Please try these steps as they may help: Resolve issues between iCloud for Windows or iTunes and third-party security software - Apple Supportīefore you change your security software's setup: We understand that your iCloud Contacts are no longer syncing with Outlook. The only thing that I can think of that has changed is Microsoft sent a out new look for Outlook. I spent 3 hours with Microsoft Help to no avail. I think I've tried everything, but open to suggestions. I've uninstalled the two apple iCloud applications (iCloud and iCloud Outlook), rebooted my machine, installed the iCloud apps, rebooted my machine, logged in my iCloud account, check the box for contacts and calendars with Outlook still closed, rebooted again, opened outlook and nothing. I've rebooted my machine and tried the same thing. I've checked unchecked and rechecked the box on the app for contacts and calendars with Outlook closed. This has happened before and I've been able to restore it. This used to work but in the last couple of weeks it got disabled by Outlook. I'm running Windows 11 and Office 365 up to date version. My iCloud for PC app will not load (sync) Contacts and Calendars with my Outlook.
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