Embodiments provide a system and method for a customized alert generation for medication adherence. Medication intake instructions and user data are collected and analyzed to determine an availability model of the user to take the medication. A suggested arrangement for the user to take the medication based on the availability model is determined, and the user is alerted according to the suggested arrangement. The user provides feedback on whether the medication was taken upon receiving the alert, and the feedback trains the availability model to provide an improved suggested arrangement for taking the medication.