problem connecting Outlook with iCloud contacts

Hi Gary Shepherd,

Welcome to Microsoft Q&A forum. 

Based on your description, it sounds like calendar syncing is working again, but contacts are still missing in Classic Outlook. Unfortunately, contacts don’t sync the same way as calendars subscribed “from the Internet.” To restore contacts syncing, iCloud for Windows must be configured to sync Contacts and Calendars to Outlook so Outlook can generate the dedicated iCloud Contacts folder (separate from “My Contacts”).

• Close Outlook completely.
• Open iCloud for Windows on the PC and sign in with the same Apple ID used on the iPhone/iPad.
• In iCloud for Windows, turn on Contacts and Calendars and enable the option to automatically sync iCloud calendars and contacts to Microsoft Outlook, then select Apply/Done to finish setup.
• Reopen Outlook and go to People (Contacts). Look for an iCloud Contacts folder (or Contacts – iCloud) separate from My Contacts.

Important: Contacts won’t sync by adding a folder under “My Contacts” or by using an Internet calendar link — the iCloud Contacts folder appears only after iCloud for Windows successfully integrates with Outlook.

If “iCloud Contacts” still doesn’t show up:

• In iCloud for Windows, turn Contacts & Calendars off > Apply > turn it back on > Apply, then restart Outlook and check again
• If it still fails, sign out of iCloud for Windows and sign back in, then open Outlook again.
• As a last step, uninstall and reinstall iCloud for Windows, then repeat the setup steps above.

Please feel free to let me know if you have any further updates, thanks.

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Contacts must be synced through the iCloud for Windows integration rather than by adding an Internet calendar link.

To re-establish contact sync between Outlook on Windows and iCloud:

1. Confirm iCloud for Windows is installed and signed in
   • Open the iCloud for Windows app on the PC.
   • Sign in with the Apple ID used on the iPhone/iPad.
2. Enable Contacts and Calendars sync in iCloud for Windows
   • In the iCloud app, make sure Contacts and Calendars is checked.
   • Click Apply.
   • This is what creates the special iCloud contacts store and calendar folders in Outlook; they do not appear via right‑click → Add folder.
3. Open Outlook and verify iCloud folders
   • Start Outlook after applying the iCloud settings.
   • In the People (Contacts) view, look for an iCloud contacts folder or address book separate from "My Contacts".
   • New contacts added in that iCloud contacts folder should sync with the iPhone/iPad.
4. If iCloud was installed before Outlook or is corrupted
   • Uninstall iCloud for Windows.
   • Reinstall the latest supported iCloud for Windows version, then repeat steps 1–3 so it can correctly add the iCloud Mail, Contacts, and Calendars integration for Outlook.

The key point is that iCloud contacts do not sync by right‑clicking "My Contacts" or adding an Internet calendar. They appear as a separate iCloud contacts folder once Contacts and Calendars sync is enabled in the iCloud for Windows app and Outlook is restarted.

References:

• Use iCloud for Windows to synchronize calendar and contacts with Outlook
• iCloud for Windows 5.1 supports Outlook