Mojave 10.14.4 fails to Authenticate Gmail account

Just update to Mojave 10.14.4 and now Apple Mail will NOT connect to one of my Gmail accounts.


This issue is UNIQUE to Apple Mail as I can access the Gmail account using Spark on the same computer without issues.


This issue is UNIQUE to Mojave 10.14.4 as it did not exist with 10.14.3 and it does not exist on another computer running an earlier version of Mac OS X.


The issue puts me in an endless loop. I get a notification "Google requires completing authentication in Safari." This takes me to a Sign in dialog where I enter email account and password. Password is correct and accepted, after which I'm back in the loop again asking to enter Google Password.


If I login to my Google account in Safari I can see the recent events that I signed in without any problems on this Mac, but Apple Mail does NOT connect and I am back in the endless loop.


Oddly I can add events to the Google Calendar for the account so apparently something is amiss strictly with Apple Mail.


Suggestions?

iMac 27" 5K, macOS 10.14

Posted on Mar 26, 2019 8:18 AM

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Posted on Dec 27, 2019 11:41 AM

This worked for me on 8 different Gmail accounts. The glitch happened last night 26Dec19 when I installed a Mojave upgrade.

Note: I am running Mojave 10.14.6, Safari 12.1.2, and Mail 12.4 which may be why it was this simple.


  1. In "Mail," click on the tilde next to the account now connecting. It will pop up a box saying, "Enter the password for the account “**************@gmail.com”. Click on "Open Safari"
  2. Now you see "Sign in to continue to Mac OS." Don't - It's a loop. Instead click on "Create Account" at the bottom.
  3. Don't create a new account. Look below (lower left) and click on "Sign in Instead." It will reopen a log-in box for your Google account.

4. Log in to Google with your email and password (two pop up boxes in a row).

5. It will pop up Google’s "Protect your account." Click on "Confirm"

6. New pop up window, "macOS wants to access your Google Account." Click on "Allow."


Your “Mail” screen will pop to the front and the tilde will be gone. Your mail will now function. Do a test and it should come through.


For those using the same specs as my Mac, hope this works for you also. Since I had 8 accounts to fix, it seems true (but it was one laptop with particular specs). I actually stumbled upon trying this before any solution offered - God's grace maybe. If it works for you, send Him a "thanks."


Merry Christmas!

868 replies

Apr 7, 2019 1:56 PM in response to Ken Graham

Since update to 10.14.4 iTunes Match fails to update iCloud Music Library too! Including the issue referenced in this thread. I’m adding to the thread about update fails. I don’t feel like starting another thread about iTunes Match. Also, I’m not looking for answers.


Apple Support confirmed they know about the issues and a “Fix” is being finalized.


Mar 26, 2019 12:07 PM in response to stuuke


This happens because when you log in you receive a token and a refresh token. The token is only valid for a brief period of time (something between 12 and 24 hours). Then it is not valid anymore and you need another one.


The OS then goes to Google with the refresh token, and then Google gives you a new pair of token and refresh token, and the operation proceeds.


What happened is probably related to how this token handled and/or stored, which basically means our tokens expired, iOS/macOS tried to refresh it, and the problem happened, requiring us to log in again. And the bug is on the token so no matter what we try, Google refuses the token forever.


This is the same process that happens when you change your password, and allows you to be authenticated for a good period of time while still allowing you to invalidate other log in sessions.

Mar 27, 2019 5:10 AM in response to Ken Graham

Same problem. Writing to save people time who might be trying to fix this or find a workaround. I have been in phone contact with Apple upper level tech support. Since updating to 10.14.4 I cannot connect to Gmail (I can access iCloud mail) using the native Mac email client though I can access Gmail using the Thunderbird email client on my Mac. I can access Gmail on my iPad and iPhone.

Here is what upper level Apple Tech suggested. I tried everything. Nothing helped. They offered to revert me to 10.14.3


Deleted the Gmail account and reinstalled.


Reset my SMC and my Pram.


Set up a new administrative account and tried to access Gmail on that account using the native Mac email client.


Reinstalled MacOs 10.14.4


Again, none of this helped. I filed a bug report. If others did the same it might get Apple's attention sooner.



Mar 27, 2019 9:04 AM in response to observer_144

Both of my gmail accounts are pretty old. The GSuite one doesn't work even after changing the password. The regular Gmail one is, knock on wood, still functioning.


At least in changing the password I got the prompt to "allow" Google to do certain things, but it still doesn't work after that.


I don't think there's any difference between the lightning bold and the "Login Failed" link. Both fail here.

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Mojave 10.14.4 fails to Authenticate Gmail account

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