A method of facilitating delivery of a discretionary dose of insulin to a user includes: enabling the user or a caregiver to specify, via a computer-based user interface, parameters associated with a discretionary delivery of insulin that may be delivered to the user; subsequently receiving data that represents the user's glucose level during a period of time associated with the discretionary delivery; automatically determining, with a computer-based processor, based on the received data, if, when and how much discretionary insulin should be delivered to the user during the period of time associated with the discretionary delivery; delivering insulin to the user during the period of time associated with the discretionary delivery according to the automatic determination; and delivering insulin to the user with the insulin delivery device according to a non-discretionary insulin delivery schedule unless a discretionary insulin delivery mode has been triggered.