If you can’t get macOS Mail to work after upgrading to two-factor authentication, here’s a way to fix it

I highly recommend Apple’s two-factor authentication (2FA) for your Apple
ID
and associated iCloud services as a way to reduce the
threat of a remote hijack of your account. (Although note that
you
can’t turn 2FA off
once you enable it.) However, depending
on how you’ve used iCloud in the past, you might run up against
a quirk: You can’t get Mail in macOS to work after upgrading to
2FA.

Apple automates the inclusion of your iCloud email account in
Mail for macOS through a few system components. If you’re
logged into your iCloud account via the iCloud preference pane,
then that pane effectively manages Mail accounts. The Internet
Accounts preference pane also lists iCloud connections along
with other accounts you’ve set up at major services like Google
and other companies for email and other services.

If you upgrade your Apple ID to 2FA, you may be called upon to
authenticate that upgrade on all your devices associated with
the same iCloud account. (You can upgrade via macOS, in which
case all the t’s are crossed and i’s dotted at that point for
authentication on that machine.) That also handles the conduit
through which Mail access iCloud for email.

But if you upgrade to 2FA and you find yourself prompted for a
password in Mail for your iCloud account, it likely means you
once set up iCloud email using manual settings, probably a few
years ago, and have just kept it that way through subsequent
upgrades. (Apple will let you create “app-specific passwords”
via its Apple ID site for third-party email, calendar,
and contact apps, but these don’t work with iCloud email.)

I have a suggestion for how to fix this, but I can’t test it,
as I have iCloud-synced mail set up correctly. Make sure you
have a current system backup with Time Machine or a clone
before proceeding.

  1. Open Mail, and choose Mail >
    Preferences.
  2. Click the Accounts button. If your iCloud account
    appears there with the iCloud logo and the label “iCloud” with
    “IMAP” underneath, and you’re still being prompted to email,
    contact
    Apple directly
    : something’s not correct with your account.
  3. If it appears as an @ icon with the name next to it, then
    your suspicions are confirmed: it’s set up like a regular email
    account. Select it and click the minus (-) button at the bottom
    of the list.
  4. When prompted to delete, confirm. This won’t delete your
    cloud-stored email, as it remains in iCloud. It will delete the
    temporarily cached copies downloaded. (If you see the error
    when you confirm deletion that “The iCloud account “account
    name” is shared by other Applications on this Mac,” contact
    Apple for tech support: something isn’t right.)
  5. Open the iCloud preference pane.
mac911 delete icloud manual account
IDG

This error indicates that there’s something else wrong with
your account.

Now we have a series of branching choices:

  • If you weren’t logged into iCloud, log in and authenticate.
    Your iCloud email should now be correctly added to Mail.
  • However, if you were already connected to iCloud on your
    Mac, look at the Mail checkbox:

    • If checked, uncheck it, respond to confirmations, and
      then check it again. This should resync the connection.
    • If not checked, click the box to check it, and this
      should sync your iCloud configuration.

If none of this solved a problem like this you have, write in
and give us details about what you’re seeing (screen captures
help), and we’ll see if we can troubleshoot further.

This Mac 911 article is in response to a question submitted
by Macworld reader David.

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