iCloud Contacts and Calendar on Outlook 365 PC

Follow-up: I installed an older version of iCloud for Windows (version 7.1) and got it working again. However, as mentioned in my original post, opening the calendar "tab" of Outlook is now painfully slow. Just timed it at 7.5 seconds to fully render. Without iCloud sync activated, it's more like 1.5 seconds.

This could have been the issue as I tried the 'New' or 'pre' outlook. I reverted almost straight away as didn't have the time to go through the rigmarole to re-establish .pst files and it had totally 'discarded' all non MS email addresses, including iCloud.

I used the iCloud app, stopped and restarted 'Contacts and Calendars With Outlook' and am back up.

One thing to note about Contacts with iCloud, the Current View should be 'Phone'. It gives you the List view (in Office 2019 anyway), The Outlook 'List' view shows no contacts.

All Above with Windows 11 Pro v 22H2: 22631 and MS Office Pro Plus 2019 - Outlook v 2304 and iCloud v 14.1.108.0.

A little tip to both Microsoft and Apple - 'If it ain't broke, don't fix it!'

Hello MKHouston,

Welcome to Apple Support Communities. 

We understand that your iCloud Contacts are no longer syncing with Outlook. We are happy to help.

Please try these steps as they may help: Resolve issues between iCloud for Windows or iTunes and third-party security software - Apple Support

"Things to check first

Before you change your security software's setup: 

• Make sure that the date, time, and time zone are set correctly on your computer. Learn how to update these settings on a Mac or on a PC. 
• Log in to an administrative user account, not a guest account. Learn how to do this on a PC. 
• Update to the latest version of iCloud for Windows or update to the latest version of iTunes.
• Make sure that you have the latest software on your Mac or on your PC.
• Make sure that you set up Windows Hello. Learn how to set it up. 
• Make sure that you only have one type of security software installed. If you have more than one type of security software installed, you might experience performance issues.

Test your connectivity

1. Check your hosts file to make sure that it's not blocking iTunes from communicating with Apple's servers.
2. If you’re having issues using AirPlay, Home Sharing, iTunes, or Remote, test the connectivity between the computers or devices in your house. They should be connected to the same network and subnet in order to function properly.

Test your security software

If you still have trouble after you test your connectivity, your security software could be interfering with your computer's connection with iCloud for Windows or iTunes.

In some cases, it might be necessary to temporarily remove your security software to isolate an issue. Some Internet security apps don’t uninstall completely, so you might need to download and run a cleanup utility for your security software for it to be completely removed.

Work with your security software provider to allow the complete list of ports and services that Apple products use or if you need help with uninstalling their software."

Let us know if you have further questions.

Take care.

Hi Everyone - I followed this from the Microsoft side, as I got a new Windows 11 notebook, and had all of the problems described above. The Microsoft side describes in detail how to roll back to the very old version of ICloud for Windows, but it also documents more of the root cause problem, which has to do with registry keys. They show how to edit the keys, and in so doing, getting the current version to work.

https://answers.microsoft.com/en-us/outlook_com/forum/all/icloud-contacts-and-calendar-not-working-with/85a8a376-9773-4703-9d4b-4f179494c4da?page=1&messageId=c1cd0eaa-beba-4852-b2bb-c0a6ea1805d9

I personally am not comfortable operating at editing registry keys, so I just did the rollback, which works great.

We now have a lot of posts on both the Apple and the Microsoft support sites, and even someone on this site who said Apple understands the root cause problem.

This is a "marquee feature" of ICloud for Windows and it must be acknowledged, fixed, and fully supported!!!

I am truly blown away by Apple (and Microsoft's)unwillingness to prioritize this. Let's all raise our voices to both companies - Once known, this will keep a lot of people from Windows 11. (I have four other machines running on 10, and I won't migrate them until this is fixed) We all pay a yearly fee for Microsoft 365, and ICloud support. Without this fix it, they have lost significant value on Windows 11.

Please be vocal with both Apple and Microsoft Thanks!!

Other posters have had success with previous version of iCloud for windows 7.21.0.23 (see here and in MKHouston's post above ).

[Link Edited by Moderator]

I have a similar issue. I have always used iCloud for Windows calendars as an essential family organisational tool and recently it just 'stopped'.

I am on Office 365. The add-in is showing in the COM Add-Ins but has vanished from the Outlook taskbar. It was there last week so either a 365 or iFW update has broken it beyond repair. I have reinstalled all a million times and tried every fix possible (reg / default folders / etc etc etc). Nothing. The calendars are more important to me than outlook so I may have to cancel 365 completely and given my Apple household I may switch back to Mac.

The only ugly fix I have found so far is that the Windows Calendar app will allow you to load up your iCloud calendars and I am hoping thats not their permanent answer :(

I'm seeing the exact same issue with iCloud for Windows 14.2 and Outlook 16.16626.2000. And I have not switched on the "New Outlook" (too many bugs and issues). I've also tried all the troubleshooting steps detailed in this thread. Nothing seems to be working. Honestly, when it did work, the calendar was so slow to load that I frequently disabled the feature. But I digress. I heard somewhere that the PC, Mac and Web interface for Outlook will all have the same look and capabilities at some point in the future and that the new version will have native support for iCloud. I wonder if the incremental updates on the road to achieving that Nirvana have broken the iCloud interface. That would be entirely on Microsoft. As for the built in compatibility with iCloud, I'll believe it when I see it. And we're probably a pretty long way off from that based on the SLOW rollout of new features in Outlook. They don't even have Contact Lists working yet in the Mac client and that's one of the most fundamental requirements of any email app (and it's been that way for at least a year, now). I'm going to keep plugging away at attempted fixes, but I think we're probably stuck with this until Microsoft and/or Apple issue updates to address the breakdown.

I've just seen that and, as you say, wonder if that has introduced a compatibility problem for the iCloud add-in on the legacy Outlook.

I also have problems this morning (28/05/2023) with iCloud using Windows 11 and Outlook 2019.

It works for a few months then stops. Have to reinstall and then we go through the cycle again.

This seems a continual battle between Apple and Microsoft. I expect they will blame each other, but please for your customers sake can you get this sorted out.

Hi,

I am trying to reinstall iCloud Calendar on my Outlook Microsoft 365 (Windows) but, even though the iCloud add-in is activated and Contacts and Calendars is checked, it is still not showing iCloud in Outlook and my calendars are not being imported.

Does anyone have any suggestions please? I have also tried uninstalling and reinstalling iCloud and Outlook multiple times but just not working. Is this an issue with the latest Outlook update?

Thanks.