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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Posted on Mar 26, 2019 9:25 AM

UPDATE:

I contacted Apple and spoke with a tech support person, shared my screen so he could see what was happening. He verified that it is legit. Continuing with the process for each account, I was able to get my accounts online.

IF for some reason you do not get the prompt, click the sideways lightning strike (my description) next to the account that's offline, and you should then get the prompts to authenticate.

868 replies

May 18, 2019 10:04 AM in response to Ken Graham

After battling this issue for two weeks I finally spoke with a Sr. Apple advisor that could help. I have the most current OS 10.14.5. This is what we did:

Open spotlight; go to keychain application; bottom left hand side, make sure that "All items" is highlighted. In upper right hand corner "search" for any Google/Gmail related logs linked to your mail account ie: "youraccount@gmail.com". Highlight all the items related to your search and delete them. Restart Mac and retry account again. It worked for me.

Mind you, I have spent hours on the phone with other techs and this took less than 10 minutes including restart time. All has been working perfectly since.

I hope this helps. Have a great day!


This took us a total of 10 minutes including restart time.



May 20, 2019 8:57 AM in response to Everything_is_Apple

Yes, Everything_is_Apple is correct. Thanks for the tip. I no longer have gmail password loops.

It took 2 minutes. I went to Keychain application in spotlight + searched gmail + selected login + selected Passwords+ deleted only the following items:

com.apple.account.Google.oauth-expiry-date

com.apple.account.Google.oauth-token


Reactivate the online button in Mail for your gmail accounts. No need to enter passwords no need to restart. Voila!


Mar 27, 2019 6:57 AM in response to macendo

Your mileage may vary, but Macendo's updated post worked for me.


There seems to be a difference in which prompt you enter the password. Clicking on the OS notification to reenter my password for each Google account didn't make a difference - Mail still would fail for every Google account I tried. But triggering the prompt by clicking the lightening bolt icon next to the account under Inbox solved the issue for all my Google mail accounts. OSX Mail under 10.14.4 is once again working with Google Gmail accounts.

Mar 27, 2019 6:58 AM in response to Ken Graham

I had the same message this morning, but I got the google accounts registered. Here is how I did it:

  • In the "Mail" program go to "Mail/Accounts..."
  • Click on the respective Google account (if you have multiple accounts you will have to do that for each one).
  • A browser window opened. Provide your log-in information (username & password).
  • A permission page appears > Accept.
  • Instantly I got an e-mail alert, saying that I had a new sign-in.

After these steps for all of my google accounts I was able to download all of my e-mails.

Mar 27, 2019 8:07 AM in response to Ken Graham

What fixed it for me:


I had to go thru the "forgot password" routine on the Google site when Gmail authentication failed in Mail on my laptop running Mojave 10.14.4.

Changed the password on one Google Mail account after selecting "forgot password" and obtaining an authentication code from Google as a text or call (curiously the old passwords worked on two other Gmail accounts after that.)

Then, of course, had to change to the new password on my iMac and iPhone.


Mar 27, 2019 9:55 AM in response to stuuke

I tried the following workaround. It only fixes e-mail access, it is ugly, but it is working (for me at least). I

deleted my google account from the accounts list and added it back as generic IMAP account with imap.gmail.com and smtp.gmail.com as incoming and outgoing servers, respectively. No problems with authentication and my gmail account is functional gain.

Mar 27, 2019 5:23 PM in response to Ken Graham

I have the exact same issue described by everyone here: two gmail accounts, regular gmail has authenticated fine, Gsuite not, staying on an infinite loop since updating to 10.14.4. I have solved this by creating app specific password in the web settings of my google account. I know this is not ideal. because you get access only to mail and notes, but it is a temporary workaround. For me it work fine.


Mar 27, 2019 5:57 PM in response to Mirsky

I don't think any call to technicians will fix things. Nothing will fix the bug until Apple roll out an update to Mojave but there is a workaround.


There is no need to delete accounts. Just turn them off, make them inactive so you don't lose your On My Mac emails.


Then add your Google accounts using manual IMAP settings. You must also use app specific password server side on Google.


Your emails will now work whilst Apple issue a fix.

Mar 28, 2019 10:46 AM in response to Ken Graham

I had a number of Gmail accounts with this problem - although not all my Gmail accounts were affected. I got tired of waiting for a fix from Apple, so here's the workaround I used on all of them:


1) Quit out of the Mail app if it's running.

2) Completely remove (not just disable) the affected account(s) from System Preferences > Internet Accounts.

3) Log into https://accounts.google.com/signin/v2/identifier.

4) Click on Security, then click 2-Step Verification and make sure it's OFF (if you don't do this, the next step won't even be an option).

5) Set "less secure app access" ON.

6) Re-add the account(s) from System Preferences > Internet Accounts.

7) Launch the Mail app - the account(s) should sync.

Mar 28, 2019 4:43 PM in response to sueilla

AndreD's solution worked for me, as well, and I'm using a G-Suite account. The steps were slightly different, but it worked ... where nothing else did previously. My steps:


  1. Uncheck all G-Suite syncing from the Internet Accounts preference pane.
  2. Close System Preferences.
  3. Open System Preferences > Internet Accounts, and choose Calendar for syncing.
  4. Get a popup asking me to authenticate. Choices are "Cancel" and "Open Safari."
  5. I chose "Open Safari" and went through all the authentication procedures I had previously.
  6. Like magic, I'm in.


I don't know why this worked, and I don't know if all these steps are necessary. I simply (and desperately) tried to mirror AndreD's solution as closely as possible. I won't look a gift horse in the mouth, but I did want to validate that there's something here. Disclaimer, FWIW, I only sync my calendar, because our company policy doesn't allow me to use desktop clients for email. So your mileage may vary.

Mar 29, 2019 9:21 AM in response to picciano

I tried every work around posted and the ONLY one that worked for my Gsuite account was the Charles Rewrite. I had to repeat on my two Macs. Here is the process I followed. If this guy figured it out why can’t the Apple engineers fix it? https://forums.macrumors.com/threads/mac-mail-app-broken-for-some-gmail-users-in-macos-mojave-10-14-4.2175312/page-4#post-27232575

Apr 2, 2019 12:22 AM in response to Ken Graham

Finally a 100% working solution is very simple.

In safari: logout from your google suite account (to make sure you will fix the right one).

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.


The trick was simply to fix the password with the google link

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Mojave 10.14.4 fails to Authenticate Gmail account

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