A pill dispensing assembly comprises a pill bottle that is securely locked between a base and an attachable sleeve. The pill bottle and base form an enclosure in which pills are stored above a top portion of a dosing mechanism of the base. The top portion of the dosing mechanism comprises a ramp and a rotating arm that carries a pill from a base of the ramp to a position in which the pill will drop through an aperture in a bottom portion of the dosing mechanism into a channel that connects the aperture to a dispensing slot in a housing of the base. The base includes a microcontroller that interacts with a servomotor to control rotation of the arm and thereby the dispensing of a pill. The base also includes a wireless communication interface that enables the dispensing of the pill to be controlled by a remote entity.