Without timely reminders, certain individuals may be highly unlikely to complete various tasks scheduled for completion. For example, medicinal therapy regimen patients often have difficulty in remembering to take their prescribed medications in accordance with care provider specified instructions. By providing a reminder prompt generation system that utilizes machine-learning and/or artificial intelligence to determine appropriate reminder times and modalities for providing automated-prompting notifications to users, the users' adherence to scheduled task completions can be significantly increased.