The expected sliding distance for the lifetime of a caisson breakwater has a limitation to be used as the stability criterion of the breakwater. Since the expected sliding distance is calculated as the mean of simulated sliding distances for the lifetime, there is possibility for the actual sliding distance to exceed the expected sliding distance. To overcome this problem, the exceedance probability of the allowable sliding distance is used to assess the stability of sliding. Latin Hypercube sampling and Crude Monte Carlo simulation were used to calculate the exceedance probability. The doubly-truncated normal distribution was considered to complement the physical disadvantage of the normal distribution as the random variable distribution. In the case of using the normal distribution, the cross-sections of Okgye, Hwasun, and Donghae NI before reinforcement were found to be unstable in all the limit states. On the other hand, when applying the doubly-truncated normal distribution, the cross-sections of Hwasun and Donghae NI before reinforcement were evaluated to be unstable in the repairable limit state and all the limit states, respectively. Finally, the shortcoming of the expected sliding distance as the stability criterion was investigated, and we reasonably assessed the stability of sliding of caissons by using the exceedance probability of allowable sliding distance for the caisson breakwaters in Korea.