syncing apple contacts and calendar with MS outlook

Hi @John Hall,

Good day, and thank you for articulating your concern.

On Windows with Classic Outlook, your Apple (iCloud) Contacts and Calendar do not sync automatically with Outlook unless the iCloud integration component is installed and enabled.

After reinstalling Windows 11 and Microsoft Office, that connection is typically removed, which is why syncing stopped.

You can try the following steps to sync your Outlook again with your apple ID:

1/ Download iCloud for Windows

First, you need to re-enable the iCloud–Outlook integration:

• Download or open iCloud for Windows (from Microsoft Store)
• Sign in with your Apple ID. If you have multiple Apple Accounts that you use with iCloud, check that you're logged in to iCloud for Windows with the same account that you use on your other devices.
• Inside the iCloud app, scroll down until you find the “Calendars and Contacts” section and click on the arrow located on the far right.

• Now, ensure that the “Automatically sync your iCloud calendars and contacts to Microsoft Outlook” toggle is active, and then hit the Done button for confirmation.

2/ Make sure that the iCloud Outlook Add-in is on

The iCloud Outlook Add-in transfers your content between iCloud and Outlook. Follow these steps to turn on the Add-in:

• Select the File menu.
• Select Options in the left panel.
• Select Add-ins in the left panel of the Outlook Options window.
• Look at the list of add-ins in the Active Application Add-ins section. If the iCloud Add-in is listed under Inactive or Disabled Add-ins, make sure that Com Add-ins is selected in the drop-down menu next to Manage at the bottom of the window. Then select Go.
• Select the iCloud Outlook Add-in checkbox, then select OK.
• Restart Outlook.

3/ Make sure that iCloud isn’t your default account in Data Files

When iCloud is set as your default account in Data Files, your data won't sync between your devices.

Select File > Info > Account Settings > Data Files.

If iCloud is listed as the default account in the Comments column, select a different account.

Select Set as Default.

After you've tried these steps, restart your computer.

Additionally, please make sure that the date and time settings on your PC are correct.

If you don't use iCloud for Windows, you can follow you can consider set up two-factor authentication for your Apple Account and sign in to Outlook with your Apple Account email address or phone number and an app-specific password.

For reference: It’s now easier to access iCloud Mail, Calendar, and Contacts in Outlook | Microsoft Community Hub

In order to generate an app-specific password, please consult: Sign in to apps with your Apple Account using app-specific passwords - Apple Support

For reference: If you can’t add iCloud Mail, Contacts, or Calendars to Outlook - Apple Support

Note: The 2 links above are a non-Microsoft website. The page appears to be providing accurate, safe information. Watch out for ads on the site that may advertise products frequently classified as a PUP (Potentially Unwanted Products). Thoroughly research any product advertised on the site before you decide to download and install it. 

I hope this provides enough clarity and helps you stay inform with your current situation.

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Thank you for your patience and your understanding. If you have any questions or need further assistance, please feel free to share them in the comments on this post so I can continue to support you.   

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