A system includes a medical device that regulates delivery of medication to a user, a sleep detection system configured to generate user status data that indicates sleeping status of the user, and configured to communicate the user status data, and at least one controller that controls alerts associated with operation of the medical device. The at least one controller receives the user status data generated by the sleep detection system, determines, from the user status data, that the user is sleeping, activates a sleep mode alerting scheme of the medical device when it determines that the user is sleeping, and, after activating the sleep mode alerting scheme, controls generation and outputting of alerts associated with operation of the medical device in accordance with the sleep mode alerting scheme.