Apple iCloud Add-in Keeps Disabling Itself in Outlook

iCloud Add-in Keeps Disabling Itself in Outlook

you can force outlook not to disable a plugin by change loadbehavior and add it to outlook resiliency list.
It is both done by windows registry (regedit)

open regedit and look for

If you can’t find it try to look for

and set the value for the LoadBehavior to 3 (always load)

Even with this key set, Outlook can some times disable the plugin anyway, you can prevent it by adding another key:

Sources: https://www.slipstick.com/outlook/icloud-sync-failure/

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