"Your iCloud account settings are out-of-date" notification keeps popping up on my Windows 10 PC.

Using app-specific passwords

App-specific passwords allow you to sign in to your account securely when you use third-party apps with your Apple ID.

App-specific passwords are single-use passwords for your Apple ID that let you sign in to your account and securely access the information you store in iCloud from a third-party app. For example, use app-specific passwords with Microsoft Outlook, Mozilla Thunderbird, or other mail, contacts, and calendar services not provided by Apple. App-specific passwords maintain a high level of security and help ensure your Apple ID password won’t be collected or stored by any third-party apps you use.

To generate and use app-specific passwords, your Apple ID must be protected with two-factor authentication.

If you don’t have devices that can be updated to iOS 9 or OS X El Capitan, you can set up two-step verification and generate app-specific passwords.

Generate an app-specific password

1. Sign in to your Apple ID account page.
2. In the Security section, click Generate Password below App-Specific Passwords.
3. Follow the steps on your screen.

After you generate your app-specific password, enter or paste it into the password field of the app as you would normally.

Manage app-specific passwords

You can have up to 25 active app-specific passwords at any given time. If you need to, you can revoke passwords individually or all at once.

1. Sign in to your Apple ID account page.
2. In the Security section, click Edit.
3. In the App Specific Passwords section, click View History.
4. Click next to a password you want to delete, or Revoke All.

After you revoke a password, the app using that password will be signed out of your account until you generate a new password and sign in again.

Any time you change or reset your primary Apple ID password, all of your app-specific passwords are revoked automatically to protect the security of your account. You'll need to generate new app-specific passwords for any apps that you want to continue using.

This change was made almost 2 months ago and details are available via dozens if not 100s of conversations here and elsewhere.

The delay is likely due to you making other changes to your Apple ID just prior to asking for 2SV.

Two-step verification for Apple ID - Apple Support

Feedback for Apple goes here >>> http://www.apple.com/feedback/

Please read the previous posts.

And I was always able to retrieve my iCloud mail for 2 years using this computer from Win 8 to 10. My mail just stopped working last month July. I have a regular account that’s not Two Factor Authentication. Why can’t I sign in now? Or is it forcing me to setup Two Factor on the account?

As of June 15th, all 3rd party apps needing iCloud access must use an app specific password.

Using app-specific passwords - Apple Support

Which needs either Apple's 2 Step Verification or 2 Factor Authentication enabled on the Apple ID.

I don’t want to use that feature if that’s the case and it’s not fair iif I’m being forced to add it.

Feedback for Apple goes here >>> http://www.apple.com/feedback/

I just finished an extensive chat session with a Microsoft technician, and the conclusion was that it wasn't a problem with the Microsoft server or Windows 10, but appears to be something on the Apple iCloud server side.

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.