Requesting help in re-adding iCloud to Office 365 Outlook Classic on my PC. (Not online Outlook)

Question

Requesting help in re-adding iCloud to Office 365 Outlook Classic on my PC. (Not online Outlook)

Adding iCloud to Windows 365 Outlook Classic

I use Outlook Classic on my Windows 11 PC. I use iCloud to sync my calendar and contacts between my Windows PC and my iPhone 15Pro. All was working well and then it wasn't.

I followed the tip - uninstall iCloud for Windows from MS Outlook.

I can see calendar and contacts on iCloud but I cannot get to sync with Outlook Classic on my PC.

Tips are welcome! Thanks!!

Windows, Windows 11 (26200)

Posted on Nov 19, 2025 3:30 PM

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Answer 1

Top-ranking reply

azaksalmarzur28

Level 4

1,960 points

Dec 9, 2025 10:40 PM in response to MikeLostWithiCloud

To restore iCloud → Outlook Classic sync:

Ensure Outlook is Classic, not “New Outlook.”
Uninstall iCloud completely.
Repair Microsoft Office.
Reinstall Apple’s version of iCloud for Windows.
Re-enable the iCloud Outlook Add-in.
Make sure the iCloud .ost file appears in Outlook.
Delete corrupted iCloud cache files if needed.

Once done, your Contacts + Calendar will reappear in Outlook and sync bi-directionally again.

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Answer 2

Jan 3, 2026 11:59 AM in response to azaksalmarzur28

Thank you so, so very much! BUT, when I go to the Apple site to reinstall iCloud for Windows, it redirects me to the Microsoft site to download iCloud for Windows. How do I find the Apple version?

I so appreciate your help.

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Answer 3

Jan 3, 2026 12:31 PM in response to MikeLostWithiCloud

Good news!! The steps you suggested WORKED - even with me using the Windows download for iCloud.

The keys must have been - removing the existing iCloud version and repairing Windows 365.

YEAH - thank YOU!

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Requesting help in re-adding iCloud to Office 365 Outlook Classic on my PC. (Not online Outlook)

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