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iCloud Outlook Add-In Not Working

The iCloud Outlook Add-In that normally syncs contacts and calendars to the Microsoft Outlook app isn't working and isn't showing up in the Outlook desktop app. I'm running the latest stable versions of Windows 11, Office/Microsoft 365 and the iCloud Desktop app. This is despite the add-in being turned on in the Outlook app and the sync option being turned on in the iCloud desktop app. I have attached some screenshots to this post to better explain this. Is anyone else having this issue with iCloud for Windows app? If it is a bug where can I make a report about it?


Thank for the help!


Aaron





Windows

Posted on Aug 16, 2023 3:04 PM

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10 replies

Aug 17, 2023 12:11 PM in response to aaronbacklund

Hi aaronbacklund,


We can recommend taking a look over the tips in the following article: If you can’t add iCloud Mail, Contacts, or Calendars to Outlook


Of particular note is the section:

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 in Outlook 2010 and later to check and turn on the Add-in:
1. Select the File menu.
2. Select Options in the left panel.
3. Select Add-ins in the left panel of the Outlook Options window.
4. 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.
5. Select the iCloud Outlook Add-in checkbox, then select OK.
6. Restart Outlook


Should the issue persist or if you have further questions, contact Apple Support to take a closer look.


Take care.

Aug 18, 2023 7:30 AM in response to aaronbacklund

Hello aaronbacklund,


If this issue continues to occur after following the steps we provided and after reinstalling Windows, reach out to Apple Support next. They would be the best equipped to investigate this behavior more. You can contact them using the last link we previously sent over or by calling the phone number most applicable to you from here: Contact Apple for support and service


Cheers!

Sep 25, 2023 12:30 AM in response to aaronbacklund

Here are some steps you can take to address this issue:

  1. Check for Updates: Ensure that both Microsoft Office/Microsoft 365 and the iCloud Desktop app are up to date. Sometimes, software updates can resolve compatibility issues.
  2. Restart Your Computer: Sometimes, a simple restart can help resolve add-in-related problems. Restart your computer and check if the iCloud Add-In starts working.
  3. Verify Add-In Status in Outlook:
    • Open Microsoft Outlook.
    • Click on "File" in the top left corner.
    • Select "Options" and then "Add-Ins."
    • Make sure that the iCloud Add-In is listed and enabled. If it's disabled, you can enable it here.
  1. Check iCloud Desktop App Settings:
    • Open the iCloud Desktop app.
    • Ensure that the "Mail, Contacts, Calendars, and Tasks" option is selected for syncing.
    • Confirm that your iCloud account is signed in correctly.
  1. Disable Other Add-Ins: Sometimes, conflicts with other Outlook add-ins can cause issues. Try disabling other add-ins one by one to see if the iCloud Add-In starts working.
  2. Reinstall iCloud for Windows:
    • If the issue persists, you may want to try uninstalling and then reinstalling the iCloud for Windows app.


Aug 17, 2023 7:09 PM in response to DerekM87

Hello, DerekM87,


I tried the above steps in your post and from the site and the Outlook Add-In is still not coming up despite it being enabled in Outlook. I think this is a bug with the iCloud app with the most recent update as this didn't happen until recently. I even tried reinstalling the Windows 11 OS on the computer and it even occurred with the clean install of Microsoft 365 and Office.


Any suggestions?


Thanks

Aaron

Aug 25, 2023 2:05 AM in response to aaronbacklund

I am having a similar issue and for me I found that in the outlook account settings that under data files the iCloud account was missing. (See screenshot how it looks vs. how it is supposed to look).



How it is supposed to look like:


When I try to manually add it I get the same result as you:


I've reached out to the apple support and the case was escalated and I will hear back from the technicians in the next couple of days, I will update if I have any noteworthy news or perhaps even a solution here.

iCloud Outlook Add-In Not Working

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