mailappiconApple 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.

Top Rated Comments

supremedesigner Avatar
76 months ago
That’s not a bug. That’s a feature.
Score: 11 Votes (Like | Disagree)
Gannet Avatar
76 months 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.
Score: 11 Votes (Like | Disagree)
coolsean20 Avatar
76 months ago
I have a fix! Use iCloud mail :)
Score: 8 Votes (Like | Disagree)
TMRJIJ Avatar
76 months 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.
Score: 6 Votes (Like | Disagree)
Analog Kid Avatar
76 months 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.
Score: 4 Votes (Like | Disagree)
JcAzcanio Avatar
76 months ago
We use GSuite on the company and a this sucks
Score: 4 Votes (Like | Disagree)

Popular Stories

Generic iOS 19 Feature Mock Light

iOS 19 Leak Reveals All-New Design

Friday January 17, 2025 2:42 pm PST by
iOS 19 is still around six months away from being announced, but a new leak has allegedly revealed a completely redesigned Camera app. Based on footage it obtained, YouTube channel Front Page Tech shared a video showing what the new Camera app will apparently look like, with the key change being translucent menus for camera controls. Overall, the design of these menus looks similar to...
2024 iPhone Boxes Feature

Apple Changes Trade-In Values for iPhones, iPads, Macs, and More

Thursday January 16, 2025 6:45 am PST by
Apple today adjusted estimated trade-in values for select iPhone, iPad, Mac, and Apple Watch models in the U.S., according to its website. Some values increased, while others decreased. The changes were not too significant, with most values rising or dropping by $5 to $50. We have outlined some examples below: Device New Value Old Value iPhone 15 Pro Max Up to $630 U ...
2024 App Store Awards

Apple Explains Why It Removed TikTok From the App Store in the U.S.

Sunday January 19, 2025 6:58 am PST by
Apple on late Saturday removed TikTok from the App Store in the U.S., and it has now explained why it was required to take this action. Last year, the U.S. passed a law that required Chinese company ByteDance to divest its ownership of TikTok due to potential national security risks, or else the platform would be banned. That law went into effect today, and companies like Apple and Google...
Generic iOS 18

Everything New in iOS 18.3 Beta 3

Thursday January 16, 2025 12:39 pm PST by
Apple provided the third beta of iOS 18.3 to developers today, and while the betas have so far been light on new features, the third beta makes some major changes to Notification Summaries and also tweaks a few other features. Notification Summary Changes Apple made multiple changes to Notification Summaries in response to complaints about inaccurate summaries of news headlines. For...
iOS 19 Roundup Feature

iOS 19 Rumored to Be Compatible With These iPhones

Saturday January 18, 2025 10:28 am PST by
iOS 19 will not drop support for any iPhone models, according to French website iPhoneSoft.fr. The report cited a source who said iOS 19 will be compatible with any iPhone that can run iOS 18, which would mean the following models: iPhone 16 iPhone 16 Plus iPhone 16 Pro iPhone 16 Pro Max iPhone 15 iPhone 15 Plus iPhone 15 Pro iPhone 15 Pro Max iPhone 14 iPhon...
iPad Pro vs iPhone 17 Air Feature

Here's How Thin the iPhone 17 Air Might Be

Friday January 17, 2025 3:38 pm PST by
For the last several months, we've been hearing rumors about a redesigned version of the iPhone 17 that Apple might call the iPhone 17 "Air," or something along those lines. It's going to replace the iPhone 17 Plus as Apple's fourth iPhone option, and it will be offered alongside the iPhone 17, iPhone 17 Pro, and iPhone 17 Pro Max. We know the iPhone 17 Air is going to be super slim, but...
airtag 4 pack blue

AirTag 2 Launching This Year With These 3 New Features

Sunday January 19, 2025 8:11 am PST by
After a four-year wait, a new AirTag is finally expected to launch in 2025. Below, we recap rumored upgrades for the accessory. A few months ago, Bloomberg's Mark Gurman said Apple was aiming to release the AirTag 2 around the middle of 2025. While he did not offer a more specific timeframe, that means the AirTag 2 could be announced by the end of June. The original AirTag was announced...
apple power beats pro 2

Powerbeats Pro 2 Coming Soon: Apple to Announce Them 'Imminently'

Sunday January 19, 2025 8:25 am PST by
In September, Apple said that it would be launching Powerbeats Pro 2 in 2025, and it appears the wireless earbuds are coming very soon. Powerbeats Pro 2 images found in iOS 18 code In his Power On newsletter today, Bloomberg's Mark Gurman said the Powerbeats Pro 2 are "due imminently." In addition to Apple filing the Powerbeats Pro 2 in regulatory databases last month, Gurman said Apple is...