A method, and a system configured to perform a method, for customizing user alerts in a medicine administration and tracking system including detecting an alertable condition for which a medicine administration and tracking system is configured to monitor, generating a custom alert for the alertable condition based at least in part on historical data indicating a responsiveness to previous alerts for the same alertable condition, delivering the generated custom alert to a user, determining the user's response to the generated custom alert, and updating the historical data to include the alertable condition, the generated custom alert, and the user's level of responsiveness to the generated custom alert.