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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 25, 2019 8:08 PM in response to Ken Graham

Spent FOUR HOURS on chat and phone with Apple today. The first three were bullshit from Apple where they wouldn't admit there was a problem, let alone that they had even heard about it. In which case a) their front-line CS personnel aren't properly trained, or b) they're lying. This isn't a good look for Apple. I pay thousands more for their products because I expect them to work, and for them to fix the problem if they don't. Amazon and Google are SO FAR AHEAD of Apple, which is tragic, because it used to be the reverse. With Apple's crumbling ecosystem (Amazon and Google crush them in home automation, gmail, online shipping, online original video content, and their hardware now becoming not worth the 3-5x asking price, I fear they are on the way out.


Anyway, after all this time, I got to someone who said, "Oh, yeah, that problem, let's try this fix." From there it took 10 minutes and things were resolved. You have to delete any keychain data that contains google or gmail, basically. Contact Apple and insist that you know there's a problem, send them this screenshot if they deny it. Their first-level CS support seems to be trained to obfuscate and deny. Immediately ask to be transferred to a supervisor.

Apr 26, 2019 9:06 AM in response to Ajax8161

I'm following your lead and want to fix this problem. Before I proceed with the keychain deletions, can you tell me what happens when I delete them?


Also, I'm in Rome, Italy and suffered through over an hour with Apple Assistance in Italy. They took the same position of ignorance of the problem. My assistance request number is 2000045928566. I contend Apple is Apple and at least here in Italy they are aware of the problem. Following the exhaustive dialogue, screenshot, etc., we closed the discussion because Apple needed to study for a solution. I was told to call back, citing my number above and ask for the status. I decided to start using Spark instead, I don't have time for these relentless, time-consuming chit-chats. Hope to hear from you.

Apr 26, 2019 10:13 AM in response to IrwinGJr

Just got off the phone with first line Apple support. They now are aware of this problem and the fix appears to work. Unfortunately I did not record the instructions or write them down step by step. Basically the fix involves deleting google related id tokens and oath's in keychain, deleting the google account, restarting and re-adding the google account. Wish I could be more specific.

Best part was that I got a call back immediately and did not have to spend hours waiting. Hopefully they will put out an OS update soon to fix this problem.

Apr 26, 2019 2:14 PM in response to mulberrywriter

Well, it appears now that I'm in the same boat as you. Every fix fails after a while and then doesn't work again. I'm so frustrated by the wasted time. I'll try this 1 more time with Apple support but after that I'm getting rid of Mail. I'm having simultaneous issues with iCloud sign-in, works fine and when Gmail accounts go to ****, usually iCloud goes along with it.

Apr 26, 2019 2:34 PM in response to IrwinGJr

Thanks! I'm just on the phone with Apple (same as you, has been very fast response from them thankfully). I was given the same fix yesterday as you and it worked...until today! My accounts weren't working for the last 5 hours but now seem to have come back up again. I cannot send from them though, smtp server is off-line and try as I might I cannot get them back without ending in that same endless authentication loop. It sounds like I'll be passed onto someone more senior, just on hold right now.

Apr 27, 2019 12:33 AM in response to aulicanada

This works for me !

Go to https://accounts.google.com/DisplayUnlockCaptcha to repair the access (documented on https://support.google.com/accounts/answer/2461835?hl=en)

after fixing add the account in the mac os settings or over the mail app as usually (you don't even need to delete it first if it's already added).

After verification in the opened safari window everything will go well.

Apr 27, 2019 2:49 PM in response to Joseph Masselli

This is the best I can reconstruct what the Apple tech instructed me to do. Refer to my post from yesterday. In Keychain, search "com.apple.account.google" under all items and then delete all results. Then delete your google account, restart, and then add the account back in. This has worked so far with a minor bug, as it appears that the email app lost connection to google when the computer slept overnight, but was able to reconnect when told to get mail.

Mojave 10.14.4 fails to Authenticate Gmail account

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