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IT Support 101: Windows Outlook iCloud calendar does not sync

Updated: May 14

A common problem with Windows Outlook is how the iCloud calendar is not able to sync properly. Let us fix that.

Windows Outlook iCloud calendar does not sync

We know why you are here. You cannot figure out what is wrong with your Windows Outlook iCloud calendar. The invites on your phone do not sync to your computer, and vice versa. You have tried everything, even calling in IT support but they are not able to assist you. We are here to help you today; we are your IT support team.


So let us take your hands and guide you step-by-step through this awful predicament.



Windows Outlook iCloud calendar does not sync

Step 1: Re-check your settings

Windows Outlook iCloud calendar does not sync


Let's make sure your Outlook iCloud calendar for Windows set up correctly for you to sync it. Click on your calendar icon on the bottom left of your Outlook and have a look at the calendars available. Ensure your iCloud calendar option is checked. Which may be obvious, but remember, we are going through it step-by-step. Feel free to skip any step you are confident. But it does not hurt to confirm it.

Windows Outlook iCloud calendar does not sync

Step 2: Refresh iCloud

Windows Outlook iCloud calendar does not sync


Sometimes a quick refresh may sync your Outlook iCloud calendar for Windows. However, this step requires strict adherence. Shut down Outlook entirely and ensure it is not running in the background. You can run 'task manager' by typing it on your start button. Open your iCloud settings from your taskbar at the bottom right corner of your screen, and you should see the image shown here. Untick the 'Mail, Contacts, Calendars, and Tasks' and click 'Apply'. After doing so, you must count to twenty seconds before doing anything else. Once the twenty seconds are over, tick the 'Mail, Contacts, Calendars, and Tasks' again and click 'Apply'. Once you see the changes have applied successfully, do a fresh restart of your computer. Start Outlook.


Step 3: Updates, updates and updates.

Windows Outlook iCloud calendar does not sync

Windows Outlook iCloud calendar does not sync
Windows Outlook iCloud calendar does not sync

Another reason why your Outlook iCloud calendar does not sync often overlooked. Updates, updates, and updates. Especially if your software is substantially outdated, they may no longer be considered secure by the iCloud server and as a result may not be allowed to connect to it. For Outlook, click on 'File' at the top left corner of your screen and in the tab 'Office Account' and proceed to update your Outlook. Start your 'Apple Software Update' and ensure that your iCloud for Windows updated to the latest version. And after doing updates for either or both software. Restart your computer and start Outlook.




Step 4: Check your Data Files settings

Windows Outlook iCloud calendar does not sync

IT Support 101 My Outlook iCloud calendar in Windows does not sync
Windows Outlook iCloud calendar does not sync

Another reason why your Outlook iCloud calendar in Windows does not sync is a simple mistake in your 'Data Files' setting. To get here, click on 'File' at the top left corner of your Outlook and Click on the 'info' tab. Click on 'Account Settings' and from the drop-down menu, click on 'Account Settings'. Here you see the 'Data Files' tab, click on that, and you see a similar image to ours. One of your data files has the word 'iCloud' in its name. Make sure this data file is not set as your default. So which one is the default file you ask? If you can see the black circle with a white tick inside it beside the name, this indicates which file is the default file. If your iCloud account data file s set as default, choose any other data file and click the button 'Set as Default'. Not that is done, shut down Outlook. Restart your computer and Outlook again.


Step 5: Last option to fix it once and for all

Windows Outlook iCloud calendar does not sync

IT Support 101 My Outlook iCloud calendar in Windows does not sync

Still, your Outlook iCloud calendar for Windows does not sync. We are clearly down to our last option here. If this does not fix it, we do not know what will.

Click on 'File' on the top right and proceed to click on 'Options', which should bring out a window as shown above. Click on 'Add-ins' on the left side menu bar. At the bottom, you see Manage and ensure 'COM Add-ins' selected from the drop-down menu. Click on the button 'Go...'.

IT Support 101 My Outlook iCloud calendar in Windows does not sync

Now what you see in the image above. Make sure the 'iCloud Outlook Add-in' box ticked, click OK. Exit Outlook and restart your computer. Start Outlook again. You are welcome.


We are 99.9% sure that this fixes the issue at hand. Your Outlook iCloud Calendar for Windows sync issue should resolve, which happened to a client who was unable to rectify it. Not to toot our own horn, sometimes the right information is critical, and we hope we were able to help you out with your Outlook iCloud Calendar for Windows sync problem.

Thank you for reading 'IT Support 101: Windows Outlook iCloud calendar does not sync' and have a beautiful day ahead.

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