Not sure what iOS version it was in but Apple did have a couple of bugs with the randomization when it was first introduced - the current iOS version is 14.6.   If you're getting IP address conflicts then that is because the MX is seeing the same IP address being used by two separate MAC addresses. And this is exactly what Apple did (no, it wasn't intentional, well not so far as they admitted). When they first introduced the MAC randomization on a per SSID basis there were situations where (I believe it was ARP requests) were responded to with the real MAC address, and not the randomized MAC address, whereas normally it responded with the randomized address. And this makes the MX 'think' there is an IP address conflict, although there actually isn't.   The only way I believe you can confirm this is through packet captures and compare MAC addresses in the capture (for the same IP address) with those on the iOS devices, to see if the different MAC addresses are actually on the same device.    EDIT: Might also be worth reducing your DHCP lease times, as the randomized MAC address will likely rotate every 24 hours too. ... View more