I have a laptop with the same setup working fine. I seem to be stuck with a desktop machine that will not sync with iCloud. This time, neither of those options are working. This will rebuild it in Outlook and return things to normal. Sometimes I have to go to iCloud setup and uncheck the mail, calendar and tasks item, click the Apply button, restart Outlook, and then re-check that item in the iCloud setup and apply it. Usually, I can enable it and return to normal. It switches itself to disabled every so often. I use Outlook 2016 with the iCloud add-in to sync a personal calendar and task list.
What is a person to do? iCloud for Windows is very unreliable. Currently cannot get it to enable so no calendar or task syncing. ICloud for Windows add-in stops working in Outlook 2016.
