The paper presents the DORA (Dynamic Optimal Random Access) algorithm for vehicle-to-roadside (V2R) communications, addressing optimal transmission policies for upload scenarios in high-density vehicular traffic. It formulates the problem as a finite-horizon sequential decision-making challenge solved using dynamic programming and demonstrates significant performance improvements over existing heuristics through simulations. The algorithms developed achieve minimal costs and higher upload ratios, demonstrating a significant advantage particularly in varying traffic densities.