Curious to see if this had come up for anyone? I just installed some more of my UAD stuff and licenses on the iLok. Now all my licenses on my iLok (Oxford, Relan, not just UA) are not working and I am getting an iLok Clock Needs Repair sign.
I had this issue too. By plugging the iLok USB into a PC with internet access and running “Synchronize” it kinda started working.
I also had to wait until the newly purchased license on iLok entered its validity period (as the date/time on the transform.engine is somewhat 1-2 days behind and cannot be set manually).