Intelligent (smart) tracking accessories for a medicine dispensing device, such as an injection pen or pen device, are described. A smart tracking accessory in the form of a smart cap for a medicine dispensing device, such as an insulin pen, is configured to protect the needle of the dispensing device and the medicine contained therein when the device is not in use. The smart cap may detect the presence of the medicine dispensing device, detect an activation event such as removal from the medicine dispensing device, inform the user whether it is safe to administer a therapeutic dose of medicine, and log occurrence of the dosing event.