The purpose of this paper is to propose a methodology of implementing contingent portfolio insurance. Specifically, based on the filter rule to judge while the market is bull or bear, we investigate the effect of contingent portfolio insurance on the portfolio of ”Taiwan Stock Exchange Capitalization Weighted Stock Index.” The performance of the contingent portfolio insurance is compared with those of the standard portfolio insurance and the buy-and-hold strategy. Results indicate that, for filters 1% to 9%, the contingent portfolio insurance outperformed the other two strategies in various investment horizons for a 20-year sample period.