"Your iCloud account settings are out-of-date" notification keeps popping up on my Windows 10 PC.

This happend to me today as well. I spent all day googling on how to fix it. I wish I'd have saved the link but I stumbled upon a post somewhere that said as of today iCloud wouldn't work with microsoft calendar unless you turned on that stupid two-factor authentication. What they didn't say was about the auto generate password. Anyway 8 hours 😠 later I got it all put together and it's working again.

Amazing. I followed the instructions in your post and got it working as well. I can't believe there wasn't some notification of this requirement to use two-factor authentication in order to sync calendars and contacts on other devices (e.g. my Windows 10 PC). I have a phone call later today with Apple support, and I'm going to discuss this with them.

P.S. Thank goodness for Apple support community (specifically jcolom) and Google search (to find this thread).

Further to this for others that haven't been able to fix the problem yet, when you go to "update" your password on your Windows 10 device (i.e. Fix Account), it isn't looking for your Apple account password, as they dialog box would suggest, but rather it is looking for the device specific password that you define in the two-factor authentication process.

Crazy, but it worked. Everything I could find kept talking about 2 factor authentication... only I wasn't using it. Apparently you HAVE to be using it. I had been syncing my Windows calendar for months, and suddenly it stopped working today. Once I turned on 2 factor authorization, generated a password, and entered it in Windows... problem solved.

Thanks.

As others have reported, there is no Generate Password option in my AppleID account settings. There is only the option to set up two-factor authentication, which now BTW gives me a message:

"Upgrade available after June 19th 2017, 9:34 AM."

Seriously, Apple? You're locking me out of my email for three days? With no explanation?

Has anyone else run into this?

I've got the same problem. No generate password option. OK, so now have to create the two factor authentication? So did that - but had to re-enter my security questions too! Still getting error message in Win 10 calendar. This is a crock of sh*t...

I cannot stand the 2 factor authentication. If you have Apple TV there's some real fun for you there. I finally got the authentication in it but never want To go through that again. Anyway I hate my calendars not being synchd more. Hopefully Apple Will get an earful and change how this all works. It's the dumbest thing ever.

Once two-factor authentication is in place, go to the following web site: https://appleid.apple.com/#!&page=signin

to manage your Apple account. Use your Apple ID and password to log in, two-factor authentication will then send a code to one of your Apple devices which you'll need to enter in the dialog box. Once that is done, you'll get a page where you'll see the option to create App Specific passwords for trusted devices (e.g. your Windows 10 PC). Once you have set that password for your PC, that will be the one to enter into the Windows 10 account "fix" dialog box. That should then allow Calendar and Contacts to be synced between your the Windows 10 apps and iCloud.

Well, looks like Apple messed it up big time, one more time! Congrats, Apple! hard to deprive you of the crown of tech-bonehead, ********* software company in history. Hope you go ******* bankrupt, you jerks...

If you're not using the two-factor authentication, then you need to. Then you can generate an App-specific password. It's weird because I wasn't using the two-factor authentication and everything was working fine until a week ago. I turned on the two-factor authentication, generated an app-specific password, and voila! My windows 10 calendar and mail works with icloud! Good luck.

I have just wasted a good half hour on a spectacularly badly designed system. My only Apple product is my iPad. This has encouraged me to continue the process of migrating to non-Apple products. You know, the kind that are designed to meet my needs, not those of Apple's engineers. This is an unbelievably bad system.

iCloud just did an update, as of this post date, after which I needed to restart my PC. Still no App Specific Passwords section in my Manage Apple ID. Still got the problem. Still getting the error messages. 😟

The app specific password option should be in the Security section of the Manage Apple ID page, after you have logged in and entered the two-factor authentication code which was sent to one of your Apple devices when you logged in. Your Windows 10 PC should be listed under the Devices you are logged in to section. If all of these are in place, I'm not sure why you aren't getting the option to assign an app specific password.

I haven't tried going back. If you do, let me know how it works. 🙂

This is typical Apple nonsense. They seem to think they know what's right for us. You either do it their way, or hit the highway.

Yep. I have an iPad and an Android phone and a Windows PC. When I replace stuff, I will be moving to harmonise them. This does not encourage me to migrate towards Apple. Lovely kit, appalling attitude to customers.