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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 28, 2019 2:47 AM in response to QuietMacFan

I don't see how this editorial is helpful: Gmail works just fine with third party email apps, and the authentication flow isn't compromised. This only happens with Mail.app, Calendar.app and the internet accounts feature in System Preferences. The problem has only arisen since 10.14.4 was released, and it doesn't affect all G Suite / Gmail accounts, only some (I have two for example, both set up the same way, and one works, one doesn't).


Interestingly, I note that OAuth flows in other products sometimes go in an endless loop as well - for example, Disqus. The only thing I have divined is that these flows *always* go through a private browsing pop-up window in Safari, and they don't always "hand back" to the invoking system properly (i.e. Mail.app or whatever).

Mar 28, 2019 6:02 AM in response to miskeecare

Hard to say - I don't know how they implemented the Safari Auth - but you can clearly see - at least in my case that you can login in the safari window, sometimes there is even one page after login informing you about it and then after click safari is closed and immediately you get message about account "null". So it looks to me more like the information from safari are not provided into the Accounts...

Mar 28, 2019 6:37 AM in response to Ken Graham

Same here. Getting "Enter the password for the account (null)" when adding a G Suite account an a clear installation of a recent Mojave or getting a notification that account has been already added and showing the name of the regular gmail account that has been added and then removed before.


What's even more bizarre and made me really puzzled is, when I created a new user account (non admin), restarted, logged into the new account and tried adding a G Suite account (without setting up icloud or doing anything else) it tried to add that G Suite account, failed and displayed the name of my regular gmail account which was never entered on that brand new user account! How can it even be possible to get the name of my regular gmail address in that new account? For me looks like a potential security issue.


The workaround has already been mentioned: "Add Other Account" and add smpt/imap info manually. For that you might need either creating a password (when using 2-factor authentication) or allow "Less secure app access" in Google Account Security settings. Doesn't look as nice as a google account (i.e. "All mail" mailbox of a G Suite account isn't included in the global "All mail" mailbox, calendar or contacts isn't connected), but at least email works.


I'm extremely disappointed: first with getting serious unrecoverable hardware errors with my SSD after only like 16 months of usage of a macbook pro, and now getting such software errors which are hard to figure out unless using some Google Fu and landing on this helpful thread.

Mar 28, 2019 7:01 AM in response to ykus

Having the same problem. I access four different Gmail accounts, and only one of them- my PRIMARY account- is failing. Have tried removing/re-adding, clearing email cache, etc, all to no avail. When I add it back in- it seems to connect fine, but then I get the "Enter the password for the account "(null)"" message. I can login again in Safari, but nothing changes.

Mar 28, 2019 7:10 AM in response to Ken Graham

Hi, I have the same problem with my university account that uses a G suit. I was able to fix the problem on my iPad and iPhone using the exchange account with m.goole.com and a dedicated password. I would like to make the same on my Mac but I don't know what I have to insert when it asks internal url and external url. I tried with m.google.com but doesn't work. Have you got any solutions? do you know internal and external url for google?

Thanks

Mar 28, 2019 7:25 AM in response to Neowolfwitch

Trying all sorts of “voodoo” will not help the situation and may cause more trouble if you don’t remember all the things you tried . This is obviously something Apple and Google will have to resolve so sit back and wait patiently. Same advice for the “me too” posts. As for me, I’m not experiencing the issues described here. Thing only thing I was required to do is enter my Google credentials and all was well. That means not everyone is experiencing the same issues.

Mar 28, 2019 7:39 AM in response to lkrupp

Updated two Macs to 10.14.4 and right away one of my gmail accounts (the GSuite One) wanted to me to enter a new password and that goes into an endless loop. I could get the free gmail account to work. Initially the iPhone and iPad worked after updated to iOS 12.4, but when I changed the passwords on my two Gmail accounts, they could not longer work for either the free gmail account and the Gsuite gmail account and trying to update the passwords on iOS devices just dropped me back to the initial screen to add an email. Tried deleting accounts on Mac and iOS and re-add. Tried to clear the keychain of all items that contain gmail. Nothing works. I have had install the Gmail app on iOS and use webmail on the Macs to get my email.


Got out an old iPad and used it to change my Gsuite gmail account to the new password and IT WORKED, so the issue is changes in MacOS and iOS that don't work with the Google Authentication process. It might be that Google needs to make some change but it was Apple that released new MacOS and iOS updates, to support the release of Apple News+, that had this bug that had not yet been resolved in beta testing. So far no word from Apple despite 3 days and posts all over the internet on this issue.

Mar 28, 2019 7:53 AM in response to lkrupp

lkrupp wrote:Trying all sorts of “voodoo” will not help the situation and may cause more trouble if you don’t remember all the things you tried


Indeed, except people aren't doing this voluntarily, they're having to do it out of necessity because of a situation triggered by a system recommended/pushed update.


This is obviously something Apple and Google will have to resolve so sit back and wait patiently. Same advice for the “me too” posts.


You're right. But so far, the update hasn't been pulled. So there is, as far as we can tell, no official recognition that there is actually a problem, or even that a fix is in the works. So other users downloading the update will blindly fall in to the same situation. This is the concern of the 'me too' posts.


J

Mar 28, 2019 9:04 AM in response to Ken Graham

Having the same problem here.


As an independent contractor, I have a myriad of Google accounts for each company I work for.


The problem persists for any gmail account I have that is associated with a google business account. i.e. email issued to me from a company I work for that has a google for business account.


The problem did not occur with my personal gmail account. ...


Not sure that helps anyone, but there you go.

Mar 28, 2019 9:53 AM in response to Chattermedia

Frustrated with the lack of any response from Apple despite many posts across the internet, including this forum, I have taken my iPhone back to version 12.1.4 which is still signed. That completely eliminated the issue with the iPhone and I can enter the new password for both my free Gmail account and a GSuite email account and get mail for both in the mail.app. Will do the same with my iPad and may have to go to the lengthy process with my two Macs to go to an earlier version of the software. It should not be like this. Of course that means I can not use Apple News+ but it was not worth upgrading to use it considering the troubles it caused.

Mojave 10.14.4 fails to Authenticate Gmail account

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