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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

Mar 29, 2019 11:32 AM in response to tboy68

Same issue by me!


Apple please stop doing updates that haven't been thoroughly tested. We, apple buyers, are paying the (big) price to have reliable hardware AND software, so do your job find a rapid solution and moreover tell your Helpdesk people to stop treating us like idiots and have an humble behaviour, and preferably a solution when problems occur.


These kind of things will drive your faithful supporters away!

Mar 29, 2019 12:57 PM in response to pedwar

Here is a thought that just occurred to me that I didn't read above: Since the problem seems to be a hang on verification through Safari, did someone try setting up or accessing their G Suite account(s) through the traditional setup (System Preferences > Internet Accounts > Google...) after resetting their default browser to something other than Safari? Like, for instance, Chrome? Can someone test this and see if it works? If it does, does it continue to work if you then set your default browser back to Safari? Maybe worth investigating...

Mar 29, 2019 1:06 PM in response to Mirsky

This did work for me but it took me a second try to get it done correctly. I am very grateful that Mail, Calendar, Notes, and Contacts are working correctly. The Gmail web interface really sucks. Searching doesn't seem to work which is odd for a search company, it is difficult to have 2 or 3 email open at the same time. This is just a unfortunate glitch that Apple really needs to be public about--GET OUT IN FRONT OF THIS....oh wait. Too late for that!!

Mar 29, 2019 3:09 PM in response to ervin208

ervin, AirPods were released in late 2016, well after Steve Jobs passed away. No new products? HomePod. iMac Pro. AirPods. Various services and such. Jobs died in 2011… not a year ago.


Nobody wants a bug fix that makes anything worse. You can still get your gmail - just log in to the web site - so a little patience for a good fix is not unreasonable.


Unlike your comment, which I find most unreasonable.

Mar 29, 2019 4:00 PM in response to Ken Graham

Been trying to fix this problem for me for several hours now. I've done absolutely everything that has been suggested in the replies. Although, after a little bit of research and digging, it looks like those with 10.14.4 update already installed are experiencing a bug in the software update that didn't get fixed while it was still in beta, and that there isn't really any way around it other than when they fix it in the next update. Hopefully it'll get addressed soon, as it makes accessing my mail extremely inconvenient.

Mar 29, 2019 7:19 PM in response to iacas

Maybe it was something else during the procedure or a different issue with your accounts.

I have multiple reports stating the "Charles"procedure works for all people that tried it.


Personally, I had previously removed all certificates pertaining to the affected accounts (Keychain app) and rebooted my system. You should try the same and double-check if the Charles procedure was performed exactly as I posted.

Mar 29, 2019 7:20 PM in response to ym11

It doesn't work for "all" people. Others have reported that the Charles trick has not worked for them. I followed the directions as written.


I've not deleted any accounts or done other things that some have indicated screw things up more than they help. I'm not terribly interested in trying to delete certificates or other things as of yet. It's not quite that important yet for me.

Mar 29, 2019 8:12 PM in response to API1Cat

Just re-tried two different accounts (GSuite, named domains under old free 'plan') on two different laptops just by clicking on the 'lighting bolt' icon next to the accounts in the LHS mail.app pane, entered details into the Safari pop-up window and all good on both accounts.


Likely a Google server side fix. (Assuming the accounts keep working.)

Mojave 10.14.4 fails to Authenticate Gmail account

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