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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 30, 2019 8:09 AM in response to lkrupp

I initially thought that Apple servers might be involved in the authentication process so they wouldn't need to roll out an update. But on further reflection, the G-Suite Gmail authentication process is handled by Google. So I think you're right. I hear that this bug came and went during the 10.14.4 betas all the way back to January.

Mar 30, 2019 8:30 AM in response to fft1024guy

fft1024guy wrote:

I initially thought that Apple servers might be involved in the authentication process so they wouldn't need to roll out an update. But on further reflection, the G-Suite Gmail authentication process is handled by Google. So I think you're right. I hear that this bug came and went during the 10.14.4 betas all the way back to January.

I wish, just for once, that we would get an official explanation from either Apple or Google as to what actually happened. This issue caused a lot of headaches for some people and they deserve an explanation. Doesn’t matter on whose end the trouble was, we just need to know.


It also hammers home the frequently offered advice to sit back and wait a while before applying any new update of any software one relies upon. Wait and see what, if any, issues arise before jumping in, especially if your workflow might be disrupted.

Mar 30, 2019 12:19 PM in response to Ken Graham

Had two G-Suite accounts on different domains just stop working after updating, not immediately nor at the exact same time.


Attempting to reconnect appeared to work correctly until Safari closed and I got a "Incorrect username" pop-up from System Preferences.


I ended up deleting the accounts and re-adding in System Preferences and everything is now working.

But...


Both accounts display an alias email address in System Preferences -> Internet Accounts. Previously the displayed address was the primary email addresse, i.e. the one entered during the authentication process. Changing the "From" address was easy enough to fix in Mail -> Preferences but that should have been unnecessary.


Whether this is a problem at the Google end or the macOS end is not easy to decipher but it is definitely WRONG behaviour somewhere.

Mar 30, 2019 1:33 PM in response to Ken Graham

I still have an issue where the credentials from another gsuite account are being picked up when authenticating. For example, if I login with credentials for account A, I authenticate, but it gets added as account B; email doesn't work. When I authenticate with account B, everything works fine, but when I try to add account A, it tells me, account B is already added. Anyone know how to remove this invalid reference?

Mar 30, 2019 2:03 PM in response to loopless

Sorry, the problem has NOT been "fixed".


My WORKAROUND was to delete and recreate the accounts (currently waiting for a few 100k mail items to synch...) but my accounts now display an alias (WRONG) email address (account name for Google) in the account details. I had to manually correct this email address in Mail preferences.


Yes it works... but not correctly



Mar 30, 2019 5:14 PM in response to Ken Graham

Dear all, I found a workaround that can be helpful until Apple releases a fix for MacOS Apple Mail.


Important: for those users who have two factor authentication enabled on their Gmail or G Suite accounts, there's no need to disable 2FA on your accounts to apply the configurations I'll describe below


Basically you will have to remove you existing Gmail account from Apple Mail and reconfigure the account as a new IMAP account.


A- Those G Suite users who have 2FA enable will have to make sure that "less secure apps is enable" for their accounts.


1. Login to your G Suite Admin Console(admin.google.com). 

2. After that go to Security > Basic Settings > Go to settings for less secure apps ›› 

3. Select the middle option 'Allow users to manage their access to less secure apps'. 

4. Save changes. 


Once this is done, please do the following

1. Go to Gmail.com 

2. Login to your source G Suite account

3. Open a new Tab 

4. Go to this URL https://myaccount.google.com/lesssecureapps 

5. Toggle the Less secure apps option and make sure it's enabled. 


B- Create an App Password for your Mail App (16-digit passcode)

Instructions here: https://support.google.com/accounts/answer/185833


C- After this is done, remove the affected G Suite account from Mac Apple Mail and add it back again manually instead of selecting 'Google' option by using the settings and steps listed as per this Help Center support article https://support.google.com/mail/answer/7126229?hl=en


Important notice: Please be mindful that IMAP protocol only syncs you emails and not contacts & calendars.


Mar 31, 2019 11:04 AM in response to Ken Graham

It is fixed!!!!


On both my iOS devices and my MacBook Pro.


I didn't do anything.


I found out by accident.


Because of some syncing difficulties, I had to delete the Exchange account from my iPhone that Google suggested as a work around. On a lark tried to reinstall as a Google account, thinking it probably would not work and I would have to go the Exchange route again. It worked. Installed as a Google account and everything is normal. Same with my iPad.


I had already deleted the Google account on my Mac pending a fix by Apple. But thought I would give it a try. It worked. Installed normally without the endless loop and null messages. I wonder if Google made some changes as there are no Apple OS updates.


Hope the same is true for everyone else. Try deleting and reinstalling your Google accounts. I know that didn't work before, at least for me. I tired that several times. But I think something changed on Google's end.


Yah!!

Mar 31, 2019 3:06 PM in response to Scott Willsey

You forget to point out that ALL software has bugs no matter WHO developed it. Google certainly does not have an immaculate track record for buggy software. Google got caught programming around Safari’s security protections so they could continue to glean user data. Neither does Microsoft, or Adobe, or any other developer. The impulse to immediately blame Apple for everything is tempting but counter productive in the end.

Scott Willsey wrote:

Now are we done blaming Apple TV+ for this yet?

Seriously. Software bugs happen. Apple always have had them. They always will.

Mar 31, 2019 3:12 PM in response to lkrupp

True. I meant to imply it when I said software has bugs. I was responding to earlier complaints about Apple’s focus. I’m not trying to pin the blame on Apple for this, indeed it doesn’t seem like it was their issue per se, although it’s not really conclusive at this point.


I just found the moaning about Apple’s focus and News+ or whatever the complaint was wrt this issue illogical.

Mojave 10.14.4 fails to Authenticate Gmail account

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