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I think I figured out what's going on. I have a bootstrap 000000000000.cfg file that my phones load via DHCP option 160 (to set things like the real provisioning server, and set an admin/user password on the device, etc.) which also had the following parameters...

I have never had success using the device.prov.upgradeServer parameter. Polycom forums and documentation seems to state that this only affects the firmware upgrade utility in the web interface, and breaks automatic firmware upgrades via provisioning. I created a pull request a while back to add...