This paper addresses the optimal placement and sizing of Modular Static Synchronous Series Compensators (M-SSSCs) to enhance power system performance. The proposed methodology optimizes four key objectives: reducing transmission line loadability, minimizing power losses, mitigating voltage deviations, and enhancing voltage stability using the L-index. The methodology is validated on two systems: the IEEE 14-bus test network and a sub-area of the Colombian power grid, characterized by aging infrastructure and operational challenges. The optimization process employs three metaheuristic algorithms—Genetic Algorithm (GA), Particle Swarm Optimization (PSO), and Teaching–Learning-Based Optimization (TLBO)—to identify optimal configurations. System performance is analyzed under both normal operating conditions and contingency scenarios (N − 1). The results demonstrate that M-SSSC deployment significantly reduces congestion, enhances voltage stability, and improves overall system efficiency. Furthermore, this work highlights the practical application of M-SSSC in modernizing real-world grids, aligning with sustainable energy transition goals. This study identifies the optimal M-SSSC configurations and placement alternatives for the analyzed systems. Specifically, for the Colombian sub-area, the most suitable solutions involve installing M-SSSC devices in capacitive mode on the Termocol–Guajira and Santa Marta–Guajira 220 kV transmission lines.