Level 1

134 points

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

Top-ranking reply

ctucek

Level 1

8 points

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.

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"
Now you see "Sign in to continue to Mac OS." Don't - It's a loop. Instead click on "Create Account" at the bottom.
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!

View in context

868 replies

lkrupp

Level 7

22,201 points

Jul 12, 2019 11:14 AM in response to Jedesache

Jedesache wrote:

This is the ONLY thing that fixed it for me! But this issue was with a q.com email address that was failing to authenticate. As soon as I disabled SOCKS Proxy and went to Mail to add the q.com email account it added instantly. This Mac was running 10.14.6. On another Mac running 10.14.3 SOCKS Proxy was NOT enabled and it has always been able to add the same account right away.

There are discussions around about the SOCKS Proxy enabling itself after every restart. It was tracked down to probable malware on the affected machine. Using the free version of MalwareBytes the malware was removed and the issue was resolved. I would urge any here with the authentication problem to check the status of their Network preference panel to see if the SOCKS Proxy is enabled. System Preferences->Network->Advanced->Proxies. If it is, turn it off and download the MalwareBytes app to check your system for malware. Now check if the authentication problem still exists.

Sep 23, 2019 7:37 PM in response to Ken Graham

I tried ALL THE THINGS, and no work-around has helped. I had resorted to just using Gmail and Google Calendar within Safari until Catalina came out, but when I looked up the projected release date, I found out that a public beta is available for download! I upgraded, and IT WORKS. My life can go on now. Here are the instructions I followed: https://www.techradar.com/how-to/how-to-download-and-install-macos-1015-catalina-beta-right-now

Sep 24, 2019 9:02 AM in response to Michka12345

"by clicking on « open safari » it was not going anywhere , if Mojave was installed correctly and safari / google would have opened asking to log in and then a new pop up screen asking you to allow Mac to access your gmail account and that is it !"

That's exactly the problem, but I don't think it has anything to do with "installed properly."

According to this thread, variations of not authenticating Google Internet Accounts has been a problem since 10.14.4, but it finally bit me on a password change shortly after an upgrade to 10.14.6 and the latest Safari.

You can tell it's specific to Apple's Internet Accounts authenticating to Google, because other apps using Google SSO (to the same corporate account), such as Zoom and Slack, redirect to Safari, open a Google authentication page, and log in successfully.

On the other hand, the redirection from Mail, Calendar, Internet Accounts... either don't open Safari, or if it is closed and quit, will open a start page with no URL - IE the redirection is failing.

Out corporate IT staff tried upgrading another Mac to 10.14.6 and found they could not add/update Internet Accounts, either.

Apple acknowledged to out IT that they know of the problem and are working on it - yeah, right - only 5 months!

paulof

Level 1

4 points

Mar 26, 2019 3:16 PM in response to nycross

@nycross' workaround about setting up a new account and manually setting imap/smtp settings worked for me and my G-Suite account 👍

Roc6220

Level 1

4 points

Mar 27, 2019 6:26 PM in response to Ken Graham

Had the same problem on 13" Mac Book Pro. This was a known problem with the beta version also. Turned of finger print ID for safari and I was finally able to login with Google.

Ph0bius

Level 1

4 points

Mar 29, 2019 3:42 PM in response to Ph0bius

After reboot open Mail.app and check new mail (left button or "Shift+Command+N"). In popup Safari window enter your credentials and grant access rights to Mail application.

gjdkeu

Level 1

75 points

Apr 1, 2019 8:14 AM in response to iacas

The issue is gone in MacOS 10.14.5 beta.

Apr 2, 2019 7:27 AM in response to lazy-ants

https://discussions.apple.com/thread/250259379?answerId=250259379021#250259379021

This worked perfectly 100% of the time. I had several accounts with this issue and this worked!

gjdkeu

Level 1

75 points

Apr 2, 2019 2:14 PM in response to Grant_Y

Same issue here. If you don’t minimize mail the issue is gone. This trick works for me.

Apple hopefully release a fix quickly, we hope.

mlierley

Level 1

8 points

Apr 4, 2019 5:40 PM in response to Ken Graham

I grabbed the mail App of a 10.14.1 machine (Mail version 12.4 (3445.104.8) and so far everything is working perfectly!

Apr 24, 2019 5:14 PM in response to Ken Graham

The only way i've gotten it to stick is by setting up a new user on my mac and then the authentication loop works.

gjdkeu

Level 1

75 points

Apr 30, 2019 6:39 AM in response to maximb

It seems that the Mail issues with Google is solved in Public Beta 4, the mail app is now version 12.4 (3445.104.11).

At last they fixed it. Cross my fingers. 🤓

filippo_

Level 1

19 points

May 16, 2019 5:27 AM in response to Ken Graham

For me .5 solved (24h without disconnections)

Jun 5, 2019 12:20 PM in response to krascow

Yes. Although google authorized the safari authentication my Mac did not because keychain had randomly decided my credentials had expired.

macendo

Level 1

9 points

Mar 26, 2019 9:42 AM in response to dboroditsky

I went to this apple page https://support.apple.com/contact, and clicked "Get Help" under "Talk To Us." After I logged in, selected my computer, and then selected "Installations & Updates," and entered my phone number, I received a phone call from a tech at apple immediately.

Hope this helps

This thread has been closed by the system or the community team. You may vote for any posts you find helpful, or search the Community for additional answers.

Mojave 10.14.4 fails to Authenticate Gmail account