Problems Logging into Google Account in Apple Mail for Mac, After macOS 10.4.4 Update

Update: This issue has been fixed.

I updated my iMac to macOS 10.4.4 yesterday. This morning, when I went into my home office to work, I found that I needed to log into my Google account (I have my personal domain hosted on a Gsuite account) in order to get email.

Email

I clicked Open Safari, and Safari opened a private browsing window with a login page for Google. I entered my email address and password, then a one-time code, and it bounced me back to Mail, but all I saw was this:

Login

Something wasn’t sending the appropriate token back to Mail to allow the login. (I later tried creating an app-specific password for Mail on Google, but that was refused; it looked like the login it was requesting was not specific to Mail, but to the Google account in general.)

This was only happening on my iMac, which I had updated to macOS 10.4.4; not my MacBook Pro which hadn’t been updated, nor my iPhone. I called AppleCare, and they had me create a new user account on the iMac, where the same thing happened, confirming that the problem has something to do with this Mac, rather than my user account.

One thing that surprises me is this authentication procedure via Safari. In the past, I’m sure I entered my Google password in Mail, or in the Internet Accounts pane of System Preferences, and this Apple support document shows that you enter your password in Mail. So I’m not sure if this new process is causing the problem, or, as the Apple Care senior support person said, it has something to do with a certificate.

This is, of course, quite problematic. If you rely on email for your work, and can’t get your email, you are hindered. I can get the email on my other devices, or I can use the Gmail web interface, so I’m not totally locked out, but still; I manage my email in the Mail app, and don’t like using the web.

This sort of issue raises the question of whether it’s really safe to use an email system that does not work with standard username/password authentication. For some reason, the login requires transiting via a web browser, which means there is a weak link that can break.

In any case, I’m throwing this out in case anyone else has this problem. The Apple Care technician said that he was sending this to engineering as a high-priority issue, and doesn’t think that a macOS update would be required, that he thinks it’s most likely a certificate that may simply need to be updated. I’ll post more info when I get it.

Update: There’s an Apple forum thread about this issue, so it’s clearly a problem affecting a lot of people. Some users are reporting that this was a bug in the beta version of macOS 10.4.4, which was duly reported by many testers. If so, Apple really messed up, because so many people use Google for their email.

Some users are able to get their accounts to work by deleting the existing Google account, then re-creating it as an IMAP account, but this means that it isn’t recognized as a full Google account, which is problematic for those who use Google for calendars and other services.

The Best Mac Cleanup Tips for Digital Spring Cleaning

Spring is in the air. You can tell because the birds are starting to chirp, the days are getting longer, and you’ve set your clock ahead.

Whenever spring comes, something deep inside us prods us to clean things out. Our home, our garage, our basementÂ… so why not our Macs? We accumulate clutter in the colder, darker months, and with more light and warmer weather, it’s a good time to take stock of things and decide what you need to keep, and what you can toss.

In this article, I present a roundup of the best Mac cleanup tips for spring cleaning your Mac. This is especially important if you have a Mac with an SSD as space is more limited than a hard drive. Some of these tips are simple, some take a bit more time, but they’ll all help you tidy up your computer.

Read the rest of the article on The Mac Security Blog.

Intego Mac Podcast, Episode 71: How to Securely Dispose of Hard Drives

A Messages prank, Google getting caught with a hidden mic, and password managers have flaws. And we discuss destroying hard drives creatively.

Check out the latest episode of The Intego Mac Podcast, which I co-host with Josh Long. We talk about Macs and iOS devices, and how to keep them secure.

Intego Mac Podcast, Episode 69: Why Doesn’t Apple Have a Bug Bounty Program?

We discuss the Face Time bug that we mention in the last episode, and why Apple hadn’t updated it. But Apple released the update a few hours after we recorded this. But this raises the question of why Apple doesn’t have a bug bounty program. We also discuss a Keychain vulnerability on the Mac, the removal of the Do Not Track feature from Safari, and more.

Check out the latest episode of The Intego Mac Podcast, which I co-host with Josh Long. We talk about Macs and iOS devices, and how to keep them secure.

Intego Mac Podcast, Episode 67: FaceTime, Facebook, Google, Shortcuts, Steganography, and More

Apple had a mean FaceTime bug; then they slapped down Facebook, and Google, for some underhanded app distribution. There are security risks using iOS Shortcuts, and there’s new malware using steganography.

Check out the latest episode of The Intego Mac Podcast, which I co-host with Josh Long. We talk about Macs and iOS devices, and how to keep them secure.

Intego Mac Podcast, Episode 67: The Biggest Data Breach Ever; Is Your Data Included?

Google is blocking ad blockers, but not their own ads. Apple has released a slew of updates. And the biggest data breach ever has been discovered, with 2.7 billion records. Is your data included?

Check out the latest episode of The Intego Mac Podcast, which I co-host with Josh Long. We talk about Macs and iOS devices, and how to keep them secure.

Intego Mac Podcast, Episode 66: Routers, Tweets, Bugs, and More

This week we focus on a wide range of security news. From router vulnerabilities to tweets storing precise location data; from $2 million bug bounties to Face ID issues; and lots more.

Check out the latest episode of The Intego Mac Podcast, which I co-host with Josh Long. We talk about Macs and iOS devices, and how to keep them secure.

It’s the Ecosystem, Stupid*

(*Note: the title of this article is a riff on a statement made by Bill Clinton’s campaign manager during the 1992 presidential race: “It’s the economy, stupid.”)

We saw recently how Apple’s profit warning caused the company’s stock to tank. This is because the iPhone, whose sales are down, represents about 60% of the company’s revenue, and any disruption to that leading product has a strong effect on the bottom line. But at the same time, Apple’s services revenue is increasing, as Apple is morphing from a hardware company to a services company.

Apple is a lot more than just the iPhone; its products represent an ecosystem. In a recent interview with Jim Cramer on CNBC, Tim Cook said that the “virtuous ecosystem is probably under-appreciated,” and that “the ecosystem has never been stronger.”

Read the rest of the article on The Mac Security Blog.

Intego Mac Podcast, Episode 65: It’s the Ecosystem, Stupid

We discuss Apple’s trolling of other companies at the Consumer Electronics show this week, a delivery tracking app that sends and receives data in a strange way, and we then look at how Apple’s ecosystem may be “under-appreciated,” according to Tim Cook.

Check out the latest episode of The Intego Mac Podcast, which I co-host with Josh Long. We talk about Macs and iOS devices, and how to keep them secure.

New Year’s Resolutions to Check that Your Mac and iOS Devices Are Secure

Everyone knows that New Year’s resolutions don’t always stick. You may decide to join a gym or start a diet, and by February, you’ve slipped from your goal. But there are some New Year’s resolutions that you can use to check the security and your Mac and iOS devices. Here’s a selection of simple things you can do to make sure your devices are as secure as possible. (Listen to episode 64 of the Intego Mac Podcast where I discuss these and other tips with my co-host Josh Long.)

Read the rest of the article on The Mac Security Blog.