A method for detecting missed insulin boluses, comprising: receiving, at a computing device, at least one first signal representative of a plurality of glucose measurements for a user and insulin dosing information for the user, the insulin dosing information comprising a time of administration for at least one insulin bolus; analyzing, with a detector of the computing device configured at a first sensitivity level, the plurality of glucose measurements and the insulin dosing information to determine whether the at least one first signal indicates the user missed an insulin bolus following a meal event; generating a user notification when the detector determines the at least one first signal indicates the user missed an insulin bolus; characterized in that the method further comprises: receiving, at the computing device, contextual information regarding the user; reconfiguring the detector, based at least on the contextual information, to detect missed boluses according to a second sensitivity level that is different from the first sensitivity level; receiving, at the computing device, at least one second signal representative of additional glucose measurements and additional insulin dosing information for the user; and analyzing, using the detector of the computing device configured at the second sensitivity level, the additional glucose measurements and the additional insulin dosing information to determine whether the at least one second signal indicates the user missed an insulin bolus following a meal event. receiving, at a computing device, at least one first signal representative of a plurality of glucose measurements for a user and insulin dosing information for the user, the insulin dosing information comprising a time of administration for at least one insulin bolus; analyzing, with a detector of the computing device configured at a first sensitivity level, the plurality of glucose measurements and the insulin dosing information to determine whether the at least one first signal indicates the user missed an insulin bolus following a meal event; generating a user notification when the detector determines the at least one first signal indicates the user missed an insulin bolus; characterized in that the method further comprises: receiving, at the computing device, contextual information regarding the user; reconfiguring the detector, based at least on the contextual information, to detect missed boluses according to a second sensitivity level that is different from the first sensitivity level; receiving, at the computing device, at least one second signal representative of additional glucose measurements and additional insulin dosing information for the user; and analyzing, using the detector of the computing device configured at the second sensitivity level, the additional glucose measurements and the additional insulin dosing information to determine whether the at least one second signal indicates the user missed an insulin bolus following a meal event. receiving, at the computing device, contextual information regarding the user; reconfiguring the detector, based at least on the contextual information, to detect missed boluses according to a second sensitivity level that is different from the first sensitivity level; receiving, at the computing device, at least one second signal representative of additional glucose measurements and additional insulin dosing information for the user; and analyzing, using the detector of the computing device configured at the second sensitivity level, the additional glucose measurements and the additional insulin dosing information to determine whether the at least one second signal indicates the user missed an insulin bolus following a meal event.