iCloud for Windows add-in stops working in Outlook 2016. This happens about every few months. Currently cannot get it to enable so no calendar or task syncing. Very frustrating. What is a person to do?

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iCloud for Windows add-in stops working in Outlook 2016. This happens about every few months. Currently cannot get it to enable so no calendar or task syncing. Very frustrating. What is a person to do?

iCloud for Windows is very unreliable. I use Outlook 2016 with the iCloud add-in to sync a personal calendar and task list. It switches itself to disabled every so often. Usually, I can enable it and return to normal. Sometimes I have to go to iCloud setup and uncheck the mail, calendar and tasks item, click the Apply button, restart Outlook, and then re-check that item in the iCloud setup and apply it. This will rebuild it in Outlook and return things to normal. This time, neither of those options are working. I seem to be stuck with a desktop machine that will not sync with iCloud. I have a laptop with the same setup working fine. What is up with this iCloud for Windows app? It is very unreliable on a PC running Windows. I find the web browser interface and iPhone interface for updating tasks to be horrible so the only way to do this well is on computer.

Windows, Windows 6

Posted on Dec 21, 2021 9:13 AM

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Answer 1

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888_up Author

Level 1

4 points

Dec 22, 2021 1:43 PM in response to Chris_C1

I finally got it working. Figures crossed but it appears to be working well. I had uninstalled iCloud, signed out, repaired Outlook, in the multiple ways described online but nothing worked. I finally found a tutorial that sent me into the regedit to delete the registry entries for the disabled add-ins. That did the trick. I was finally able to install it and have it stick.

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Answer 2

Chris_C1

Community Specialist

Dec 22, 2021 8:52 AM in response to 888_up

Hello 888_up

Apple Support Communities is a great place for help with the iCloud for Windows app, and we’re glad you were directed here from the Download iCloud for Windows article.

Ensuring your content is syncing as expected is important, and there are great troubleshooting steps that can help with reaching a resolution. If you haven’t already, verifying iCloud for Windows is updated is a great step. If you’re running the latest update, you may have to uninstall and reinstall iCloud for Windows. Those steps can be found in the following article.

Set up and use iCloud for Windows

Let us know how that goes!

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iCloud for Windows add-in stops working in Outlook 2016. This happens about every few months. Currently cannot get it to enable so no calendar or task syncing. Very frustrating. What is a person to do?

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