Medical devices used in a home setting for treating a variety of chronic diseases lack the ability to convey meaningful information to the patients directly about how they are engaging with their devices in real-time. This research is focused on the development of a monitoring system that addresses this need. For this initial design and testing, the research team applied the technology to a positive airway pressure (PAP) system used in the treatment of those suffering from obstructive sleep apnea (OSA). Data from experimental testing showed results of 93.6% accuracy, 98.7% sensitivity, and 90.9% specificity in the monitoring system detecting events that are typical of issues occurring during standard PAP therapy use. Results indicate this technology can be considered as a viable solution for providing more meaningful information to users about their engagement with their prescribed medical devices.