Accurate evaluation of the failure evolution of the overlying strata after multiple mining actions is of great importance both for the prevention of water disasters and the mining designs. To ensure the safety of mining multiple coal seams, the fracture criterions of overlying strata after mining actions were established on the basis of beam theory as well as the influences of coal seam spacing, face size, and lithology on the increased heights of failure zones after each consecutive mining sequence. A newly developed device, named electric controlled water flow detector, and its detecting procedure, was introduced. In situ investigations were performed in the Gaojialiang and Jinhuagong Mines, China. Results showed that the mining of a lower coal seam does not change the failure evolution of the roof strata of the upper coal seam when the coal seam spacing is large. The larger the mining height of the lower coal seam is, the more fractures the overlying strata of the upper coal seam have, and the larger the height of the failure zone. In addition, the failure extent of overlying strata caused by coal face mining increased with their hardness. It was found that the electric controlled water flow detector can effectively detect the failure evolution during multiple mining actions, with high water plugging effectiveness and detection accuracy.