Many believe the current Canadian Dairy supply management system is outdated. Examining a recent consumer survey suggests consumers, especially among the younger generations, have mixed feelings about how the Canadian dairy industry is good for the environment or whether animals in the sector are humanely treated. The general Canadian public strongly supports financial stability for farmers, though is not fully educated about how supply management works. Issues regarding the centralization and amalgamation of the industry, making many regions underserved; recent milk dumping due to a strong shift in demand caused by COVID-19; and the popularity of dairy alternatives, show that the dairy sector in Canada is ill-prepared for major change. Dairy farmers are receiving compensation for trade deals recently ratified by the federal government, creating a precedent that will lead to an overcapitalized industry. The aim of this paper is to review the industry’s current state and suggest a roadmap for a more prosperous future.