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ReginaUser Author

Level 1

27 points

iCloud for Windows 10/11 Keychain authentication issue

Has any one found a solution to this problem?

I am able to login to my iTunes account with no issues using two factor authentication. The problem is that when I attempt to Approve it goes through the first login (Apple ID / Password) fine. I then get my 2 step authentication code on my iPhone and enter it. After a while it times out telling me "There was an error connecting to the Apple ID server".

This is happening on three different systems, two Windows 10 Pro. and a brand new Windows 11 Pro laptop.

Here is what I have tried to date.

On the new Windows 11 system I removed McAfee since I have a subscription to Bitdefnder. I connected the system directly to the internet on a dedicated IP connection with no router involved (a bit risky I know). Installed iCloud for Windows from the Microsoft store (version 14.2). I ensured Windows Defender was not active same with Windows firewall. Still error given above. This testing ensured there was no firewall anti-virus software blocking the connection or any possible router firewall setting causing a problem. Obviously I did not leave my new laptop in this "hacker's dream come true" state and have since installed Bitdefender and connected it to my normal home net work behind a router.

Strange thing is I know Keychain was working fine on at least one of my Windows 10 systems until recently. I am not sure when or what broke it on that system which is in daily use. Could have been either a Windows update or an iCloud for Windows update.

I have tried all other hints and tricks found after hours of research on all three systems

Disabled Proxy

Reset Network stack

Uninstalled and reinstalled iCloud for Windows (many times)

I love the ability to synchronize my passwords between my iPhone and Windows Desktop and Laptop.

Has anyone found a hidden secret salutation to this problem which Apple support should me more than aware of judging by number of people who seem to have tis same problem.

Windows

Posted on Oct 19, 2023 7:00 PM

Top-ranking reply

Apple_ICE

Level 1

13 points

Posted on Nov 4, 2023 3:25 AM

Hi RegineUser,

it looks, like i have the same problem. Login works on different devices, but fail on Windows.

The two factor window on my iPhone disapperas immeditely ... when i request an Code on the iPhone manuelly, and enter it in iCloud on Windows after approx 30 sec I get the same error.

=> Any suggestion how to fix?

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21 replies

Dec 19, 2023 12:11 PM in response to ReginaUser

Wow, am I glad I came across your post. I just recently got a new laptop and could not get past the authentication issue. So after seeing your post, I discovered my wife's iphone and ipad were listed on my devices as trusted devices. None of my devices were listed on hers however. I deleted her two devices from my iphone and like magic, I could get the icloud app/authentication to work. We are on a family plan and share purchases and our calendars. That did not stop working. However, on her two devices, under settings, it wanted her to login with my user ID and password. So, we did that and her two devices popped up on mine again as trusted devices. I immediately deleted them and now she is not getting a prompt to log in with my credentials and all is working as it should. I am no longer seeing her devices on mine nor mine on hers.

haty11

Level 1

8 points

Dec 24, 2023 9:00 PM in response to ReginaUser

Thanks Regina for sharing. This fixed it for me. Removed my wife's phone as a trusted device from my Apple ID and voila it 2FA started to work on Windows iCloud again. I have been trying to fix this issue for months. Tried Apple support but they were no help.

Jan 13, 2024 9:48 AM in response to ReginaUser

I figure out whats happening on my side ...

In my Account was an iPhone with guided access, and this leads to the immediate vanish of the 2FA code window on all iphones. After removing the iphone out of my account (thats not what I want!!), all went well.

=> Apple any idea how senseless this is?

=> Pleas fix that a code window is displayed on a device which has guided access active

Madz_3

Level 1

8 points

Jun 20, 2024 12:34 AM in response to ReginaUser

Thank you for following through this long and what I assume to have been very frustrating prosses and for eventually posting the fix for this issue. i have had the exact same issue for some time now and thanks to your efforts and kindness to share the fix i can now attempt to grow my hair back in the places where i was tearing it out. as for Apple support they should be ashamed of themselves for the lack of knowledge when contacting them regarding this issue and for not being able to resolve this issue in OS updates by now. for this reason, they can ...........

ReginaUser Author

Level 1

27 points

Jun 20, 2024 8:35 AM in response to ReginaUser

One more update on this issue.

it seem latest version of iCloud for Windows has not solved this issue.

Also from time to time when starting up my system I am required to login to iCloud which fails and I am required to remove my wife’s iPhone from my account, login into iCloud then log my wife’s iPhone back into my account to allow her access to our shared contact list and calendar.

ReginaUser Author

Level 1

27 points

Nov 9, 2023 2:19 PM in response to ReginaUser

Did you contact Apple Support?

iCloud for Windows 10/11 Keychain authentication issue