iCloud problem

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Outlook version
Outlook 2016 32 bit
Email Account
My friend's computer upgraded itself to Windows 10 and iCloud stopped working with Outlook. I uninstalled it and reinstalled the new version, but when she goes to sign in it says "An error occurred during authentication". The error is different than the error you would get if the password or login were incorrect.

I think it is related to the new version of icloud that was just released. There seems to be a lot of reported issues here:
Community: iCloud on my PC | Apple Support Communities
But none of them have any resolution.

The error occurs after the reboot that is required after the icloud install. Outlook is not opened yet. When I do open Outlook, it shows no sign of iCloud.
Do you have any ideas?

I could not sign out, as it would never let me sign in.

The version is the latest version, I just downloaded it. Programs and Features says it is, while on the icloud community I see it referred to as 10.2, so not sure.

What I've tried so far:
I uninstalled all Apple software, including iCloud. (iTunes was not present, the rest of them I removed).
Then reinstalled iCloud, rebooted.
Open iCloud, try to login, get the same error as before, "An error occurred during authentication. Please try again." Tried it again with firewall off, no change.
I know the login is correct, I can log in to the icloud website.

Also if I try to log in to the icloud control panel with an intentionally incorrect password, it gives me the usual "Your Apple id or Password is incorrect" message, so this authentication error is something different. I posted an image of the error message with this post.



  • icloud error.PNG
    icloud error.PNG
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Last edited:
This problem only started happening when the computer updated to Windows 10, but also it seems like a new version of iCloud was released last week too.
10.2 is probably the iTunes version (but i thought it was into v11 now) , 5.2 is the iCloud version. I'll install it and see if i can repro.
My friend had AppleCare so I suggested she let them give it a shot. The senior representative she got on with worked diligently for over an hour, doing nothing particularly surprising, could not get it going, and escalated it to the engineering team or some such thing, they will get back to her.

I decided to give it a shot again. I went in Outlook and disabled every addin that did not seem necessary. I also figured I'd try the initial iCloud login with Outlook closed. Not sure which thing it was that fixed it, but then it logged in no problem. We rebooted as a test, it still works.

One interesting thing is that the Apple guy always installed Apple software by right clicking>run as Admin. Not sure why, but I will try to keep that in mind in the future. He also said iTunes is required in order to run iCloud, which I had never heard.
After three weeks of tearing my hair out I finally FIXED THE **** THING!!! YAY!!!!!!!!!!!!

The secret was uninstalling the current version and going back to an earlier version of icloud for Windows. (I used 3.1). You can find the archived version of earlier versions on the net. Just google it. It now works fine.
The secret was uninstalling the current version and going back to an earlier version of icloud for Windows. (I used 3.1). You can find the archived version of earlier versions on the net. Just google it. It now works fine.

this only works if you use older versions of windows and outlook - if you upgrade either, you'll need to use a newer version.
If you try to save again from the iPad into one of the other iCloud slots, does that resolve things for you? You could also try rebooting both devices.
I just ran into this problem with Windows 10 and iCloud for Windows (whatever the latest versions were as of September 2019). I have no reason to believe the problem was caused by any particular update, though.

The only thing that fixed it for me was to "Repair" (didn't actually have to uninstall) iCloud for Windows; it asked me to restart and I did. After that I didn't have the "An error occurred during authentication. Please try again." problem anymore.
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