Enabling MAC randomization
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Since the grand total of devices in the test is 2 it's difficult to conclude anything.
Does it happen in any neighboroud ? I mean has it been only tested in an enterprise context with special enterprise wifi access point? which version of UT do you use ?
If the problem really interests you, you could enter the lxc android container (sudo lxc-attach --name android -- sh) and use logcat or take a look at the android wifi logs (/data/vendor/wifi/wlan_logs) while disabling/enabling the wifi in the Ui to see if any interesting error message does appear at this time.