing Survey (CCWS), multilevel regression models were fitted to determine how distress levels, as measured by the Kessler Psychological Distress Scale, differed across six-time points of the CCWS. Results: Across the cycles, students reported high levels of distress (mean across cycles = 26.16, SD = 8.61). Considering the impact of time on distress, when compared to pre-COVID-19 pandemic, Fall 2020 (β = 1.4, p < .001), Spring 2021 (β = 1.2, p < .001), Spring 2022 (β = 1.6, p < .001), and Spring 2023 (β = 0.80, p < .017) had significantly higher levels of distress. Distress levels were associated with ancestry, age, gender, and sexual orientation. Conclusion: It is imperative to develop strategies and allocate resources to address the high levels of psychological distress among Canadian postsecondary students.