A system and method of controlling a clutch fill command based on the hydraulic state of an oncoming clutch is provided. A vehicle includes a hydraulically-actuated oncoming clutch that is configured to engage during a shift event from one operating mode of the vehicle to another. A controller is configured to generate a clutch fill command at an initial time such that completion of the clutch fill command is synchronized with an identified speed profile of the oncoming clutch. The oncoming clutch defines a real-time hydraulic state when the clutch fill command is generated. The controller is configured to generate a real-time acceptable speed margin for the oncoming clutch based at least partially on the real-time hydraulic state of the oncoming clutch. The controller is configured to cancel the clutch fill command if a real-time speed of the oncoming clutch is outside the generated real-time acceptable speed margin.