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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

Apr 4, 2019 8:46 AM in response to Joseph Masselli

>Would you be kind enough to post the procedure you used to recapture Mail 10.14.3 and utilize it. I'm totally exasperated with >trying all the "fixes" from other users, which haven't worked for me. Your procedure makes sense and I would like to try it on >my iMAC. Thanks in advance.

You have to have a backup fro MacOS 10.14.3 !

I'm using SuperDuper to make backup on an external drive.

Plug it in, an go to the applications folder on the Backup drive and copy the mail app to your desktop. Rename it to Mail Old, and then copy it to your Application folder.

Go to the Application folder and double click on Mail Old.


Apr 5, 2019 1:30 PM in response to Ken Graham

I am having the same issue where I had authenticate all my gmail emails and additionally I am having internet issues. I keep thinking my wifi is out, but it's not. Internet/WiFi stops working and I have to restart the computer. (MacBook Pro 2017). Restarting Safari does not work. And I even tried Foxfire the second this happened and that didn't work either.

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 7, 2019 10:03 AM in response to Ken Graham

I have also had a problem. Until Thursday e-mails to my gmail account were sending and receiving normally. On Friday I got a message saying "Enter the password for the account “****@gmail.com”. and a box to Open Safari. I did that, entered my password and then got a message from MacOS (Developer info 'account_support@apple.com') saying it wants to access my Google Account to 


"Read, compose, send and permanently delete all your email from Gmail


See, edit, download and permanently delete your contacts


See, edit, share and permanently delete all the calendars that you can access using Google Calendar


View and send chat messages"


At the bottom it asks me to "Make sure that you trust MacOS. I wondered if this was some kind scam but it looks as if it is an incompatibility issue.


I have the gmail app on my iPhone so am getting my gmail there and I can also pick up my gmail in Safari. The problem is that I can no longer take them out of the inbox and save them to files like I can in Apple Mail. I ma not familiar with Spark. Is this an alternative e-mail app that can be used with the MacOS?

Apr 7, 2019 12:27 PM in response to Ken Graham

I had the same issue of Mail logging out of gmail, and tried some of the suggested workarounds to no avail.

SOLUTION: What worked for me is to copy the Mail app version from my backups before the 10.14.4 update, and put in utilities folder. I launched from utilities folder and has been working ever since with no problems.

Just make sure you quit out of Mail app, and copy the app from your Time Machine backup drive (Not from the Time Machine app).

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.


Mojave 10.14.4 fails to Authenticate Gmail account

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