A work vehicle includes a hydraulic shift control system that enables the work vehicle to smoothly change speeds during a shift and reduce abrupt changes. The hydraulic shift control system may predict undesirable scenarios associated with the abrupt changes. The hydraulic shift control system may utilize configuration data, feedback data (e.g., sensor data), and modeling data to estimate certain operation states and/or parameters, such as engine loads and hydraulic pressures. In response to determining that predicted values may exceed certain thresholds (e.g., maximum load or pressure), the hydraulic shift control system may perform proactive actions to prevent shifting that may cause undesirable outcomes for the work vehicle.