After uploading project files, a reboot is sent, and the ESP checks every 2 seconds whether the device is connected again. The maximum time to wait for the reconnection is the reboot timeout (60 seconds by default), if the device is not reachable after the timeout value expires a timeout error is shown.
Please confirm you are using the latest version of Digi ESP for Python:http://www.digi.com/support/productdetl.jsp?pid=3632&osvid=0&s=393&tp=1
Additionally, you may increase the reboot timeout in your device profile within Digi ESP, Device Manager > LAN Connection > Reboot Timeout.
Jun 13, 2019