Outlook no longer working with iCloud

When I reboot in Window 10 and then launch Outlook, to enable iCloud, I always must go to FILE -> Options -> Add-ins -> Hit the "GO" button, and the select iCloud Outlook Add-in. This procedure itself is a pain, and I wish Apple and M/S would work together to get this more streamlined. When I do that, iCloud seems synced to Outlook.

However, I noticed this week that this no longer works and nothing is syncing up.

I uninstalled outlook and reinstalled it.

Still the same result!

What happened?