Eli Sherer wrote:
Last week I traveled out of the country (Turks & Caicos) and when I logged in to Windows 10 (in Bootcamp), iCloud asked for my login password. I thought nothing of it until I got home.
Now, iCloud in Windows asks for my password every 10-15 minutes, which of course must be approved by entering the two-factor code from my phone. I have entered the password and code at least two dozen times in the past couple of days, and it always asks again later.
I have tried deleting iCloud, reinstalling, and rebooting the machine between every action. I noticed that my iCloud drive folder is also empty after the last reinstallation process.
To say this is frustrating is an understatement. I only use iCloud in Windows for synchronizing bookmarks (Chrome and Internet Explorer), and for the iCoud Drive. But both of these are necessary for my work.
Any ideas are quite welcome. Apple says that because it's a Windows thing, they give up!
Found this response in another discussion here, and it worked for me. https://discussions.apple.com/thread/8061821
A recent update has made app-specific passwords necessary in order to utilize your iCloud email account with non-Apple devices. This means that, in order to sign into Outlook with your iCloud email account, you need to set up an app-specific password, as detailed here: Using app-specific passwords - Apple Support. In order to use an app-specific password, you first need to set up two-factor authentication, as detailed in this article: Two-factor authentication for Apple ID - Apple Support.
Once you've done that, you can add your iCloud email account to Outlook, using the steps here: iCloud: Set up iCloud Mail on your devices.
I already had 2-factor authentication turned on, so all I had to do was sign into appleid.apple.com and generate an "app specific password" in the security section below the list of my trusted hone numbers. I then used my iCloud email and the new password, and have iCloud in my Mail, Calendars and People apps.
I hate Outlook and when I used the iCloud app for Win 10 it started to use Outlook in Office 365 for syncing my data instead. I prefer the simple apps myself.