outlook and icloud calendars aren't syncing

Question

outlook and icloud calendars aren't syncing

Carlynn Bock 0

Outlook for Windows on my PC is no longer syncing with my iCloud calendar. If I enter an apt in outlook it shows immediately in my iphone calendar. If I enter a new apt on the iphone it does not show up in outlook. It was working a few days ago. I have loaded the latest icloud iOS updates this morning and refreshed the icloud app for windows several times - shutting off icloud calenar sync with outlook and rebooting and turning back on. Still not working.

I've been trying to fix this all morning. Does msft still offer technical support - I will pay for it. this is crazy

Dena Regas McNeill 0 Reputation points

2026-04-03T20:08:46.6033333+00:00

I have done all of the above. Nothing has worked. I am getting an error code when trying to re-install ICloud for Windows. It gets down to the very last step and I get an error code that has to do with default profile.

I do not have the error code number. But this all has to do with having two profiles in Outlook and neither of them will allow iCloud for windows to work. I have a ticket number and I just noticed that someone cleared it out and said the case was closed and everything was resolved. This is absolutely not true.

Before the MS support tried to help me, my iPhone was synching all calendar entries to Outlook. But Outlook would not send the calendar entries to iPhone. I was having to retype them into my iPhone. Now that MS helped me out, I no longer can see any iphone calendar events in Outlook. So all they did was just cause me further destruction.

******@att.net
Cheryl Warren 0 Reputation points

2026-07-23T12:46:42.6566667+00:00

I am having the same problem

3 answers

Your answer

Dena Regas McNeill 0 Reputation points

2026-04-03T20:08:46.6033333+00:00

I have done all of the above. Nothing has worked. I am getting an error code when trying to re-install ICloud for Windows. It gets down to the very last step and I get an error code that has to do with default profile.

I do not have the error code number. But this all has to do with having two profiles in Outlook and neither of them will allow iCloud for windows to work. I have a ticket number and I just noticed that someone cleared it out and said the case was closed and everything was resolved. This is absolutely not true.

Before the MS support tried to help me, my iPhone was synching all calendar entries to Outlook. But Outlook would not send the calendar entries to iPhone. I was having to retype them into my iPhone. Now that MS helped me out, I no longer can see any iphone calendar events in Outlook. So all they did was just cause me further destruction.

******@att.net
Cheryl Warren 0 Reputation points

2026-07-23T12:46:42.6566667+00:00

I am having the same problem

Answer 1

If your Outlook for Windows is not syncing with your iCloud calendar, here are some troubleshooting steps you can take:

Check iCloud Settings: Ensure that your iCloud account is properly set up in Outlook. Go to the iCloud app on your PC and verify that the calendar sync option is enabled.
Reboot and Refresh: Since you've already rebooted and refreshed the iCloud app, try logging out of your iCloud account in both Outlook and the iCloud app, then log back in.
Update Outlook: Make sure that your Outlook application is updated to the latest version. Sometimes, updates can resolve syncing issues.
Repair Outlook: You can try repairing your Outlook installation. Go to Control Panel > Programs > Programs and Features, select Microsoft Office, and then click on Change. Choose the Repair option.
Check for Conflicts: Ensure there are no conflicting applications or settings that might be preventing the sync. Sometimes, antivirus or firewall settings can interfere with syncing.
Contact Support: If none of the above solutions work, you may want to reach out to Microsoft support for assistance. They do offer technical support, and you can inquire about paid support options if needed.

These steps should help you troubleshoot the syncing issue between Outlook and iCloud calendars.

Answer 2

Hi Carlynn,

Outlook and iCloud sync depends on the iCloud for Windows add-in and Apple’s sync service. After an iOS update or changes in iCloud settings, the integration can break because The iCloud Outlook Add-in gets disabled or corrupted.

Cached sync tokens become invalid after updates.

Version mismatch between Outlook, iCloud for Windows, and Office updates.

Sometimes, Apple’s sync service needs a full reset after major updates.

Steps to fix it

Check iCloud Add-in in Outlook

Open Outlook → File → Options → Add-ins.

At the bottom, select COM Add-ins → Go.

Make sure iCloud Outlook Add-in is checked. If unchecked, enable it.

Repair iCloud for Windows

Go to Control Panel → Programs → Apps & Features → iCloud → Repair.

Restart your PC after repair.

Sign Out and Back In

Open iCloud for Windows, sign out completely, restart your PC, then sign back in.

Update Everything

Ensure Outlook, Office, and iCloud for Windows are fully updated.

In Outlook: File → Account → Update Options → Update Now.

Reset Calendar Sync

In iCloud for Windows, uncheck Mail, Contacts, Calendars, click Apply, then re-check and apply again.

If these steps don’t work, advanced fixes include:

Deleting and recreating the Outlook profile.

Reinstalling iCloud for Windows completely.

Let me know how it goes, Happy to help!

Answer 3

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