This research examines the policy content of the Regional Official Plans in order to provide insight whether the regions of York and Peel are moving towards achieving sustainability. The study’s exploratory qualitative and comparative analysis examines the Regions’ contributions using the planning policies outlined in the recently released Regional Official Plans. Findings suggest that the Regions have emphasized sustainability-focused policies and have laid a foundation in achieving environmental and economic elements of sustainability. The analysis shows a low occurrence of policies that integrate social equity and justice issues with the economic and environmental objectives, which reduces the prospect of achieving sustainability. The comparative analysis suggests a number of directives that further can decrease the move towards achieving sustainability, including voluntary policies and indicators that may mislead a community in its progress towards sustainability. The study found that the Region of Peel has a higher presence of factors that can weaken the chances of achieving sustainability.