Mojave 10.14.4 fails to Authenticate Gmail account

You know that Apple is like a clamshell, closed tight.

The good news is that it's fixed in MacOS 10.14.5. The release is very near.

This was a software issue. Safari has now been updated to v13.0.1 to fix this issue.

This morning I tried to access my g suite account via the mail app in macOS and it prompted me to re-authenticate. I did so and it just keeps asking me to do the same thing over and over again. I have 2 g suite accounts and the second account is working fine after the re-authentication. This account now stopped working on my iPhone, but I can access it through the web and it's not blocked. In the accounts section in macOS it "Enter the password for the account “(null)”. Google requires completing authentication in Safari.". When I click on Open Safari, it walks me through authenticating, and when I go back into accounts it says the same thing.

On the iPhone, it's saying to re-enter my password and I do via the google website (iOS takes me there when I click on the re-enter password button) and after entering it, it just takes me back to the same screen. It's like gmail isn't passing the token (or some data) to the device.

I tried to removing the account completely on my Mac and re-adding it, same thing. I tried to disabling access to macOS via the security settings on my account and then re-adding, same thing. I also tried to turning on 2-factor authentication...same thing, and then I turned 2-factor off and got the same thing.

I did setup the account using IMAP on my Mac for now and it's working fine, but no access to calendar or contacts.

I'm on macOS 10.14.4 and iOS 12.2.

I reverted back to 10.14.3 from a time machine backup. Turned off automatic updates and updated my changes made since the old backup. Everything works fine now.

So frustrating that Apple has let this slip through.

I was also able to get the Charles rewrite rule change to work, but with a slight variation.

For my GSuite account, the rewrite worked as described. No issues.

I also had an older personal account that had the same "fails to authenticate" issue, and for that I also had to add another rule to overwrite the response code to 200 (it was returning 404). Once BOTH rules were in place, I was able to add the once broken account.

Now all three Gmail account are working as expected.

Based on this, I'm thinking it could be more of a Google issue, exposed by changes made by Apple.

The native CalDav/IMAP approach worked for me in the interim until they fix this. Downside is you have to enable less secure apps, which you might not have the permissions to do. I was going to go down the Charles path, but this was just easier for me. Also sent feedback to Apple about the issue. At least there's some workarounds in the meantime-- Thanks to the folks that figured out the auth rewrite solutions. Much appreciated

The solution that seems to have worked for me is the Charles bypass. See here: https://forums.macrumors.com/threads/mac-mail-app-broken-for-some-gmail-users-in-macos-mojave-10-14-4.2175312/page-4#post-27232575

Hopefully there is an official fix soon!

I've actually managed to fix the issue by setting up a local proxy that fixes the authentication request URL, as posted earlier:

https://discussions.apple.com/thread/250259379?answerId=250498073022#250498073022

Problem is, this solution will scare and confuse your average Mac user. Disgraceful.

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

I tried to authenticate on my Mac and iOS again tonight and both worked! Earlier this week they weren't working, so it appears google fixed whatever was wrong with my account. I'd recommend trying it again.

Google changed their 2-step verification process for G Suite accounts within one day of the Mojave 10.14.4 release. Could be the culprit.

New 2-Step Verification options for G Suite accounts

March 26, 2019

What’s changing 

We’re updating how 2-Step Verification works for G Suite. This will make new 2-Step Verification methods available for some devices, and update the 2-Step Verification user interface on mobile and desktop devices. There are three key impacts:

• • New 2-Step Verification interfaces 
  • Different screens on different browsers (Safari, Edge, etc.) 
  • Expanded Bluetooth security key support 

https://gsuiteupdates.googleblog.com/2019/03/new-2-step-verification-options-for-g-suite.html

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.

• Sign in to your Google Admin console. ... 
• Click Security > Basic settings. ... 
• Under Less secure apps, select Go to settingsfor less secure apps.
• In the subwindow, select the Allow users to manage their access to less secure apps radio button.

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.

A fix that works for Mail:

Shut down you Mac and boot from your 10.14.3 backup. (all makes backups before upgrading ....uhh)

Start Finder an go to your MacHD -> Aplications and delete Mail.app (confirm with your PW). You can make a copy by pressing command-d before deleting it.

Copy Mail.app from backup (the one you have booted from) to the MacHD -> Applications folder.

Restart from your Mac.

Now 10.14.4 is using a Mail app that works. 🤓