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Dustin
Dustin, Computer Support Specialist
Category: Microsoft Office
Satisfied Customers: 13534
Experience:  Since Office 2000, Ive been using, repairing and teaching the basics of MS Office to anyone with a need to learn. Worked in The US Army as A Network Switching Systems Operator/Controller .
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I have several similar Dell computers on which I am running

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I have several similar Dell computers on which I am running Office 365 (with all updates installed) and Win 10 64 bit with all updates installed. I am running iCloud on all of them. On all but one, iCloud syncs with Outlook. On one, the Outlook does not upload a new appointment or contact nor download a new item that goes to iCloud from other computers or the iPhone. I have uninstalled Office 365 and iCloud on the machine and reinstalled them. I have done the normal setup of iCloud for Outlook. All the machines have the same build for iCloud and Office 365. Can you tell me why this one machine will not sync with iCloud? Officer 365 on this machine is Version 1707 (build 8326.2107). iCloud is 6.2.2.

Hello,
I am Pete, and I'll be happy to assist with your question today.

This can happen if a port setting is not correct.

Verify that you are using a Windows configuration supported by iCloud.

Customer: replied 1 month ago.
How do you define "Windows configuration"? All my windows installations are 1703 with all current updates and for 64 bit machines. What port setting are you referring to? the port for email configuration or some other port setting?

Outlook requires port 443 access to iCloud to push and fetch updates to and from the iCloud Calendar servers.

Try opening any https:// secure website to test if ports 80 and 443 are accessible...

If you can access secure sites ok, then verify that your iCloud member name is ***** ***** the iCloud Control Panel window on the computer.

Restart the computer if it has not been restarted recently.

Close and reopen the iCloud Control Panel.

Make sure that iCloud is NOT your default account in Outlook - select File > Info > Account Settings > Data Files. If iCloud is listed as the default account in the Comments column, select a different account and click Set as Default.

Make sure that the iCloud Outlook Add-in is active within Outlook.

Have you also tried turning iCloud Calendar off and back on again to see if that helps?

  1. Close Outlook.
  2. Open the Windows Control Panel.
  3. Deselect the checkbox next to Mail, Contacts, Calendars & Tasks, and click Apply. Wait a few seconds, then replace the checkmark and click Apply.
  4. Open Outlook and test to see if the issue has been resolved.


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Pete.
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Customer: replied 28 days ago.
I had to be away from the office for a few days so I am just now back to the issue. I have tried every step, carefully with no change. From my laptop a new apt sync with the iCloud calendar. From my iPhone a new apt syncs with iCoud.com. The two sync with each other. But a new apt on my desktop Outlook does not go to iCloud.com nor the other two. Of course if I turn off iCloud on the desktop and then restart and set up iCloud in Outlook anew and proceed, all the iCloud.com appts are there, but no new ones sync from either direction.

Ok, let me check if the other techs have any idea on this..

Welcome to Justanswer.com, my name is ***** ***** I will do my best to assist you.

What you need is something thats going to allow a real time, two way sync. There are cheap apps that do that.. This is one of the best

https://www.companionlink.com/outlook/

It comes with free technical support, and will keep everything from calendars to contacts in real time sync between outlook for desktop and your idevices.

If you have any further questions, let me know.

I strive to provide great service, and greatly appreciate a 5 star rating clicked and submitted when you are satisfied.. I always answer follow up questions.

Dustin S.

Senior Technician and Network Switching Systems Operator / Maintainer.

Customer: replied 28 days ago.
Because I have a total of 6 devices that I keep my contacts, tasks and calendars sync'd on, I prefer iCloud. And icloud works on 5 of the 6. I am trying to determine why iCloud does not sync with this one when all are on Office 365 with latest udates and all are on Win 10 1703 with latest updates.

So you are sayin you have other windows 10 computers that outlook does sync the calendar entries to icloud and vice versa?

It may be a bit simpler and easier if you and I connect through a secure remote assistance. With that, I will be able to connect to your computer from here and work on repairing the issue personally. This can save a lot of time and if your not very fluent with computer repairs this is the best option.

Our secure remote assistance is guaranteed meaning if I cant solve the issue then you will be entitled to a full refund of all fees. Would you like to try a remote assistance session or would you prefer to continue via written support alone?

Thank you for your response,

Dustin S

Dustin, Computer Support Specialist
Category: Microsoft Office
Satisfied Customers: 13534
Experience: Since Office 2000, Ive been using, repairing and teaching the basics of MS Office to anyone with a need to learn. Worked in The US Army as A Network Switching Systems Operator/Controller .
Dustin and 2 other Microsoft Office Specialists are ready to help you
Customer: replied 28 days ago.
If you are not able to get the problem to sync automatically with iCloud, no charge. right?