This paper summarizes a joint NASA/Boeing research effort to advance Active Flow Control (AFC) technology to enhance aerodynamic efficiency of a vertical tail. Sweeping jet AFC technology was successfully tested on subscale and full-scale models as well as in flight. The subscale test was performed at Caltech on a ~14% scale model. More than 50% side force enhancement was achieved by the sweeping jet actuation when the momentum coefficient was 1.7%. AFC caused significant increases in suction pressure on the actuator side and associated side force enhancement. Subsequently, a full-scale Boeing 757 vertical tail model equipped with sweeping jets was tested at the National Full-Scale Aerodynamics Complex 40- by 80-Foot Wind Tunnel at NASA Ames Research Center. There, flow separation control optimization was performed at near flight conditions. Greater than 20% increase in side force were achieved for the maximum rudder deflection of 30° at the key sideslip angles (0° and -7.5°) with a 31-actuator AFC configuration. Based on these tests, the momentum coefficient is shown to be a necessary, but not sufficient parameter to use for design and scaling of sweeping jet AFC from subscale tests to full-scale applications. Leveraging the knowledge gained from the wind tunnel tests, the AFC-enhanced vertical tail technology was successfully flown on the Boeing 757 ecoDemonstrator in the spring of 2015.