Factors affecting the cost of portfolio insurance can be classified into two categories: (1) uncontrollable factors, such as risk free rate, equity risk premium, and market volatility; and (2) controllable factors, such as floor return, coinsurance, portfolio risk (β), and protection horizon. This paper applies the principle of option replication to the Taiwan Stock Market, and focuses on the impacts of controllable factors on the cost of portfolio insurance, which can be measured by the reduction of long-run arithmetic (or geometric) average return and the loss of upside captures. Results indicate that the cost of implementing portfolio insurance in the Taiwan Stock market is negative if the time horizon of portfolio insurance is one year, i.e., excess return relative to the buy-and-hold (uninsured) strategy. However, as the time horizon increases, the cost of portfolio insurance becomes positive.