New email cannot use iCloud contacts

Question

When composing a new email in classic Outlook, the address fields do not offer my iCloud address list even though the contact tab shows all the contacts. The help topics suggest that I import them, but how does that sync changes?

Answer 1

Classic Outlook for Windows does not natively sync or resolve iCloud contacts in the way expected for an Exchange/Outlook.com address book. Outlook for Mac also does not support iCloud contacts (CardDAV) synchronization, and iCloud contact sync is not supported in Outlook for iOS/Android either, which reflects the general limitation of direct iCloud contact integration across Outlook clients.

Because of this, importing iCloud contacts into Outlook (for example, via vCard → CSV → Outlook contacts) is effectively a one‑time copy, not a live sync. After import, Outlook uses its own local/Exchange contacts folder for address resolution when composing new mail. Any later changes made in iCloud will not automatically sync to Outlook; they would require repeating the export/import process.

To have addresses auto‑complete in the To/CC/BCC fields in classic Outlook, contacts must reside in an Outlook address book (e.g., Contacts folder in the mailbox or PST) that is enabled as an address book. Imported iCloud contacts, once in an Outlook Contacts folder, will work for name resolution, but they will not stay synchronized with iCloud.

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References:

• Microsoft Outlook for Mac compatibility with Apple iCloud
• How do I sync my Outlook contacts to my address book?
• Import contacts from iCloud (vCard .vcf file) to Outlook
• Microsoft 365 operated by 21Vianet: Import contacts to Outlook for Windows

Answer 2

@Peter Hartmaier said

Then the address book shows two with the same name, with the first, the default having nothing and the second on has the names.

Looks like your Outlook Profile is hoarked. But I don't know how to fix it.

Just as a test - Create a new, clean Outlook Profile and add just the iCloud account.
https://support.microsoft.com/en-us/office/create-an-outlook-profile-f544c1ba-3352-4b3b-be0b-8d42a540459d

If that works OK, report back and we'll either start the whole process of migrating to a new Profile, or bring in Microsoft Support to see if they can fix the existing Profile.

The Outlook Data file contact list has nothing in it

That's normal. The Outlook Data file is probably an empty PST file that you added to make the iCloud connector happy. You might be able to remove that PST once you get everything working.
https://www.slipstick.com/outlook/icloud-error-outlook-configured-default-profile/

Add a pst file to the profile and set it as default then restart Outlook. ... After you set up iCloud, you can remove the PST but I often rename the PST "needed for iCloud" and drag it to the bottom of the folder list.

Does it have to be this complicated?

Yes. The whole Outlook Classic/iCloud hookup is pretty much a giant kludge that has "evolved" over the years. i.e. Microsoft keeps patching it to keep up with changes in iCloud.

New Outlook for Windows handles the whole thing much cleaner. But New Outlook has it's own problems.
https://support.microsoft.com/en-us/office/add-or-manage-an-icloud-email-account-in-outlook-4aed8b3d-3c68-4743-8973-f6bd1c56e040#picktab=new_outlook

Answer 3

Did you mark the iCloud Contacts folder as an email Address book?

iCloud Account
Right-click on the Contacts folder -> Properties

Then when you compose a new message, choose the iCloud contacts

Am I even close to the answer you are looking for?

Reference: https://www.outlook-tips.net/tips/icloud-contacts-address-book/

Answer 4

Or to translate, buy a MAC if you want things to work like you think they should.