Despite marked improvements, intervention for students with a mental health problem or illness in Canadian higher education settings remains not yet successful, mature, or sustainable. A number of challenges have been identified as contributory to the shortcomings surrounding student mental health in colleges and universities. In this paper, I explore some of the more common barriers that currently limit the development, implementation, and sustainability of student mental health support practices. The barriers of focus include, prevailing stigma and stereotypes, underdeveloped policies, and minimal opportunities for professional development and training. I specifically highlight how these barriers frame the challenges for teaching faculty and academic staff in promoting or supporting student mental health and well-being. Following an identification and discussion of barriers, I offer suggestions on how they can be overcome, or at the very least minimized, and what this would mean for teaching and learning in relation to post-secondary student mental health. For example, in an attempt to clarify current policies surrounding mental health, I suggest and explore how institutions can assign particular individuals (i.e., a designated "task force") as responsible for the development, implementation, and evaluation of mental health policies. Ultimately, the first step to better mental health support practices is to acknowledge how they are challenged.