A pill dispensing system comprises a pill dispensing assembly and an application executing on a device. The pill dispensing assembly includes an enclosure that stores one or more pills, a dosing mechanism, a wireless communication interface, and a microcontroller that is connected to the dosing mechanism and the wireless communication interface, the microcontroller being configured to activate the dosing mechanism to dispense a pill from the enclosure in response to the receipt of a control signal via the wireless communication interface. The application is configured to send the control signal to the microcontroller via the wireless communication interface in response to an interaction therewith by a user. Pill dispensing event data may be collected by the application and stored in a remote backend database and uploaded at a user's discretion to a physician and/or pharmacists electronic health record (EHR)/EMR system.