Can you please provide info on the MAC OSX version you are running and the iOS version on the mobile device.
Can you try doing the same but signing out from True Key and signing back again, it is possible that a network issue might be delaying and eventually timing out the sync between these 2 devices.
if the issue still there, please add here a screen cap that will be helpful.
10.12.5 (Siera) MAC OS
The issue had been going for well over a month. Tried tech support 2 different times. No luck. I tried to uninstall / reinstall the mobile apps a few times.
I exported my password list > uninstalled everything > reinstalled everything, HOWEVER, this time I did not install the OS APP - I just reinstalled the Chrome Extension + Mobile Apps. **fingers crossed** it is working right now. I am afraid to install the OS app.
Good morning, as I said this is probably a sync issue and you have now done all the right things to start form scratch, issue was probably with one of the True Key apps either on the MAC or on the mobile. I don't know if you have tried creating a login/asset on both the MAC and the mobile and see if the sync is done better from one device or from the other. Anyways, you have now started from the beginning resetting everything. I think you can try reinstalling the True Key app on your MAC and we can take it from there.