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
86 months ago
That’s not a bug. That’s a feature.
Score: 11 Votes (Like | Disagree)
Gannet Avatar
86 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
86 months ago
I have a fix! Use iCloud mail :)
Score: 8 Votes (Like | Disagree)
TMRJIJ Avatar
86 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
86 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
86 months ago
We use GSuite on the company and a this sucks
Score: 4 Votes (Like | Disagree)

Popular Stories

iOS 26

iOS 26.1 Coming Soon: New Features for Your iPhone and Release Date

Monday October 27, 2025 7:55 am PDT by
The upcoming iOS 26.1 update includes a handful of new features and changes for iPhones, including a toggle for changing the appearance of the Liquid Glass design, "slide to stop" for alarms in the Clock app, and more. Below, we outline key details about iOS 26.1. Release Date Given that Apple has yet to seed an iOS 26.1 Release Candidate, which is typically the final beta version, the...
iOS 26

6 New Things Your iPhone Can Do in iOS 26.1

Wednesday October 29, 2025 4:22 am PDT by
Apple is about to drop iOS 26.1, the first major point release since iOS 26 was rolled out in September, and there are at least six notable changes and improvements to look forward to. We've rounded them up below. Apple has already provided developers and public beta testers with the release candidate version of iOS 26.1, which means Apple will likely roll out the update to all compatible...
maxresdefault

Apple TV 4K Could Still Launch Before 2025 Ends: All the Rumored Features

Monday October 27, 2025 4:51 pm PDT by
Apple is designing an updated version of the Apple TV 4K, and rumors suggest that it could come out sometime in the next couple of months. We're not expecting a major overhaul with design changes, but even a simple chip upgrade will bring major improvements to Apple's set-top box. Subscribe to the MacRumors YouTube channel for more videos. We've rounded up all the latest Apple TV rumors. ...
iOS 26

Apple Seeds iOS 26.1, iPadOS 26.1, and macOS Tahoe 26.1 Release Candidates

Tuesday October 28, 2025 1:07 pm PDT by
Apple today provided developers and public beta testers with the release candidate versions of upcoming iOS 26.1, iPadOS 26.1, macOS Tahoe 26.1, tvOS 26.1, watchOS 26.1, and visionOS 26.1 updates for testing purposes. The RCs betas come a week after Apple released the fourth betas. The new betas can be downloaded from the Settings app on a compatible device by going to General > Software...
M6 MacBook Pro Feature 1

M6 MacBook Pro: Release Date, Pricing, and What to Expect

Monday October 27, 2025 9:15 am PDT by
Apple this month refreshed the 14-inch MacBook Pro base model with its new M5 chip, and higher-end 14-inch and 16-inch MacBook Pro models with M5 Pro and M5 Max chips are expected to follow in early 2026. However, these machines will represent the final update to the current design, with Apple reportedly developing a completely new version of the MacBook Pro packed with next-generation hardware...
iPhone 17 Pro Cosmic Orange

8 Reasons to Wait for Next Year's iPhone 18 Pro

Thursday October 30, 2025 4:42 am PDT by
Apple's iPhone development roadmap runs several years into the future and the company is continually working with suppliers on several successive iPhone models at the same time, which is why we often get rumored features months ahead of launch. The iPhone 18 series is no different, and we already have a good idea of what to expect for the iPhone 18 Pro and iPhone 18 Pro Max. One thing worth...
macos tahoe

Here Are Apple's Release Notes for macOS Tahoe 26.1

Tuesday October 28, 2025 1:21 pm PDT by
Apple today provided developers and public beta testers with the release candidate version of macOS Tahoe 26.1, which means the update will likely see a public launch next week. The release candidate includes notes on what's in the update, so we have a full picture of the new features that Apple has included. macOS Tahoe 26.1 adds AutoMix support over AirPlay, improved FaceTime audio...
ipad mini 7 feature blue

OLED iPad Mini: Release Date, Pricing, and What to Expect

Wednesday October 29, 2025 7:13 am PDT by
Rumors are stoking excitement for the next-generation iPad mini that Apple is reportedly close to launching. So what should we expect from the successor to the iPad mini 7 that Apple released over a year ago? Read on to find out. Processor and Performance Apple is working on a next-generation version of the iPad mini (codename J510/J511) that features the A19 Pro chip, according to...
iPhone Car Key Kia

Another Vehicle Brand Gaining iPhone Car Keys Support

Tuesday October 28, 2025 5:27 am PDT by
Apple is preparing to bring support for its digital car key feature to Jetour vehicles, according to evidence uncovered on Apple's backend by MacRumors contributor Aaron Perris. Introduced in 2022, Car Keys allows an iPhone or Apple Watch to unlock a vehicle through the Wallet app. A digital version of a car key is stored in Wallet, and unlocking can be done by holding an Apple Watch or...