A system managing health-related issues (e.g., diabetes) includes a measurement device to measure a health characteristic and a processing device communicatively coupled to the measurement device. The processing device receives the measurement from the measurement device. The processing device includes at least one memory device, a processor, and a user interface. The at least one memory device stores the one or more measurements and computer-readable instructions for a healthcare application. The processor executes the healthcare application. The health care application displays and receives, via the user interface, supplemental health data in association with the one or more measurements. The healthcare application allows a user to input the supplemental data according to adherence burst prompting, measurement and logging prescription, retroactive logging, and/or data display with an electronic calendar. The healthcare application may prompt the user to take a measurement and to input the supplemental data according to these features.
