Q: Mavericks asks for icloud password everytime on startup

I had same problem,

In the keychain more than one login created(cached), I erased one of them and it solved my problem.

It doesn't seem like we are all dealing with the same issue here because some people it have fixed the problems others seem nothing fixed the problem. I am one of those in the nothing works camp.

Here is my issue in detail.

Every time i boot up i get the icloud password dialog. Entering the correct password doesn't work. The dialog will just pop right up again like you didn't have the correct password. The only way to get rid of the dialog is to click the cancel button twice. It will not display again until you reboot.

Second annoyance: I started getting a icloud password dialog from fantastical

What i did to "try" to fix it (nothing worked):

Signed out of icloud in settings and resigned in.

I had applecare+ so i decided to give apple a call. So far they have not been able to figure it out. Started with 1st level support and they then set me to Senior support (2nd level). They have had my create a new account (which tells you its a computer problem and not a specific problem with the account i logged in under), dump my keychange and recreated it, take off 2nd factor auth. They had to send the issue at this point to engineering. So i'm waiting for engineering at this point to investigate my account.

I have mac OSX 10.9.5 in a 13 rMBP.

Whats wierd is this just started happing out of the blue. I hadn't applied any types of updates.

This is happening to me too. Just started suddenly a few days ago. I am getting two consecutive zombie login dialogs after rebooting, when I am already logged in to iCoud.

YAAY ITS FIXED! It turns out iMessage was not logged into iCloud with a 2FA generated “Application specific password". Sheesh!

That is especially stupid since I have not run iMessage for at least 3 months and never even knew about such a maximum-security password, and iMessage is shown nowhere on the iCloud Prefpanel.

Gargantuan fail, Apple.

I'm curious if anyone experiencing this issue had a me.com email address that they originally signed up with as their iCloud or .mac account?

I'm experiencing very similar issues currently with iCloud keychain.  I had a very difficult time signing out of iCloud at all.  Apple Tech Support helped me get signed out of iCloud after a couple hours of troubleshooting, but even after getting signed out and signing back in, I still can't authorize with a code or through another device.

After signing out, I noticed that my me.com address which I used as my original iCloud userid was auto-populating in the iCloud preference pane.  Thought that was odd and might help track the issue back to it's actual problem, if so.

Thank you DianeofOregon!

Yes, that was the solution for me (finally).  You would think the dialog window would ask for an app specific password as a clue.

I had this malady on my iMac.  There is no apparrent way to determine what process is creating the popup.  Other messages hinted that one source might be the Messages.app that Apple has been working into various iCloud and iOS functions.  I opened Messages, and opened its Preferences pane.  In the Accounts tab, my old userid@me.com address was grayed out.  This (now) secondary iCloud account was the culprit.  When I tried to update the password, Messages FINALLY told me I needed an "app-specific" password, which I had to obtain through https://appleid.apple.com/?localang=en_US using my primary Apple ID.  When I got the app-specific password for "Messages and FaceTime" , that satisfied the prompt.  My actual AppleID password was useless.

This wasted a great deal of time, trying to track this glitch down.  Very poor information provided by Apple programmers.

The iCloud password pop ups started occurring for me out of the blue on startup. Settings > iCloud > Sign Out of account, then signing back in, resolved it for me.

I get the same password window, I don't use iCloud or FaceTime or any other cloud based system from Apple, how can I get it to stop asking? Total wast of time

Perhaps  you  do use Search my  Mac?

If the answaer is Yes, try this: System preferences  >>  iCloud  >>  remove the tick at Searcht my Mac and/or uncheck  everything; then Log out from iCloud. This solved my problem.

Yes, this helped me too! I hardly ever use iMessage on my Mac, but never having set a secondary app specific password for iMessage caused this behavior. Also very annoying that the pop-up window did not specify why it asked for a password. If they'd just explained that from now on one should use app specific passwords and that's the reason that you have to log in again... But oh well, it's fixed now.

Thank you, Diane, for the iCloud password/keychain access fix. You seem trés professional. Makes sense your a five.

John the Poet, Manhattan, New York. If you're inclined: prisonerofrhyme.com. Bon chance!

This is still happening after I thought it was fixed. Does anyone know a solution? I am getting tired of dismissing duplicate login windows after every reboot.

I just entered the password right there at the prompt and they stop coming back again. The strange thing is this iCloud popups only happens on my Mac Mini at home but not on my Mac Pro at work.