This paper employs mean-variance and mean-skewness optimization to investigate farmers’ crop choices under Gross Revenue Insurance (GRIP), Whole Farm Income Insurance, the Canadian Agricultural Income Stabilization program, and its modified 2008 program AgrInvest. To our knowledge this paper is the first to fully consider the endogenous optimization of whole farm insurance in a farm optimization model. The results indicate that farmers will alter farm plans significantly in response to the type of insurance offered and the level of subsidy. Farmers will take on production risks that they would not otherwise take and this risk taking behavior is exacerbated by subsidy.