The private Wi-Fi address feature introduced in iOS 14 causes your device to try to connect to the network with a randomized MAC address.
Because device registration on Cortland-Wifi is based on MAC address, having this feature enabled would cause your device to try and re-register every time you connect to the network.
Users who connect their devices to Cortland-wifi should disable this feature. Instructions from Apple can be found here:
https://support.apple.com/en-us/HT211227