A diabetes management system includes a handheld medical device, a mobile computing device, and a diabetes management application. The handheld medical device is configured to determine, in response to a port receiving a test strip, whether an auto-send feature is enabled on the handheld medical device, determine whether the handheld medical device is paired with a mobile computing device, and selectively instruct a wireless transceiver to establish a wireless connection and communicate a glucose measurement and identifying information to the mobile computing device. The mobile computing device is configured to execute the diabetes management application. The diabetes management application is configured to process a plurality of glucose measurements and identifying information associated with each of a plurality of glucose measurements.
