Syncing Outlook and Apple Contacts through iCloud.

Hey there CBW17,

Thanks for reaching out to Apple Support Communities. We're happy to provide some assistance.

Let's make sure you're following the actions in this article to sync your Outlook Contacts to iCloud for Windows:

Use iCloud for Windows to synchronize calendar and contacts with Outlook

"You can use iCloud for Windows to synchronize your calendar and contacts between your iOS device and Outlook. To install iCloud for Windows, use the following steps. 

1. Download and install iCloud for Windows.
2. After installation, launch the iCloud app and sign in with your Apple ID and password.
3. In the iCloud app, select the option to sync Contacts and Calendars, then click Apply.
4. Once the setup has finished, launch Outlook. Your iCloud contacts and calendars should now be synchronizing with Outlook."

If the issue persists, let's make sure your PC is up-to-date. If it is updated, let's restart your device. Restarting your PC and making sure it is updated can resolve many unexpected issues. If you're unsure how to do this, please reach out to Microsoft for assistance.

If you continue to experience issues after following the aforementioned information, please reach out to Microsoft for assistance on that error message

Have a great day!

CBW17, Thank you for keeping us posted. Have you had the chance to try the steps in the article below from Microsoft's Help Center page?

Synchronize Outlook and Apple iPhone or iPod touch contacts

If yes, please reach out to us here so we can take a closer look into the issue: Get Support

Take care!