Although the shift to online learning has been gaining momentum, the current global pandemic has forced institutions to pivot to virtual learning environments. This pilot study evaluates the efficacy of three permutations of a multi-week wellness intervention on mental health, mindfulness, and loneliness in order to examine the effects of different online learning conditions during COVID-19. Undergraduate students were randomly assigned to one of three conditions manipulating the format through which the training was conducted: 1) asynchronous self-guided sessions, 2) synchronous online sessions with a live facilitator, and 3) a hybrid between asynchronous self-guided sessions and brief synchronous online sessions with a live facilitator. Results suggest that all conditions, despite their synchrony, show changes over time; however, counter to our expectations, participants show decreases in mindfulness, increases in loneliness, and non-significant changes to their mental health. To better understand this surprising finding, we analysed short answer responses to find that as stress increases, wellness training can be perceived as “just another task” that overwhelms rather than reduces experiences of wellbeing. This research underscores the importance of considering contextual factors, like a global pandemic or preferences to value achievement over wellbeing, when making decisions around when and how to implement wellness programs.