A theoretical analysis of the sliding of a Cassie-Baxter droplet on a microstructured surface is conducted. The conventional theory based on the force balance has been frequently used to predict the sliding condition of the droplet; however, the sliding condition cannot be precisely determined because the theory requires the available ranges of the contact angles at the rear and front ends of the droplet. In this study, by calculating the droplet shape and examining the stability of a droplet at every possible pinning point, we propose a new theoretical model that can predict the sliding condition of a two-dimensional (2D) Cassie-Baxter droplet without any a priori measurement but using only the surface information. With the proposed theory, we answer two open questions in sliding research: (i) whether the sliding initiates with front end slip or rear end slip and (ii) whether the advancing and receding contact angles measured on the horizontal surface are comparable with the front and rear contact angles of the droplet at the onset of sliding. Additionally, a new droplet translation motion mechanism promoted by a cycle of condensation and evaporation is suggested, which can be further utilized for precise droplet transportation. Finally, the theoretical results are validated against the 2D line-tension-based front-tracking method (LTM), which can seamlessly capture the attachment and detachment between the droplet and the textured surface.