Or they’ll enter the password, it’ll seem to accept it, but then it’ll pop up the same dialog box again in five minutes or after a reboot. They’re seeing something like this:Īnd if they click “iCloud Preferences” on that box, it’ll take them to a place where they get stuck in a never-ending loop of typing in the right password. I’ve run across a recurring problem with clients in which older devices will ask for iCloud passwords over and over again, and the prompts won’t stop coming despite the user entering the correct one multiple times.