In some cases, it might be necessary to temporarily remove your security software to isolate an issue. If you still have trouble after you test your connectivity, your security software could be interfering with your computer's connection with iCloud for Windows or iTunes. If you’re having issues using AirPlay, Home Sharing, iTunes, or Remote, test the connectivity between the computers or devices in your house. They should be connected to the same network and subnet in order to function properly.Check your hosts file to make sure that it's not blocking iTunes from communicating with Apple's servers.If you have more than one type of security software installed, you might experience performance issues. Make sure that you only have one type of security software installed.Make sure that you set up Windows Hello.Make sure that you have the latest software on your Mac or on your PC.

Update to the latest version of iCloud for Windows or update to the latest version of iTunes.

Learn how to update these settings on a Mac or on a PC.

Make sure that the date, time, and time zone are set correctly on your computer.

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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