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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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Posted on Mar 29, 2019 10:52 AM

Someone with the handle Gannett posted a fix on the MacRumors website and it worked for me. I don't know how to link directly to his post so I'm pasting his instructions below. The fact that he figured out a solution shows just how neglectful Apple has been about this problem.


Anyway, these are Gannett's instructions:


Okay, so I've tried to make this as easy as possible. We're going to use Charles to rewrite a response from google to include the email address which is for some reason missing in google's own response. This is a one time setup only needed for verification.

  1. Download, install and run Charles.
  2. If this is your first time using Charles it should prompt you to authorize automatic proxy configuration. Do this. (Otherwise just make sure the macOS proxy is enabled and working)
  3. From the Help menu choose SSL Proxying > Install Charles Root Certificate.
  4. Once the certificate is installed, find it in your keychain (type Charles into the search), open it, expand the Trust section and set to Always Trust. You will be prompted for your password when closing it.
  5. Back in Charles, from the Proxy menu choose SSL Proxying Settings.
  6. Add a new location with Host: people.googleapis.com.
  7. From the Tools menu choose Rewrite and click the Add button.
  8. Add a new location with Host: people.googleapis.com.
  9. Add a new action with the following details...
    • Type: Body
    • Where: Response
    • Replace Value: {"names":[{"metadata":{"primary":true},"displayName":"Your Name"}],"emailAddresses":[{"value":"your@email"}]}
    • (Make sure you put in your name and email address)
  1. Once you save this, we're all set. Go to your system Internet Accounts or (Mail) and authorize your account.
  2. If everything thing is working, you can quit Charles and feel free to delete the certificate from Keychain.

868 replies
Question marked as Best reply

Mar 29, 2019 10:52 AM in response to Ken Graham

Someone with the handle Gannett posted a fix on the MacRumors website and it worked for me. I don't know how to link directly to his post so I'm pasting his instructions below. The fact that he figured out a solution shows just how neglectful Apple has been about this problem.


Anyway, these are Gannett's instructions:


Okay, so I've tried to make this as easy as possible. We're going to use Charles to rewrite a response from google to include the email address which is for some reason missing in google's own response. This is a one time setup only needed for verification.

  1. Download, install and run Charles.
  2. If this is your first time using Charles it should prompt you to authorize automatic proxy configuration. Do this. (Otherwise just make sure the macOS proxy is enabled and working)
  3. From the Help menu choose SSL Proxying > Install Charles Root Certificate.
  4. Once the certificate is installed, find it in your keychain (type Charles into the search), open it, expand the Trust section and set to Always Trust. You will be prompted for your password when closing it.
  5. Back in Charles, from the Proxy menu choose SSL Proxying Settings.
  6. Add a new location with Host: people.googleapis.com.
  7. From the Tools menu choose Rewrite and click the Add button.
  8. Add a new location with Host: people.googleapis.com.
  9. Add a new action with the following details...
    • Type: Body
    • Where: Response
    • Replace Value: {"names":[{"metadata":{"primary":true},"displayName":"Your Name"}],"emailAddresses":[{"value":"your@email"}]}
    • (Make sure you put in your name and email address)
  1. Once you save this, we're all set. Go to your system Internet Accounts or (Mail) and authorize your account.
  2. If everything thing is working, you can quit Charles and feel free to delete the certificate from Keychain.

Jul 25, 2019 6:22 PM in response to thee_spectacles

***Note: you will lose all of your saved keychain passwords. Make sure you have them available elsewhere.


  1. Open Keychain Access, which is in the Utilities folder within the Applications folder.
  2. From the Keychain Access menu, choose Preferences.
  3. Click General, then click Reset My Default Keychain.
  4. Authenticate with your account login password.
  5. Quit Keychain Access then Restart your computer.




Mar 29, 2019 3:25 PM in response to Ken Graham

After upgrade to 10.14.4 (10.14.5 Beta too) found at least problems:

  1. Problem with Gmail;
  2. Permanently crash mobileactivationd with 10 sec interval with high CPU usage (for create crash report);
  3. Language switch not working with configured hot key.


Solution for me (according to https://discussions.apple.com/thread/7420228?answerId=29625454022#29625454022):

  1. In rescue mode reset "restricted" flag with following command: chflags -R norestricted /V*/*/S*/*/Caches
  2. Reboot
  3. Rebuild sandbox app cache with following command: sudo /usr/libexec/*/app_sandbox_cache_builder --rebuild-cache
  4. Restore "restricted" flag in rescue mode: chflags -R restricted /V*/*/S*/*/Caches

Apr 23, 2019 7:05 PM in response to Ken Graham

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.

Mar 26, 2019 8:31 AM in response to Ken Graham

I'm having the same issue with my company's G Suite account starting today, after updating to 10.14.4.


Mail and Calendar both require my password as soon as I log in again. Added another G Suite account, it worked fine.


My company uses G Suite with OneLogin as SSO. The log in process seems to work fine.


Enter the password for the account “(null)”.

Google requires completing authentication in Safari.



Mar 26, 2019 9:25 AM in response to macendo

UPDATE:

I contacted Apple and spoke with a tech support person, shared my screen so he could see what was happening. He verified that it is legit. Continuing with the process for each account, I was able to get my accounts online.

IF for some reason you do not get the prompt, click the sideways lightning strike (my description) next to the account that's offline, and you should then get the prompts to authenticate.

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


Apr 2, 2019 12:22 AM in response to Ken Graham

Finally a 100% working solution is very simple.

In safari: logout from your google suite account (to make sure you will fix the right one).

Go to https://accounts.google.com/DisplayUnlockCaptcha to repair the access (documented on https://support.google.com/accounts/answer/2461835?hl=en)

after fixing add the account in the mac os settings or over the mail app as usually (you don't even need to delete it first if it's already added).

After verification in the opened safari window everything will go well.


The trick was simply to fix the password with the google link

Mar 27, 2019 8:13 PM in response to GilroyTech

Apple's email works fine with any legitimate email provider.


When I got my first Imac (El Capitan) i had to call apple to get gmail disabled. Gmail had "hacked" security so that it intermittenly failed, causing my appleid to malfunction (crippling the apple somewhat).


After a call to apple, who has wonderful support and diablo'ed gmail: everything worked perfect.


Gmail is run by an apple competitor and very political in nature. They can an will change "protocols" to cause intermittent failure.


As for other "email providers", there's plenty of them that all work perfect.


If "none of them work" then you either need to factory reset your apple (note: save your personal data first!) or you need to learn how to set up email accounts. (there are many many articles on how to do this to find on apple's pages)


such as:


https://support.apple.com/en-us/HT201320 (iphone)


https://support.apple.com/guide/mail/add-or-remove-email-accounts-mail35803/mac


email providers require an site, a user login, some email providers require password and then also "security protocol choice", some even a port setting - some two port settings. you have to check your provider for instructions how to use their service. Apple works with any service that uses industry standard email: but there is no industry standard to set settings, you have to enter those yourself.


you didn't say you tried Apple's iCloud email


it's a wonder you even mentioned Gmail doesn't work since Apple certainly is not google and google does sell products aimed to "end apple"


Mojave 10.14.4 fails to Authenticate Gmail account

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