"Your iCloud account settings are out-of-date" notification keeps popping up on my Windows 10 PC.

Hooray It worked!

Specifically... Log into your Apple ID from your Iphone or IPAD. Turn on Two Factor Authentication, and send out a Verification Code (6 Digits). Log into Icloud on your Windows Device. Enter the Verification Code given. Then go to manage Apple ID (on your Windows Device) and enter your verification code. Now go to Manage ID in ICloud and you will now see "generate app-specific password". You will get a password which you will then go to your ICloud account on your Windows Settings and enter that password. Whew too complicated and I'm supposed to be a techy!

Yeah, that's the solution that was proposed several times already in this thread. ???

The issue, I think, that most people are having is the fact that we are being forced to turn on 2-factor authentication to resolve this.

My recollection is that in the process of establishing two factor authentication, Apple will send a numeric code to your Apple device. You need to enter that code into your device in order to finalize the authentication process.

After that, go to iCloud and get your app-specific password, which needs to be then entered into Windows.

Convoluted enough? 😕

The issue, I think, that most people are having is the fact that we are being forced to turn on 2-factor authentication to resolve this.

Not really.

You have made a choice to use a secure Apple service with a 3rd party app that Apple has not developed. In order to maintain Apple's high level of security, to do this now, you need an app specific password which can be generated by enabling either Apple's 2 Factor Authentication or the older 2 Step Verification.

Not really.

You have made a choice to use a secure Apple service with a 3rd party app that Apple has not developed. In order to maintain Apple's high level of security, to do this now, you need an app specific password which can be generated by enabling either Apple's 2 Factor Authentication or the older 2 Step Verification.

Except I made that choice two YEARS ago, and it was only two WEEKS ago that this was required.

And the 3rd party app was developed by this fly-by-night company called Microsoft. Typical Apple high and mighty BS. If I want to be unsafe, give ME that choice. Don't make it for me.

And bread used to be 5 cents a loaf.

Things have changed in the last 2 years. You are now making a new choice then.

You have a choice. Forward your icloud mail to an address you don't need 2FA or 2SV for.

Access your mail at icloud.com

There are options, even unwanted ones. It is inevitable that all online services will require some form of 2 step protection by defailt.

Ok I’m having the same issue. 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? 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.

This option is only available if two-factor authentication is enabled successfully. I've just run into the issue where I'm put in a waiting period to enable it due to having to reset my security questions... and there's no way around it. My phone contacts are gone because of trying to troubleshoot this issue. I removed the account from my phone, hoping that it was just a bug and re-adding it would fix the issue... it did not. I didn't have two-factor auth enabled prior to this... and I don't remember being warned by Apple that this "security feature" was being rolled out. Pretty ****** off right now that I can't get my contacts back for 72 hours, and frankly based on this situation I've decided not to buy an iPhone ever.

frankly based on this situation I've decided not to buy an iPhone ever.

Adding 2SV to your Apple ID has nothing to do with owning an iPhone.

If you really want to teach Apple a lesson, stop using iCloud services like Contacts.

Ha! Reading all the way through this thread has been hilarious -- but I appreciate your suggestion that folks just get to their mail via icloud.com or by forwarding it to another account. I'm gonna do one or the other -- although disappointing not to be able to sync calendars/contacts -- because 2SV (or was it 2FA?) really messed with me a few months back on my iPhone and I DO NOT want to go through that again! I might decide later to go the other route, but I'm having enough trouble with my new Windows 10 laptop, I can't possibly deal with new Apple troubles!

So thanks, LACAllen, for the explanations -- and for your perseverance through this thread, which is quite remarkable .... 😀

I don't understand the app specific password stuff. I'm afraid to mess with my apple account and the two factor password authentication makes no sense.

I am not using two-factor authentication for my iCloud account. Do you have another suggestion for this message? Your iCloud account settings are out-of-date

I've tried to do this 100 times, but I can't see 'Generate Password' anywhere. Is there something I am missing?

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.

Are you using two-factor authentication for your iCloud account? if so, the only solution I could find that worked was to generate an App-specific password through the AppleID website (https://appleid.apple.com) and use it as the password for my Windows Mail/Calendar iCloud account.

The procedure is described in an answer by G00dbyeGirl to this Microsoft community post.