Abstract: Systems and methods herein allow a monitored individual to monitored by a monitoring individual remote therefrom. The systems and methods allow the monitoring individual to define initial configuration settings by completing an on-line questionnaire. The monitored individual is then conditioned to use hardware components of the monitoring system based on these initial configuration settings, and then the system continues to self-learn and modify generated prompts to the monitored individual based on continued use and/or non-use of the hardware by the monitored individual.