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

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1 reply
Question marked as Helpful

Nov 4, 2023 3:25 AM in response to ReginaUser

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?

8 replies

Oct 20, 2023 2:15 PM in response to ReginaUser

Hello ReginaUser,



Thanks for that info and for choosing the Apple Support Communities. If we understand correctly, you are unable to log into iCloud for Windows on multiple computers, as you get an error message. To help with this, please follow the steps in this Apple resource If you can't connect or sign in to iCloud - Apple Support and then contact Apple directly if you need further assistance:



Apple Support



Cheers!

Oct 22, 2023 10:01 PM in response to ReginaUser

Further to my information above and after spending considerable time on the phone with support I have discovered the following


I used a spare iPhone 7 to create a new Apple ID.


Testing with this new Apple ID worked as expected in all instances on two of the three systems which previously failed to connect to the Apple ID authentication server. This was tested on a desktop system hardwired to my network and my laptop over my usual WiFi. Both my antivirus and firewall (Bitdefender) were turned on and working. On both the laptop and desktop both a newly created account and my existing Windows account were used for testing and both worked as expected with the newly created Apple ID but both failed with my existing Apple ID.


From the above tests I can only come to the conclusion the problem is with my Apple ID and has nothing to do with my Windows systems of home network /WiFi.

Question marked as Helpful

Nov 4, 2023 3:25 AM in response to ReginaUser

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?

Nov 4, 2023 12:07 PM in response to Apple_ICE

Have you tried creating a new Apple ID? Try that and see if it works. In my case a new Apple ID worked as expected. Obviously this only works for testing and switching to a new Apple ID is not practical as it would involve resetting all your devices and access to all iCloud content and subscriptions would be lost.


as mentioned in my original post the problem is definitely connected to our Apple ID and there is nothing we can fix.


Contact Apple support and insist your problem be escalated. Do not let them do what they did to me and spend hours on the phone going through your network settings. If it was a problem with my network or system a newly created Apple. ID would suffer the same fate.


good luck

Nov 5, 2023 9:30 AM in response to ReginaUser

No, cause the 2FA Login with iTunes installed on the same PC works well. So this seems to be an problem with the iCloud App update on Windows. It worked before fore a really long time without any trouble.


Yes, the Apple support ist sometime say a littel bit "simple" in really understanding the problem. My experience is they not really understand thier products ...

Nov 5, 2023 9:43 AM in response to Apple_ICE

Yes agree it worked previously.


But my gut feeling is the update caused a problem with my Apple ID which is why a newly created Apple ID works flawlessly.


Last I heard from support was they are working on an update to the iCloud for Windows app but no date available. In my opinion that answer is just a delaying tactic while they try to figure out the true root cause and how to fix our issue.

iCloud for Windows 10/11 Keychain authentication issue

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