Upon arrival, he immediately joined the service of King Francis I as a soldier, earning a reputation for courage and great skill on the battlefield. "In a short time he became eminent, and was favoured by the king, who afterwards recommended him to Henry VIII of England, who much valued him, and heaped favours and honours upon him". For his service to Henry, Herbert was granted the estates of Wilton, Remesbury, and Cardiff Castle, and his position as a man of means was secured.