iCloud for Windows 10/11 Keychain authentication issue

Further to my fix above.

Did another test on a second Windows system and here is what I found.

With my wife's phone removed as a trusted device worked as expected but with her phone removed from my Apple ID she no longer had access to our shared calendar and contacts. Adding her access back to the shared contacts and calendar added her phone back as a trusted device on my Apple ID and broke iCloud for Windows again.

I also noticed that the notification for 2FA on my phone was again slow to appear and neither verification code from my phone or her's worked with her account added to my Apple ID. But once iCloud for Windows has been setup without her phone on my Apple ID it remains working as long as no changes to password sync are made after her phone has been added back on my account.

Hopefully this all makes sense.

BTW going to get back to support with the solution and seriously coming out of retirement and applying to Apple as a senior engineer... Lol

Think I will give Apple Support another try. Would really like to get my mail and password sync working on my new laptop.

Glad it worked. I have passed my findings on to Apple Support so they are aware of the fix. Still waiting for my checque from them… lol

I suspect the root cause was most likely due to the extra trusted device. Were you able to put the device back after your successful login to iCloud for Windows?

Sorry but that link does not address my problem at all.

As stated the issue is error message “Unable to reach Apple ID server”.

There is no problem logging into my iTunes account under the iTunes app. Only a problem when trying to use ICloud for Windows.

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.

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

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.

I reinstalled iCloud For Windows today to see if there was any change. And glory be it's now working!

Not sure if this was what was causing my problem or not but before I reinstalled I reviewed my Apple ID account and found my wife's iPhone was also registered against my account and was the first one in the list. I deleted her phone from my account.

I may be wrong but here is my theory. I know my wife was also getting my iTunes login notifications from 2FA but normally she either ignores it or dismisses it while I enter the code displayed on my iPhone. This has always worked for every thing else with no issues. But I have a feeling that for some reason iCloud for Windows was waiting for the verification code on her phone and when I entered the code from mine it failed.

Not sure why her phone was registered against my account. Only reason I can think of is I share my contacts and todo list with her. Going to have to check if this has been impacted.

I guess the only other possibility is Apple Engineers did more digging into my issue and fixed some thing at their end.