A number of users who sync iCloud and Outlook are having problems with iCloud after installing the Windows 10 Anniversary Update.
If the iCloud addin gets disabled every time you restart Outlook, see iCloud Doesn't Sync for the registry key to force it to always load.
Signing out of iCloud then signing back in should fix the problem. If not. try the steps below.
To fix iCloud and restore syncing:
- Sign out of iCloud
- Uninstall iCloud
- Repair Outlook
- Reinstall the newest version of iCloud (5.2 or higher) and sign in.
If you continue to have problems, you can revert to Office 2016 version 16.0.6868.2067.
- Close all Office applications.
- Right-click on the Start button, choose Command Prompt (Admin). If it's not listed on the right-click menu, click Start, type cmd in the Start Search box, then right-click on Command Prompt or cmd.exe, and choose Run as administrator.
- At the command prompt, type the following command, and then press Enter:
cd %programfiles%\Common Files\Microsoft Shared\ClickToRun
- Type the following command, and then press Enter:
officec2rclient.exe /update user updatetoversion=16.0.6868.2067
- When the repair dialog box appears, choose Online Repair.
- Click Repair, and then click Repair again.
After the repair is complete, you'll need to disable automatic updates. In File, Office Account. Click Update Options, and then click Disable Updates.