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Ken Graham Author

Level 1

131 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

yana131

Level 1

4 points

Posted on Apr 23, 2019 7:05 PM

Thanks to mulberrywriter for the answer .

Most easiest way without downloading and deleting accounts.

Go to your gmail account in browser.
There is a little gear in your gmail under all emails (I did this way so explain step by step from my side)
Choose Settings under that gear
Choose Account and Imports
Choose Other Google Account settings
Choose Review your privacy settings.
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.
Do not logout. Go to Mail and Click on Lighting icon near your account.
Click everything it will ask.
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.

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868 replies

Apr 8, 2019 8:20 PM in response to Ken Graham

I am unable to connect a calendar because "Google requires completing authentication" and it doesn't want to recognize my email. Consequently, the calendar won't sync. This happened after updating to 10.14.4

adamp00

Level 1

4 points

Apr 9, 2019 3:13 AM in response to Ken Graham

Change the "check for new messages" from 1-minute to 5-minutes, it makes a huge difference on your system

I have 4 gmail accounts set up, and Mail has gone from constantly-logging (see in Console) to far far less, making the system usable again...

Waiting for a proper fix, but this helps.

Apr 9, 2019 8:55 AM in response to muctau

I'd like to try your method however my window only offers the Outgoing Mail Server )SMTP) and nothing else. Am I correct that this window is in the Mail Preferences under Server Settings or is there another like window elsewhere? Thanks.

tib0r

Level 1

4 points

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.

Apr 11, 2019 7:39 AM in response to Ken Graham

I was able to authenticate, but now I have to keep quitting mail to get it to reconnect, then it goes offline after a bit. I set the google settings to less secure as some suggested, but please Apple, this is really annoying, figure out a fix and send the update!

Apr 11, 2019 8:03 AM in response to sarafrommaplewood

Hi Sara, I would like to try your method and see if my iMAC will authenticate. Exactly what Google settings did you change to less secure? Agree that this is an annoying issue and Apple needs to get to work! Thanks in advance.

Apr 11, 2019 10:03 AM in response to Joseph Masselli

This hasn't completely solved the issue, but I no longer get the authentication window. My gmails just continuously go off line. If I quit Mail and open it again, they go back on line, but it's annoying for sure.

wales34

Level 1

4 points

Apr 11, 2019 2:56 PM in response to Ken Graham

Same problem here. What fixes it each time I log on in Apple Mail, is I double-click the squiggle icon next to the Gmail inbox in Apple Mail, and suddenly Gmail works in sending and receiving mails. But it's not fixing it permanently.

Apr 12, 2019 2:17 PM in response to SuzyC33

It appears that Google is now enforcing two-factor authentication for Mac Mail users, using your cell phone as the medium for authentication.

It has been doing so with web Mail for some time.

It's a bit of a pain, especially if you miss the pop up message, but I understand the reason.

gjdkeu

Level 1

75 points

Apr 13, 2019 12:43 AM in response to Bruce Mann

Same issue here. I did make at copy of Mail app from 10.14.3 and renamed it MailOld and copied it to the App folder. Launched it and all is back to normal.

Mail app from 10.14.4 should NOT have been released. Apple must have got a brain tumor.

Lussac

Level 1

4 points

Apr 13, 2019 1:29 AM in response to gjdkeu

This is what I did when I wasn't getting anywhere but before doing that I gave Spark a try just in case I couldn't get Mail working again. Spark worked straight away after downloading but am back to using the previous version of Mail from my backup and that works just fine.

Apr 13, 2019 7:52 AM in response to Ken Graham

The error doesn't occur if you setup a new user account. Works just fine with authenticating and setting up the same account. So there's something associated with the user library folder and authentication. A certificate... something. My next test is to delete all internet accounts, destroy and create a new keychain for the user. Go in to the ~Library/Mail folder and destroy all leftover folders from those deleted email accounts. Then I'll try again.

if that doesn't work... i'll just migrate all the user data to a new user minus the ~library folder.

Apr 13, 2019 7:54 AM in response to gjdkeu

if that doesn't work... i'll just migrate all the user data to a new user minus the ~library folder.

Apr 13, 2019 9:32 AM in response to Lussac

I have been trying to download Spark to my iMAC but for some reason it doesn't download from the Apple Store. Is there some secret procedure that I'm not aware of? Or maybe it isn't available any longer. Can you help? Thanks.

Lussac

Level 1

4 points

Apr 13, 2019 9:39 AM in response to Joseph Masselli

No, I just went to the App Store, did search for Spark and found "Spark - Email App by Readdle" and clicked on "Open" and it downloaded and installed as normal. Just looked and it seems to be OK from the UK at least and downloaded to my macbook with no problem.

Mojave 10.14.4 fails to Authenticate Gmail account