Systems and methods are provided for optimizing basal administration timing in a standing basal insulin regimen of a subject. The regimen specifies a total amount of basal insulin medicament, one or more basal injection event types for a recurring period, and an apportionment of the total amount of medicament between the injection event types. Time stamped glucose measurements of the subject are obtained over a past time course comprising a plurality of instances of the recurring period. When the glucose measurements satisfy a stop condition, a recommended adjustment is determined that comprises a change in the number of injection event types in the regimen and/or a change in the apportionment of insulin medicament between injection event types. The recommended adjustment is communicated to the subject for manual adjustment of the regimen, an insulin pen charged with delivering the regimen to the subject, or a health care practitioner associated with the subject.