Concepts and technologies disclosed herein are directed to the optimization of over-the-air (“OTA”) file distribution for connected cars based upon a heuristic scheduling algorithm. A schedule provided by the heuristic scheduling algorithm is designed to distribute OTA data flow to connected cars over the network (geographically) and over a scheduling time horizon (timely), and is capable of reducing the negative impact of OTA file updates on overall wireless network performance. This schedule is created based upon historical statistics associated with connected car driving patterns and simulations of connected car-specific OTA traffic over the network. By leveraging connected cars that connect to different cells at different times based upon driving patterns, the heuristic scheduling algorithm is effective in reducing OTA impact on the network.