Techniques are disclosed herein for establishing a file transfer connection via wearable devices (e.g., head-mounted wearable devices). A service executing on a cloud platform receives a connection authentication request including authentication data from wearable devices, each associated with a mobile device. Upon validating the connection authentication request, a file transfer connection between the wearable devices is established. The service receives a request from one of the wearable devices to transfer a file maintained by an associated mobile device to another mobile device. Upon validating this request, the service sends an authorization to transfer the file.