This causal comparative study explored K-12 educators' and school staff's self-reported levels of well-being, perceived stress, and use of coping strategies. An online survey was administered to 686 educators consisting of teachers, school administrators, professional support staff, administrative support staff and other school staff in a medium-sized schoolboard in Southern Ontario, Canada. The results show that educators reported overall low scores of wellbeing and higher levels of perceived stress as compared to the general population. Female educators reported significantly higher perceived stress than their male colleagues. A "k-means" cluster analysis of the educators' coping strategies identified four unique clusters which were significantly different from each other. It was shown that participants in two of the clusters, consisting of approximately 32% of the participants in this study, used maladaptive coping strategies more frequent and that the participants in these two clusters exhibited significantly poorer wellbeing and significantly more perceived stress than their colleagues in the other two clusters. The limitations and practical implications of this study are discussed.