The current demand for energy efficiency in hydraulics directs towards the replacement of centralized, valve-controlled actuators with individual, throttleless drives. The resulting solutions often require an undesirable sizing of the key components to expand the system’s operating region. Using flow regeneration (i.e., shortcutting the actuator’s chambers) mitigates this issue. Such an option, already stated for individual drives, lacks an in-depth analysis from the control perspective since the dynamic properties are changed (e.g., the natural frequency is decreased to about 60% of the original value). Therefore, this research paper studies a representative single-pump architecture arranged in a closed-circuit configuration. Linear control techniques are used to understand the system dynamics and design a PI-control algorithm that also adds active damping. The outcomes are validated via high-fidelity simulations referring to a single-boom crane as the study case. The results encompassing diverse scenarios indicate that flow regeneration is only interesting in those applications where the dynamic response is not demanding. In fact, the lower natural frequency reduces the system’s bandwidth to about 69% of the original value and affects the closed-loop position tracking drastically. This poor performance becomes evident when medium-to-high actuation velocity is commanded with respect to the maximum value.