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 Dec 27, 2019 11:41 AM

This worked for me on 8 different Gmail accounts. The glitch happened last night 26Dec19 when I installed a Mojave upgrade.

Note: I am running Mojave 10.14.6, Safari 12.1.2, and Mail 12.4 which may be why it was this simple.


  1. In "Mail," click on the tilde next to the account now connecting. It will pop up a box saying, "Enter the password for the account “**************@gmail.com”. Click on "Open Safari"
  2. Now you see "Sign in to continue to Mac OS." Don't - It's a loop. Instead click on "Create Account" at the bottom.
  3. Don't create a new account. Look below (lower left) and click on "Sign in Instead." It will reopen a log-in box for your Google account.

4. Log in to Google with your email and password (two pop up boxes in a row).

5. It will pop up Google’s "Protect your account." Click on "Confirm"

6. New pop up window, "macOS wants to access your Google Account." Click on "Allow."


Your “Mail” screen will pop to the front and the tilde will be gone. Your mail will now function. Do a test and it should come through.


For those using the same specs as my Mac, hope this works for you also. Since I had 8 accounts to fix, it seems true (but it was one laptop with particular specs). I actually stumbled upon trying this before any solution offered - God's grace maybe. If it works for you, send Him a "thanks."


Merry Christmas!

868 replies

Mar 26, 2019 2:06 PM in response to Ken Graham

Google support was able to resolve this issue for me, or at least provide a suitable workaround for my accessing mail*.


We were able to delete the account and them re-add it as an IMAP account as follows**.


User name: full email address

Incoming server: imap.gmail.com

Outgoing server: smtp.gmail.com


*Please note that this does not resolve calendar or contact syncing.

**Gmail must be set to allow less secure applications. This setting can be enabled in the Gmail web client under settings/security


Mar 28, 2019 3:44 PM in response to Ken Graham

Hi everyone,

I found a solution that worked for me, no need to delete accounts or set up new IMAP accounts. The trick that did it for me, on two different Macs for several different accounts, both @gmail.com and @mydomain.com (hosted by Google) accounts, was to go through the Internet Accounts pane in System Preferences and NOT through the Mail app itself.

Here are the steps I went through:


  1. Open System Preferences and go to Internet Accounts.
  2. Select the Gmail account that is refusing to log in.
  3. Then, select one of the options that is not selected like Contacts or Calendars (I only use mail but not Contacts, Calendars, Notes so all these are not selected for me).
  4. Then, I received a notification from macOS that I need to authenticate the account with the two options to 'Close' or to 'Continue'. Do NOT click continue just yet.
  5. Quit System Preferences.
  6. Then click 'Continue' on the Notification.
  7. This will open System Preferences again (don't ask me why but if you don't close System Preferences before clicking 'Continue' it doesn't work) and a notification within the Internet Accounts pane pops up linking to Safari and the known Google Authentication process.
  8. Go through the steps of entering your password and two-factor authentication etc. and then, sure enough, the account is logged in again also in Mail.


As stated above, this worked for several of my accounts on two different Macs and now all accounts are logged in again and work fine.


I really hope that this will work for others as well until the issue with the Mail app is fixed. Good luck!!!!!

Mar 29, 2019 5:39 AM in response to Ken Graham

I am also having this problem.


I have two Gmail accounts (let's call them A and B). I also have two macs (let's call them 1 and 2).


I updated Mac 1 and 2 to 10.14.4 at the same yesterday.


After the update, on both Macs my Gmail accounts had disappeared entirely from the Internet Accounts System Preferences pane. I re-added them.


On Mac 1, I was able to successfully re-add BOTH accounts. Both worked perfectly.


On Mac 2, I was only able to re-add account B. Account A got stuck in this endless of authentication failures with the "(null)" error.


It's worth noting at this point that account B is a regular @gmail.com account, whereas account A uses a custom domain to login to Google.


I spoke at length to Apple customer services who assured me that their engineers are aware of the issue and are working on a fix. Why this slipped through the net even though it was apparently an issue ion the pre-release Beta is beyond me!


They advised me the problem was more common with accounts from GSuite/Google for Business, or accounts with custom domains.


They also suggested I try something which apparently has worked for some people: delete all Google accounts from System preferences. Then remove all references to Gmail and Google from Keychain. Then restart. Then re-add them to Internet Accounts in System Preferences. This didn't work for me.


---


UPDATE: On Mac 1 (the one where both accounts were working) I later discovered secondary issue. Although I was able to received and send email with Gmail account A (custom domain) I wasn't able to send zip file attachments! See attached screenshot.


A further bug was that in the error message (as shown in the screenshot) shows, there isn't a space between the word "visit" and "https://" and so it thinks "visit" is part of the URL, so clicking on the link doesn't work!


---


UPDATE 2: after restarting Mac 1 it now is stuck in the cycle of asking me for my password for Gmail account A again. However, when I do enter my password, it is successful and I don't see the (null) error. But moments later it forgets it again. So, still a problem, but totally different behaviour to Mac 2.... at least on Mac 1 I can see all my old emails in Mail. On Mac 2 I have nothing!


Mar 29, 2019 7:28 AM in response to drsalomon

I had the same behavior after the update: GSuite mail and calendar not working, gmail.com mail and calender work okay.


The mail is not a big deal to me because I use Postbox mail client. If you switch to Postbox, Thuderbird, or other non-Apple mail you can work around the problem... and maybe have a better experience long term.


The calendar was a harder problem, but I found a workaround that works for me. I delegated my GSuite calendars to my gmail.com account and now I can get to all of my calendars in MacOS Calendar. - via my gmail.com account.


By "delegate" I mean:

  • in your GSuite calendar (at calendar.google.com) choose Settings and sharing
  • "Share with specific people" choose "Add people" and add your gmail.com account
  • choose "Make changes and manage sharing".


If you don't have that option, it must be enabled by your GSuite administrator, which they may or may not be willing to do. I administer the two GSuite domains that I couldn't authenticate with 10.14.4, so it was possible for me to enable this workaround.


Mar 29, 2019 10:51 AM in response to Ken Graham

I have a personal gmail account on two Macs with two-factor authentication. This worked on both and is mentioned earlier - but I could not find it to reference:

1) Open System Preferences->Internet Accounts

2) Click on Gmail Account. It immediately opens a dialog box with "Open Gmail in Safari". Click this.

3) Safari opens and prompts with your user name in the gmail login. Click Next

4) Safari gmail login asks for Password, type it in, then click Next

5) Safair gmail login asks for 2-factor key. Type it in and click Done.

6) Mail was already open and updated the Gmail mailbox instantly.

This worked for both Macs.


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.

Apr 1, 2019 10:17 AM in response to Ken Graham

I've also had this issue since I updated my OS to Mojave 10.14.4. But finally I was able to have it fixed.


I found this google link https://support.google.com/accounts/troubleshooter/3178296?hl=en and after answering the questions there, I ended up seeing the following text with this magic link https://www.google.com/accounts/displayunlockcaptcha:

...

To grant access to your Apple device, go to your web browser and follow the instructions to allow a new application to access your account.


Clicking on the link and following the steps, I got to a page stating:


Account access enabled


Please try signing in to your Google account again from your new device or application.


At this time, I went back to my Mail app and tried to authenticate again using the account with the issue. So I was redirected to google's login page on Safari where I had to put my email/password and login. After that I went back to Mail and finally no dialog showed up asking me to authenticate again as before. So I went to Mail settings and confirmed the account status was online. But to make sure, I closed and opened the Mail app, checked the account status again, exchanged some emails and no issues so far.

Apr 10, 2019 11:44 AM in response to Joseph Masselli

Yesteday i installed the 10.14.4, then my google account did not work with Calendar and Contacts. Then i try some solution what i found on forums. None of them worked. Then i try to delete the gmail account from internet accounts preferences panel. Then i try to add it again. It has failed. Next i try to uninstall the Hands off application (a network watch and control app like Littlesnitch), then a computer restart and voilá, then I was able to add my gmail account successfully.

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Mojave 10.14.4 fails to Authenticate Gmail account

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