A vertical launching system(VLS) is a system for holding and firing missiles on surface ships. When a missile is launched in VLS, relative motion between canister and missile and drag force induced by wind can cause initial unstability of a missile. Thus dynamic analysis of initial behavior of vertically launched missile should be performed to prevent collision with any structure of a ship. In this study, dynamic analyses of initial behavior of vertically launched missile are performed using Monte-Carlo simulation, which relys on random sampling and probabilistic distribution of variables. Each parameter related with dynamic behavior of a missile is modeled with probability variables and Recurdyn, a commercial software for multi body dynamic analysis, is used to perform Monte-Carlo simulation. As a result, initial behavior of a missile is evaluated with respect to various performance indexes in a probabilistic sense and sensitivity of the each parameters is calculated.