A system and method for automatic session data transfer between computing devices based on zone transition detection are disclosed. A particular embodiment is configured to: determine if a mobile or wearable computing device is located within a proximity zone around a location of a stationary computing device; establish an authorized wireless data connection with the mobile or wearable computing device via a wireless transceiver; determine if the mobile or wearable computing device is likely departing the proximity zone and if so, upload user session data to the mobile or wearable computing device; and determine if the mobile or wearable computing device is likely approaching the stationary computing device and if so, download user session data from the mobile or wearable computing device.