@jeremyvdv Spanning tree enables the ports to wait for a period of time between link up/link down before the switch will pass the information to the machine in case there’s a link connected back to itself on the switch.
This up/down time can be around 27 seconds in normal Spanning tree mode. This would explain why during the automated portion the device cannot get a link or IP, but once at the terminal and restarting the networking it will pick it up.
If your network is using spanning tree, if you can do so, disable it, or if not it’s best to use one of the Fast/Rapid stp methodologies as their up/down time is much more significantly reduced.