A programmable pill box assembly includes a pill box that has a plurality of compartments therein for containing pills. A plurality of doors is each hingedly coupled to the pill box. Each of the doors is aligned with a respective one of the compartments for opening and closing the compartments. A sensing unit is coupled to the pill box to sense when each of the doors is opened or closed. A transmission unit is removably coupled to the pill box and the transmission unit transmits an alert signal when the sensing unit senses that a respective one of the doors has not been opened at a predetermined time. A bracelet is worn on a wrist of the user and the bracelet is in wireless communication with the transmission unit. The bracelet vibrates to remind the user to take the pills in one of the compartments in the pill box.