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How to fix icloud for windows syncing icloud calendar and contacts

Jim Maxwell 0 Reputation points
2026-06-03T16:23:19.9833333+00:00

Hello, I have been in contact with Apple regarding an issue with iCloud for Windows where there are no checkmarks on the app dialogue box to sync my icloud calendar and icloud contacts with Outlook. This is occurring on a new Surface Pro that I just purchased. Please see attached for a more detailed explanation and the correspondence with Apple. Note on the last page that they are saying this is an issue with Outlook. Any help would be greatly appreciated!

[Moderator Note: Personal Info Removed]

Outlook | Windows | Classic Outlook for Windows | For home
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  1. Chloe-V 8,080 Reputation points Microsoft External Staff Moderator
    2026-06-04T09:45:44.3866667+00:00

    Hi Jim Maxwell,

    Welcome to Microsoft Q&A forum. 

    Based on the details you shared, if you are using classic Outlook, the iCloud Calendar and Contacts options should normally come from iCloud for Windows rather than from a separate setting inside Outlook.

    Because those checkboxes are not appearing at all in iCloud for Windows on your new Surface Pro, this looks more like an issue with the Apple iCloud integration on that device than a standard Outlook setting that can be turned back on.

    Apple’s guidance also shows that iCloud Calendar and Contacts in Outlook are tied to iCloud for Windows, and Apple’s troubleshooting notes that Outlook compatibility can depend on how Office was installed.

    At this point, I would suggest checking the following:

    • Make sure iCloud for Windows was installed from the Microsoft Store.
    • Confirm Outlook is not the Microsoft Store version of Office. If it is, try uninstalling that build and reinstalling Microsoft 365 desktop apps.
    • Restart Windows, then sign back in to iCloud for Windows and check whether the Calendar and Contacts options appear.

    Please note that this is a user-to-user support forum. Moderators, contributors including external Microsoft employees cannot directly intervene in Microsoft product features or access back-end systems. Our role is limited to providing technical guidance on reported issues, requests, or ideas only.

    Since this is a public forum, we will hide your personal identifiable information, and I have sent that image of yours containing your personal identifiable information in a private message so we can work together to resolve the issue. Also, please check your private message in case you want to share another screenshot to avoid leaking your PII by click on the Private Message button as show below

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  2. AI answer

    2026-06-03T16:23:51.8733333+00:00

    On a new Surface Pro, iCloud Calendar and Contacts will only sync with classic Outlook if a supported iCloud for Windows version is installed and properly registered with Outlook’s MAPI services.

    Use these steps:

    1. Install or update iCloud for Windows to a version that supports Outlook 2016 or later
      • Install the latest iCloud for Windows that includes Outlook support. Apple released iCloud for Windows v 5.1 specifically to add support for Office 2016 and fix earlier integration issues.
      • Download and install from Apple’s page: Download iCloud for Windows.
      • After installation, restart the Surface Pro.
    2. Re‑enable iCloud integration with Outlook
      • Open the iCloud for Windows app.
      • Sign in with the Apple ID.
      • In the iCloud dialog, verify that the options for Mail, Contacts, Calendars, and Tasks with Outlook are now available and can be checked.
      • Select the checkboxes for Calendar and Contacts (and Mail/Tasks if desired), then apply.
    3. If iCloud fails to load in Outlook
      • If, after enabling in iCloud for Windows, Outlook shows an error like:

        “The set of folders cannot be opened. MAPI was unable to load the information service C:\PROGRA~2\COMMON~1\Apple\Internet Services\APLZOD.dll. Be sure the service is correctly installed and configured.”

      • For Outlook 2010, 2013, or 2016 and later, uninstall iCloud for Windows, then reinstall it using the latest installer from Apple’s iCloud setup page: Set up and use iCloud for Windows.
      • Restart Windows and Outlook, then re‑enable the Outlook integration in the iCloud app.
    4. If using Outlook 2007 (less likely on a new Surface)
      • Outlook 2007 requires a registry change to allow unregistered MAPI services such as the older iCloud provider. This is not recommended because it reduces security, but if absolutely required, the documented workaround is:
        • Create or edit the DWORD value AllowUnregisteredMapiServices under: HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\Security
        • Set it to 1 to enable loading unregistered MAPI services.
        • Restart the computer and then Outlook.
      • This workaround is at the user’s own risk and should only be used if explicitly needed.

    Once the correct iCloud for Windows version is installed and Outlook integration is enabled, the checkboxes for syncing iCloud Calendar and Contacts should appear in the iCloud for Windows dialog, and the corresponding folders should show in classic Outlook on the Surface Pro.

    References:

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