Systems, devices, and techniques are disclosed for administering and tracking medicine to patients and providing health management capabilities for patients and caregivers. In some aspects, a system includes an injection pen device including a dose setting mechanism, a dispensing mechanism, and an electronics unit to generate dose data associated with a dispensing event of a dose of the medicine dispensed from the injection pen device and time data associated with the dispensing event; a mobile device in wireless communication to receive and process the dose data; and a software application configured to determine a recommended dose based on health data and contextual data associated with a user of the injection pen device, the software application including a learning dose calculator module to adaptively calculate the recommended dose of the medicine based on time-relevant and circumstances-relevant data specific to the user of the injection pen device.