iCloud Outlook Add-In Not Working

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.

• Get Support

Take care.

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!

Thank you zoopak for summarising the trouble shooting steps outlined here: If you can’t add iCloud Mail, Contacts, or Calendars to Outlook - Apple Support

These were the first steps tried by both the OP and myself as can bee seen above. Unfortunately we are well beyond this point, as outlined in the previous posts.

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.

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.

The Apple technicians got back to me. It seems this issue is caused by Windows Update from early August (Build 22621.2283 or the Outlook update to Version 2307). Unfortunately, there is no solution, the fix will most likely need to come from Windows in a future update.

Thank you. I can confirm it does work now.

For people using business or enterprise computers where uninstall & reinstall is not an option, there is a way to reset the iCloud program through the applications tab in the systems settings of the computer. After this iCloud needs to be set up again, but it should work, at least it did for me.

You might need to create an App Specific Password from within your Icloud account for Outlook. It worked for me. It is in your Icloud Account settings.