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 13, 2019 7:54 AM in response to gjdkeu

The error doesn't occur if you setup a new user account. Works just fine with authenticating and setting up the same account. So there's something associated with the user library folder and authentication. A certificate... something. My next test is to delete all internet accounts, destroy and create a new keychain for the user. Go in to the ~Library/Mail folder and destroy all leftover folders from those deleted email accounts. Then I'll try again.


if that doesn't work... i'll just migrate all the user data to a new user minus the ~library folder.



Apr 25, 2019 8:08 PM in response to Ken Graham

Spent FOUR HOURS on chat and phone with Apple today. The first three were ******** from Apple where they wouldn't admit there was a problem, let alone that they had even heard about it. In which case a) their front-line CS personnel aren't properly trained, or b) they're lying. This isn't a good look for Apple. I pay thousands more for their products because I expect them to work, and for them to fix the problem if they don't. Amazon and Google are SO FAR AHEAD of Apple, which is tragic, because it used to be the reverse. With Apple's crumbling ecosystem (Amazon and Google crush them in home automation, gmail, online shipping, online original video content, and their hardware now becoming not worth the 3-5x asking price, I fear they are on the way out.


Anyway, after all this time, I got to someone who said, "Oh, yeah, that problem, let's try this fix." From there it took 10 minutes and things were resolved. You have to delete any keychain data that contains google or gmail, basically. Contact Apple and insist that you know there's a problem, send them this screenshot if they deny it. Their first-level CS support seems to be trained to obfuscate and deny. Immediately ask to be transferred to a supervisor.

Apr 26, 2019 10:13 AM in response to IrwinGJr

Just got off the phone with first line Apple support. They now are aware of this problem and the fix appears to work. Unfortunately I did not record the instructions or write them down step by step. Basically the fix involves deleting google related id tokens and oath's in keychain, deleting the google account, restarting and re-adding the google account. Wish I could be more specific.

Best part was that I got a call back immediately and did not have to spend hours waiting. Hopefully they will put out an OS update soon to fix this problem.

Apr 27, 2019 2:49 PM in response to Joseph Masselli

This is the best I can reconstruct what the Apple tech instructed me to do. Refer to my post from yesterday. In Keychain, search "com.apple.account.google" under all items and then delete all results. Then delete your google account, restart, and then add the account back in. This has worked so far with a minor bug, as it appears that the email app lost connection to google when the computer slept overnight, but was able to reconnect when told to get mail.

Jul 10, 2019 3:37 PM in response to GIOSMITH

This is the ONLY thing that fixed it for me! But this issue was with a q.com email address that was failing to authenticate. As soon as I disabled SOCKS Proxy and went to Mail to add the q.com email account it added instantly. This Mac was running 10.14.6. On another Mac running 10.14.3 SOCKS Proxy was NOT enabled and it has always been able to add the same account right away.

Jul 20, 2019 7:27 AM in response to Ken Graham

I tried all of the solutions listed and still nothing helped. But one simple thing did that took me an hour to figure out.

I tried to add the google account, it brought up the text box saying safari will open to verify the internet account (for a university email), Safari opens a private browsing window, I type in my gmail information, and then the page loads saying "Safari cannot open the page" and a long html text reason appears on the whole page. I right clicked on my trackpad and hit the option that said "Reload page" and then everything worked. Something so simple, but just wanted to add my two cents in case people were still having an issue and wanted something else to try. This was done after exhausting all of the other solutions mentioned here so if this doesn't work right off the bat, it may be a combination of some or all others.

Mar 27, 2019 2:42 PM in response to Youxin

After 2+ hours on the phone with senior Apple tech, here’s a work-around that worked for me:


1. Open Keychain and search for gmail


2. Delete any entries related to your failed email address


3. Search for Google


4. Delete any entries related to your failed email account


5. Close Keychain and Apple mail if it is open and restart your machine


6. Go to System Preferences, Internet Accounts and delete your failed email account (-)


7. Add a new account (+) only do NOT select Google, choose Add Other Account, then @ Mail Account


8. Enter your name, email address of your Gmail account, and the password for your Gmail account


9. For incoming Hostname enter map.gmail.com, for Outgoing Server enter smtp.gmail.com


10. That should generate a proper account in your accounts list


11. Close preferences, rsetart again and open Mail



Hopefully that solves your problem, it did mine.


Longer term will require a fix by Apple





On Mar 27, 2019, at 2:13 PM, Apple Support Communities <discussions-updates@email.apple.com> wrote:

Apple Support CommunitiesScott Willsey has posted in the macOS Mojave community.Mojave 10.14.4 fails to Authenticate Gmail accountIt's perfectly valid to be frustrated about this issue, but this has NOTHING TO DO with whether or not Apple is making tv shows. Those two Sony guys? They don't know how to write email clients or handle oauth or do anything related to email other than fire one off to Reese Witherspoon and Big Bird to see if they're available for a project or two.

Apple has always had bugs in their software, like everyone else, and they always will. My first personally owned computer was a 128k Mac way back in 1984. I can attest that every Mac OS version and every Apple application has had bugs and issues.
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