This study examines the use of advance selling in the wine industry as a form of operational flexibility to mitigate quality rating risk. The process of making fine wine begins after the harvesting season. During this time, grapes are sorted, pressed into juice, and are left to be fermented in barrels for up to 2 years. After 6 to 8 months of barrel aging, wine experts are invited to taste the wine, and a barrel score out of 100 is assigned. This barrel score acts as an indicator of the potential quality of the wine. At this time, based on the barrel score, the winemaker must decide on two key decisions: (1) the amount of wine to be allocated for sales as futures and (2) the price of wine futures. After one more year of aging, the wine is bottled and is sent to the same set of reviewers to receive a final bottle score, which in turns influences the market price for retail. We present a prescriptive analytical model that incorporates both the uncertain bottle score assigned to the wine and the uncertain consumer valuation of wine futures. Through the analysis of the analytical model, we illustrate the effect of changing the barrel score, the winemaker’s and consumers’ risk preferences, and the degree of consumer heterogeneity, on the winemaker’s optimal decisions and profitability. In addition to the analytical model, the study presents a comprehensive numerical study to further highlights effects of barrel scores on the winemaker’s decisions. The findings from the numerical study illustrate the effectiveness of the analytical model and the potential financial impact of wine futures as tool to help winemaker mitigate quality rating risk.