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

Mar 28, 2019 6:37 AM in response to Ken Graham

Same here. Getting "Enter the password for the account (null)" when adding a G Suite account an a clear installation of a recent Mojave or getting a notification that account has been already added and showing the name of the regular gmail account that has been added and then removed before.


What's even more bizarre and made me really puzzled is, when I created a new user account (non admin), restarted, logged into the new account and tried adding a G Suite account (without setting up icloud or doing anything else) it tried to add that G Suite account, failed and displayed the name of my regular gmail account which was never entered on that brand new user account! How can it even be possible to get the name of my regular gmail address in that new account? For me looks like a potential security issue.


The workaround has already been mentioned: "Add Other Account" and add smpt/imap info manually. For that you might need either creating a password (when using 2-factor authentication) or allow "Less secure app access" in Google Account Security settings. Doesn't look as nice as a google account (i.e. "All mail" mailbox of a G Suite account isn't included in the global "All mail" mailbox, calendar or contacts isn't connected), but at least email works.


I'm extremely disappointed: first with getting serious unrecoverable hardware errors with my SSD after only like 16 months of usage of a macbook pro, and now getting such software errors which are hard to figure out unless using some Google Fu and landing on this helpful thread.

Mar 29, 2019 11:01 AM in response to Mirsky

The direct link for the Charles rewrite is here from MacRumors user @Gannett. Follow the instructions carefully. Charles is a free download, runs for 30 days, and has a 30 minute timeout – some of us should buy or donate to thank him!


As best I can tell this process need only to be performed once per account to verify. Charles does not need to be running after that.


Also note that you need to repeat this process one by one for each G-Suite account by updating the email address in step 9 and then accessing the account in Apple Mail "Accounts". I had to select Contacts or Calendar and then click on another Account to trigger the Safari update window. 


Good luck ... YMMV



Mar 29, 2019 11:15 AM in response to Ken Graham

Hey all,


This happened with my university account too. The way I fixed it was to delete the account completely, retart, and then add it all over again. This should set it back up as a new account, completely ignoring any previous account.


Do this in system preferences and disable mail in this final setup section. Restart, then manually re-enable the mail. Hopefully this workaround might your accounts!


Mar 29, 2019 11:15 AM in response to Ken Graham

tl;dr Apple is aware of the G-Suite Gmail authentication problem and is working it but does not yet have a solution that works for everyone. 


I’ve had two phone sessions with a Mac Senior Advisor at Apple to help resolve my G-Suite Gmail authentication problem. Yesterday, after several attempts to resolve the issue that didn’t work, he went to the Engineering team to get advice on next steps and called me back today. Based on feedback from Engineering, he had me remove all of the keychain entries associated with my Gmail accounts then try authenticating my G-Suite Gmail account. Still didn’t work, same endless authentication loop. He confirmed that Apple has been getting many reports of this problem and is working it, but removing the Gmail keychain entries has worked for some people. He also confirmed most of the authentication issues are with G-Suite accounts, but not all. My guess is that some people who have a Gmail account and report the problem don’t know if it’s managed through G-Suite. The advisor said he would either get back to me with a proposed fix/work-around, if Engineering is able to come tip with one, or it will come out with the next Mojave update. So this may be awhile before it’s fixed. I will post any feedback I may get from the advisor.

Mar 30, 2019 2:03 PM in response to loopless

Sorry, the problem has NOT been "fixed".


My WORKAROUND was to delete and recreate the accounts (currently waiting for a few 100k mail items to synch...) but my accounts now display an alias (WRONG) email address (account name for Google) in the account details. I had to manually correct this email address in Mail preferences.


Yes it works... but not correctly



Apr 7, 2019 9:48 AM in response to Ken Graham

I've had this problem, none of my email accounts would connect at all. I also noticed that Safari had changed to using Yahoo as a search engine despite the preferences still being set to Google. Looking around I found that in the <Advanced Settings> in Safari preferences the SOOCKS proxy was turned on. As soon as I turned it off all my emails downloaded and my search engine seems to be back to Google.

Apr 13, 2019 7:52 AM in response to Ken Graham

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.

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Mojave 10.14.4 fails to Authenticate Gmail account

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