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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

Jul 1, 2019 1:32 PM in response to Ken Graham

I have the answer... here is what I did and got it to work.


1.- remove the keys and certificates from the keystore (under Launchpad/Other/KeyChain Access), search for google and remove them all


2.- remove the two step verification with my cellphone... (Google Security under accounts) not sure if needed, but i wanted it to be straight forward


3.- Removed the Google account under the (System Preferences/Internet Account) on the Mac


4.- Removed access to MacOS (Google account/Security/Third-party apps with account access)


5.- Reboot, just to be clean...


6.- go to System Preferences/Internet Account/ add google account.


That seemed to have worked for me after sooooooo many weeks of trying, i am in..!


please let me know if this helps you.

Jul 4, 2019 6:42 PM in response to markfrompalmyra

Ok, this is what worked for me.. once I added google under the Internet Account (System Preferences/Internet Account), the Google Account Mail should be in the list of accounts of MAIL, but is disable or fade out, all you have to do is selected and there will be an option to "Enable This Account"


but you must add the Internet Account, at least that is how it worked for me.


Thanks, hope that helps.

WDM

Jul 8, 2019 7:55 AM in response to maggieb5x

I have wrestled with this problem since 26 March, the day I upgraded my system to 10.14.4. Apple didn't fix it in the next upgrade either. The workaround I am using, which was published in this forum weeks ago is: deactivate (not delete) the gmail account that is affected. proceed through the steps to establish a new gmail account. In my case the new account works just like the old one did before the authentication problem began. I suggested not deleting the old gmail account just in case, some day, Apple does its job and gives us a fix. At that time, we can decide whether to continue with the newly established account or apply the fix to the old gmail account and use it as before. Good luck!

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 11, 2019 2:38 PM in response to Ken Graham

Hello, I had the same problem


I could solve it in a few steps:


Open Mail-App on e.g. mac-mini

Goto Mail/accounts

Select the Gmail-account

--> Delete the toggle in mail

( I'm not sure if i then temporary closed the mail app )

--> Activate the toggle in mail


And then everything was ok, no more

"endless loop. I get a notification "Google requires completing authentication in Safari."


Jul 12, 2019 11:14 AM in response to Jedesache

Jedesache wrote:

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.

There are discussions around about the SOCKS Proxy enabling itself after every restart. It was tracked down to probable malware on the affected machine. Using the free version of MalwareBytes the malware was removed and the issue was resolved. I would urge any here with the authentication problem to check the status of their Network preference panel to see if the SOCKS Proxy is enabled. System Preferences->Network->Advanced->Proxies. If it is, turn it off and download the MalwareBytes app to check your system for malware. Now check if the authentication problem still exists.

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.

Jul 31, 2019 12:19 PM in response to Ken Graham

I had this exact problem. Called Apple Support after not finding a solution here. Many things were checked and postulated but in the end they suggested I boot in Safe boot. This "repaired the directory" and fixed the problem. I'm not exactly sure how that fixes this, but it did. Try Safe boot and sign in again. The Google authentication works and then exit safe boot. Still working.

Sep 23, 2019 12:17 PM in response to PetrasKazis

It is due to not complete Mojave 10.14.4 / 6 installation !

1- Reinstall Mojave

2- System Preferences / internet Accounts/ Click on Goole logo / open safari

It will open safari asking to login to Google account and then the a google request pops asking you to allow Mac OS access you account.

By allowing Mac access your google account authomaticaly gmail will installed on your iMac/ MacBook

Just make sure that Mojave has been installed correctly on your Mac.


good luck,


Mojave 10.14.4 fails to Authenticate Gmail account

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