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Helpful answers
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May 13, 2016 8:58 AM in response to mzeaby 63N,SOLUTION
FOR MAIL TRIGGERING THE ERROR MESSAGE: 'This mac can't connect to icloud because of a problem with <email address>'
Open Mail
Go to Preferences > Accounts
Click on iCloud account
Click on Advanced tab
Towards the bottom - make sure that it says 'Authentication: Apple Token'
I changed this, as mine wasn't set to Apple Token (previously TLS client certificate), and it has solved my problem of being repeatedly asked for my iCloud password when I open Mail.
I guess this setting gets lost when using iCloud to restore email accounts, as I had tried to do with a clean install of El Capitan.
Props to Ashton_Schmidt on the first page of this thread.
Re: This Mac can't connect to iCloud because of a problem with [email]
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May 20, 2016 5:54 AM in response to mzeaby SidRipper,The keychain fix was temporary and only worked for me until the computer went to sleep while logged out. I found the ultimate solution is to wake the machine up, then wait about 10 seconds before logging in. When I do this, the popup never appears. If I login immediately after wakeup, without waiting, the popup papers 95% of the time.
If I were to guess, there is a process that hasn't been fully spun up when the auth tries to hit the Apple servers. Waiting allows it, or all, the system services to be spun up.