To increase donations of nutritious food, Ontario introduced a tax credit for farmers who donate agricultural products to food banks in 2013. This research seeks to investigate the role of Ontario's Food Donation Tax Credit for Farmers in addressing both food loss and waste (FLW) and food insecurity through a case study of fresh produce rescue in Windsor-Essex, Ontario. This research also documents the challenges associated with rescuing fresh produce from farms, as well as alternatives to donating. Interviews with food banks, producers and key informants revealed that perceptions of the tax credit, and the credit's ability to address FLW and food insecurity, contrasted greatly with the initial perceptions of the policymakers who created the tax credit. In particular, the legislators did not anticipate the logistical challenges associated with incentivizing this type of donation, nor the limitations of a donation-based intervention to provide food insecure Ontarians with access to fresh, nutritious food.