Mojave 10.14.4 fails to Authenticate Gmail account

In my MacBook Pro 2018 10.14.5 didn't solved.

I solved deleting my gmail account and adding a new account NOT using gmail preset, but using Other Account in System Preferences, Account. Then I unchecked everything but the mail flag.

JB-SF wrote:

I have two gmail accounts using 10.14.4 One account logs in all the time. The second account goes through the endless relogin loop. Maybe someday Apple and Google will get their act together.

Update to Mojave 10.14.5 and see if it’s better.

The DisplayUnlockCaptcha solution does not work for me. I have had this same issue since updating to Mojave a month ago. I cannot get one of my gmail accounts back into Mac Mail and so have to do all those emails in the browser and have to do the calendar in the browser as well. Super frustrating and confusing with 2 calendars that I can't merge in particular. I would like to get a notification when there is a universal solution to this very annoying problem.

Ken Graham wrote:

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?

In this Forum look back to 14 May and digest the post of MacSavvy. He/she offers two solutions. I used the solution number one and it worked for me. In your MacMail, under Account I had a choice of deactivating or deleting the account with the problem. I selected deactivation and proceeded, thinking that some day if Apple ever resolves the loop di loop problem I have the option to reactivate the account, if needed. Installing update 10.14.5 didn't help me at all.

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!

I followed your procedure to the letter. I went into MacMail accounts and selected my Google account. My Google account remained and remains with the squiggly symbol and the loop-di-loop windows continue to pop up. Maybe I didn't reactivate correctly. Please explain exactly what you referred to as the "online button" and where to find it. Thanks.

I am vinetc with a different apple account. If you followed the procedure you can click on the squiggly symbol and it will reactivate without the loop.

If not, try again deleting the same items and it should work.

I just got done speaking with apple support and they resolved the "failed to authenticate" issue I was having with the mail. Here is the screenshot of what they told me to do...After I restarted my Mac I went and logged back into the Mail/Gmail account and everything worked!

To all that are struggling with the GMail authentication problem, the above fix posted by RNH92 is what resolved my GMail authentication problem (see my earlier post) with NO further issues for more than a month that has also included the update to 10.14.5. No need to delete and/or create new accounts.

Great it worked for you. Actually, vinetc posted the same solution 10 days ago but it didn't work for any of my 16 gmail accounts :| . I'm on a new MacBook Pro, still under the 15 day return guarantee.

I found a way to eliminate the endless loop. 

1. On your MacBook go to>system preferences, then choose >internet accounts. 

2. Click on Gmail and then choose the remove “—“ at the bottom. If Gmail cannot be highlighted/removed, first select “mail” under Google In the right hand pane, then select remove. Once you select remove, it will ask if you want to remove all data from the account. Select>Okay. 

3. Close system preferences

4. Open Mail. Choose Mail>Add Account and select Google Mail and continue. 

5. Once Gmail is installed in Apple mail, sign into Google and add the accounts back onto your MacBook.

I've been having the same issue since I update the software today. I started following your tip but when I select all that's related to my account, wouldn't that mean I will erase all the saved passwords on the keychain related to my gmail account?

Did this happen to you?

Thanks!

This has happened to me twice. I found a solution that works and hope I remember it next time. The problem is an authentication issue - for some reason Apple randomly flags the gmail password as expired and denies access. This can be fixed in keychain - search in keychain for gmail or your gmail account. One of the search results will contain the word "expiry". Delete that line and you are back in business - you will be able to re-add the account with no authentication issue if you had deleted it in mail.

Is there a reason why the explanation from lazy-ants (on April 2) in this same thread does not work for you? Followed that twice - once after 10.14.4 failed to authenticate and again after 10.14.5 was installed and had repeated login failures.

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.