Systems and methods for measuring an analyte include devices configured to perform an analyte testing operation. The devices include a wearable electronic device and a remote device operatively connected to each other and each having a processor, the processors cooperating with each other in the execution of program instructions configured to direct the devices in the performance of the analyte testing operation. The wearable electronic device includes a camera configured to generate a video stream and one or more images relating to a user removing a test strip from a vial, producing a bodily fluid sample, and applying the sample to a deposit site of the test strip where the sample undergoes changes in one or more optical properties, the image of which is analyzed to determine a level of the analyte. The wearable electronic device further includes a head-up display (HUD) for providing output messages to the user relating to the performance and status of the analyte testing operation.