Techniques are disclosed herein for establishing a file transfer connection via wearable devices (e.g., head-mounted wearable devices). A first wearable device generates a gesture-based connection request to connect with a second wearable device. The first wearable device is associated with a first mobile device, and the second wearable device is associated with a second mobile device. The first wearable device sends the gesture-based connection request to a service to authenticate a connection with the second wearable device. The connection is established with the second wearable device in response to receiving an authentication response from the service. The first wearable device directs the first mobile device to transfer a file to the second mobile device.