A system for determining brake shoe effectiveness of a braking arrangement of a train during operation of the train including at least one brake database including braking data and at least one train database including train data. A control system is in communication with the at least one brake database and the at least one train database, and the control system dynamically determines brake shoe effectiveness data based upon the braking data and the train data, where the brake shoe effectiveness data includes the ability of the braking arrangement to retard the train to a specified level.