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(1) Objective: To longitudinally assess food and beverages sold in vending machines in secondary schools (grades 9-12) participating in the COMPASS study (2015/2016 and 2018/2019) and (2) to examine if patterns and trends observed in previous years (2012/2013 to 2014/2015) are consistent with lack of policy compliance in Ontario and Alberta, Canada. (2) Methods: Policy compliance was assessed through comparing nutritional information on drink (e.g., sports drinks) and snack (e.g., chocolate bars) products in vending machines to Policy and Program Memorandum (P/PM) 150 in Ontario (required policy) and the Alberta Nutrition Guidelines for Children and Youth (recommended policy). Longitudinal results and descriptive statistics were calculated. (3) Results: Longitudinal results indicate that between Y 4 (2015/2016) and Y 7 (2018/2019), snack and drink vending machines remained mostly non-compliant in Ontario and Alberta, with a small proportion of Ontario drink machines changing from non-compliant to compliant. At the school level, descriptive results indicate the proportion of Ontario schools with policy-compliant snack and drink machines decreased between Y 4 and Y 7 . Alberta schools were non-compliant for drink and snack machines. (4) Conclusions: Secondary schools continue to be non-compliant with provincial policies. School nutrition policies need to be simplified in order to make it easier for schools to be compliant. Enforcement of compliancy is also an area that deserves consideration.