A transmission system for a machine having an engine and a traction device, the transmission system comprising: a first directional clutch configured to transfer power from the engine to the traction device in a first direction; a second directional clutch configured to transfer power from the engine to the traction device in a second direction opposite the first direction; a brake configured to apply a retarding torque to the traction device; a sensor configured to generate a first signal indicative of an output speed of the transmission system; an input device configured to generate a second signal indicative of an operator's desire to shift power transfer directions from the engine to the traction device; and a controller in communication with the first directional clutch, the second directional clutch, the brake, the sensor, and the input device, the controller being configured to: cause disengagement of the first directional clutch in response to the second signal; cause the brake to apply the retarding torque to the traction device; characterized in that the controller is further configured to: determine an error value as a function of the first signal and a target transmission system output speed during application of the retarding torque to the traction device by the brake; selectively increase the retarding torque applied by the brake when the error value increases; and selectively transfer the retarding torque from the brake to the second directional clutch when a value of the first signal is less than a threshold value. a first directional clutch configured to transfer power from the engine to the traction device in a first direction; a second directional clutch configured to transfer power from the engine to the traction device in a second direction opposite the first direction; a brake configured to apply a retarding torque to the traction device; a sensor configured to generate a first signal indicative of an output speed of the transmission system; an input device configured to generate a second signal indicative of an operator's desire to shift power transfer directions from the engine to the traction device; and a controller in communication with the first directional clutch, the second directional clutch, the brake, the sensor, and the input device, the controller being configured to: cause disengagement of the first directional clutch in response to the second signal; cause the brake to apply the retarding torque to the traction device; characterized in that the controller is further configured to: determine an error value as a function of the first signal and a target transmission system output speed during application of the retarding torque to the traction device by the brake; selectively increase the retarding torque applied by the brake when the error value increases; and selectively transfer the retarding torque from the brake to the second directional clutch when a value of the first signal is less than a threshold value. cause disengagement of the first directional clutch in response to the second signal; cause the brake to apply the retarding torque to the traction device; characterized in that the controller is further configured to: determine an error value as a function of the first signal and a target transmission system output speed during application of the retarding torque to the traction device by the brake; selectively increase the retarding torque applied by the brake when the error value increases; and selectively transfer the retarding torque from the brake to the second directional clutch when a value of the first signal is less than a threshold value. determine an error value as a function of the first signal and a target transmission system output speed during application of the retarding torque to the traction device by the brake; selectively increase the retarding torque applied by the brake when the error value increases; and selectively transfer the retarding torque from the brake to the second directional clutch when a value of the first signal is less than a threshold value.