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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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Question marked as Top-ranking reply

Posted on Apr 23, 2019 7:05 PM

Thanks to mulberrywriter for the answer .

Most easiest way without downloading and deleting accounts.


  1. Go to your gmail account in browser.
  2. There is a little gear in your gmail under all emails (I did this way so explain step by step from my side)
  3. Choose Settings under that gear
  4. Choose Account and Imports
  5. Choose Other Google Account settings
  6. Choose Review your privacy settings.
  7. Choose device information. If it is Turned off - you need t click on it and turn it ON. If it is ON, You can turn it off and again turn it on.
  8. Do not logout. Go to Mail and Click on Lighting icon near your account.
  9. Click everything it will ask.
  10. In browser you will see an option to "Allow". Click it and DONE. It will finish authentication smoothly.


Process takes 2 minutes. All calendar info and emails will stay with no issues. I hope it will works fine after as well.

868 replies

Sep 23, 2019 7:37 PM in response to Ken Graham

I tried ALL THE THINGS, and no work-around has helped. I had resorted to just using Gmail and Google Calendar within Safari until Catalina came out, but when I looked up the projected release date, I found out that a public beta is available for download! I upgraded, and IT WORKS. My life can go on now. Here are the instructions I followed: https://www.techradar.com/how-to/how-to-download-and-install-macos-1015-catalina-beta-right-now

Sep 23, 2019 8:42 PM in response to lazy-ants

Looked simple, appeared to authenticate fine, but still did not re-activate the account on the MacOS mail client (or calendar)

I’ve recently upgraded to 10.14.6, and the trouble started after a password change. Internet Accounts popped up the usual box saying that it needs to open Safari to complete setup, but safari either fails to open altogether, or, if Safari has been closed and quit, it reopens to the starting (Favorites) page, with no URL - IE the redirect for the google sign-in is missing.

Turning off or on popup blocker, and restarting the Mac don’t help. Also, Apple is a jealous god - you can change the default browser, but it still insists on using Safari for adding Internet, mail, or calendar accounts.

iOS mail and calendar, on the other hand simple prompted for a password update, and carried on working.

My conclusion has to be that Apple made it worse, and that’s even taking the charitable view that they care about the problem. Sigh.

Sep 24, 2019 8:06 AM in response to amberahicks

I’m very surprised that re-installing Mojave 10.14.6 problem with Gmail was not resolved !


you might have to clear caches too and restart your computer .

Somebody is suggesting to clean chainkey, I wouldn’t recommend !

I’m pretty confidence that problem is related to Mojave 10.14.4 and after maybe some damaged files .

anyway, I had phone a phone conversation with Apple care , they collected information from my computer , either the evaluated or share it with google eng. and the result was to either reinstall Mojave or upgrade it .

My problem was that I had problem with my Gmail and to delete it from my iMac , after that I was not to set it.

when I was clicking on Google logo to add my e-mail and Password as usual and an icon used to pop up asking to « open safari « 

by clicking on « open safari » it was not going anywhere , if Mojave was installed correctly and safari / google would have opened asking to log in and then a new pop up screen asking you to allow Mac to access your gmail account and that is it !



Sep 24, 2019 9:02 AM in response to Michka12345

"by clicking on « open safari » it was not going anywhere , if Mojave was installed correctly and safari / google would have opened asking to log in and then a new pop up screen asking you to allow Mac to access your gmail account and that is it !"


That's exactly the problem, but I don't think it has anything to do with "installed properly."

According to this thread, variations of not authenticating Google Internet Accounts has been a problem since 10.14.4, but it finally bit me on a password change shortly after an upgrade to 10.14.6 and the latest Safari.

You can tell it's specific to Apple's Internet Accounts authenticating to Google, because other apps using Google SSO (to the same corporate account), such as Zoom and Slack, redirect to Safari, open a Google authentication page, and log in successfully.

On the other hand, the redirection from Mail, Calendar, Internet Accounts... either don't open Safari, or if it is closed and quit, will open a start page with no URL - IE the redirection is failing.


Out corporate IT staff tried upgrading another Mac to 10.14.6 and found they could not add/update Internet Accounts, either.

Apple acknowledged to out IT that they know of the problem and are working on it - yeah, right - only 5 months!

Sep 24, 2019 1:46 PM in response to VonLich

Appreciate the speed with which I got news about Safari 13.0.1 via this forum.

Search for updates, install, restart, and no I can add/update my corporate google mail/calendar accounts via "Internet Accounts" as it should be.


Thanks, folks


PS Apple must have made this 6 month old problem much worse in 10.14.6 to get enough blowback that they had to fix it!

Sep 25, 2019 11:57 AM in response to Ken Graham

Hey everyone. After deleting the gmail account, try shutting down your computer completely and then restarting in safe mode (power on and hold shift button until the bar underneath the apple fully loads). Add the account in Apple mail. You should be able to open in Safari at this point. After adding the account back, you should restart your computer. Mine worked! Thanks to Trevor at Apple Support!

Dec 2, 2019 4:28 PM in response to Ken Graham

So I've been having the same issue, in that one gmail account was not working on MacBook (same account worked fine on other mac desktops). I had to delete the account from Apple Mail, and then we had to delete the passwords in a few applications in my keychain (keychain access).


Once we did that, Apple Mail allowed me to re-install the gmail account without any issues. Good luck to everyone out there. If you call Apple, mention the keychain thing. They can guide you through the process.

Dec 9, 2019 2:12 AM in response to Ken Graham

What worked for me was going into Keychain Access program and deleting all the authorization tokens from Google and gmail. Do a search on the top right for "gmail" and then remove all the tokens and even the account passwords.


After that I did one more cycle on Internet Accounts and everything started working again.


For me the issue cropped up as I had to restore a backup and that included older items in the keychain Library folder, that came from my old computer.

Mojave 10.14.4 fails to Authenticate Gmail account

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