Mac Mail App Broken for Some Gmail Users in macOS Mojave 10.14.4

Apple earlier this week released macOS Mojave 10.14.4, which has had the unfortunate side effect of rendering the Mail app unusable for some who use Gmail services for their email addresses.

After installing the macOS 10.14.4 update and opening the Mail app, Gmail users are asked to authenticate their email addresses using a Google web login form.

Unfortunately, the authentication process does not stick, and shortly after authenticating, the Mail app asks for authentication once again or refuses to work, listing all Gmail accounts as offline.

There are threads on the Apple support forums and the MacRumors forums from users who are experiencing this issue, and we here at MacRumors have also run into the problem firsthand. MacRumors reader dwfaust describes the bug:
I updated to Mojave 10.14.4 yesterday and all seemed good. This morning I woke up to most (5 of 7) Gmail accounts "offline" and prompting for login credentials "in Safari".

I went through the process of entering email addresses and passwords, and the accounts are still offline.
Whenever I try to take them online, I get prompted for the logins again, but they won't come back online.

Rebooted twice, but no go.
Some users have had success setting up their email accounts using IMAP as a workaround. Those who have contacted Apple support have been told that a fix is in the works, so the bug could be addressed in the near future.



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20 weeks ago
[edit] Google has now fixed the issue so the following workaround is no longer necessary.

i'd definitely be interested, i sometimes use charles.

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.
[LIST=1]
* Download, install and run Charles ('https://www.charlesproxy.com/download/latest-release/').
* 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)
* From the Help menu choose SSL Proxying > Install Charles Root Certificate.
* 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.
* Back in Charles, from the Proxy menu choose SSL Proxying Settings.
* Add a new location with Host: people.googleapis.com.
* From the Tools menu choose Rewrite and click the Add button.
* Add a new location with Host: people.googleapis.com.
* 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)

* Once you save this, we're all set. Go to your system Internet Accounts or (Mail) and authorize your account.
* If everything thing is working, you can quit Charles and feel free to delete the certificate from Keychain.
Rating: 11 Votes
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20 weeks ago
That’s not a bug. That’s a feature.
Rating: 10 Votes
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20 weeks ago
I have a fix! Use iCloud mail :)
Rating: 7 Votes
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20 weeks ago
Eh, it’s whatever. I’m not worried. Haven’t kept anything of importance in my gmail account in a while, just annoying subscriptions.
Rating: 5 Votes
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20 weeks ago

I first noticed the issue on February 4th. It got slightly better with later betas.

https://forums.macrumors.com/threads/apple-seeds-second-beta-of-macos-mojave-10-14-4-to-developers.2168389/#post-27064233


I can verify the same. During beta testing of 10.14.4 I ran into the inability to log into Gmail. To solve it I first Quit Mail. I went to System Preferences/Internet Accounts, highlighted my Gmail account and deleted it with the minus (-) sign. I then Quit System Preferences. I then went back to the same setting again and added my Gmail account with address and password. I then rebooted for good measure. The problem didn't return. I recall that fiddling around in the Mail app itself solved nothing. Internet Accounts is what got messed up.

There have been some quirky little behind-the-scenes changes to macOS in 10.14.4 that have broken various things. I'm currently trying to sort out with a developer what Apple did to break the Command-C command when using ANY version of CopyPaste Pro. There are several little quirks in the latest version of Safari, evident if you visit YouTube and attempt to use the video playing interface. My experience with Apple is that this small stuff is of no interest to them, entirely fitting with my theory that they've failed to scale the Mac computer side of the company as the company has grown. I can toss out a dozen further examples. I find it all very annoying and wish they'd pay close attention to Mac again and return to focusing on the customer rather than whatever their distraction-of-the-day may be. :-(
Rating: 4 Votes
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20 weeks ago
Having been in technology all my life - bugs happen as much as we'd like them not to - all things are changing all the time. My issue is if this was discovered during Beta why wasn't it fixed before production. That is what Beta testing is about - having a large population testing a large variety of combinations, etc.
I have a few other issues like a game I play not working but it's last update was in 2012 so I probably should be surprised it was working this long. Apple should require that if something is still on the App store that the developers test during Beta and certify works or it gets pulled from store.
[doublepost=1553775847][/doublepost]

Never thought I'd say this, but Microsoft is looking better and better these days'. They now seem to be the more stable of the bunch.

Run windows 10 machines also and I'd never make that claim. It is no better than it ever has been
Rating: 4 Votes
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20 weeks ago
This has happened before, back in October and the problem was on Google's end.

It may be a coincidence that this happened right after the update, but it's definitely a case of deja vu.

https://forums.macrumors.com/threads/internet-account-google-failed-to-authenticate.2146470/
Rating: 4 Votes
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20 weeks ago

I would have expected an update from Apple by now. Surely this is an easy fix. Do they think users can just wait days because Gmail is accessible other ways?

There's no such thing as an easy fix. This is probably broken because someone thought something else was easy to fix and this broke as a result.

Any patch needs to be QA'd, and that will take a cycle or two. I just wish there was a better way for Apple to get the word out to people that there are known issues to be aware of so people didn't update and get hit with this in the mean time.

Thanks to MR for posting it. [s]At least I know I'm not crazy.[/s] At least this can't be taken as further evidence that I'm crazy.
Rating: 4 Votes
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20 weeks ago
We use GSuite on the company and a this sucks
Rating: 4 Votes
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20 weeks ago

I have a Fix. Use ProtonMail.

I have an idea. Why don’t people stop telling others to use mail service ‘x’ in defense of Apple’s blooper. It’s getting really pathetic always seeing people defend Apple when they screw up. How does this help make them a better company if they aren’t being held accountable? Workarounds do nothing but weaken an already splintered company.
Rating: 4 Votes
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