In this study, wind fragility for anchor systems installed at sign structures was developed through Monte Carlo simulation method. The fragility is a conditional limit state probability, presented as a function of the 3-second gust wind speed, based on a relation between statistics of wind loads and anchor system resistances. Advertisement sign attached to concrete wall structure was investigated using probabilistic approach with consideration of anchor type, exposure category, and wind directionality. The results showed that the failure due to tension on anchor bolt was dominant and occurred at a very high wind speed. The fragility methodology described in this paper can be used to develop performance-based design guidelines for advertisement structure in high wind regions as well as to provide information on which to base structural safety or expected loss assessments.