I have not checked what my iMac is saying: Where would I check this ?
Anyway I can solve and reproduce the USB problem:
I have tried again to transfer files without success.
So I decided to install android debug bridge and switch on USB debugging.
Once I switched on USB debugging under Developer options:
File Transfer is working again
So I switched off USB debugging and File ransfer kept working.
However after rebooting the phone, I cannot transfer files anymore until I switch on USB debugging.
I hope this helps.