The TL;DR on Apple’s macOS Mojave 10.14.4 Gmail/G-Suite Issue: It’s Fixed

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| Analysis

Earlier this week many folks began experiencing an issue where macOS Mojave 10.14.4 could not properly log in to some Gmail-based accounts, mostly those using G-Suite for custom domains. The good news is that, as of late last night, this problem appears to have been eradicated.

Our best guess is that this was a Google-originated problem, at least this week. Here’s the timeline that leads us to this conclusion:

  • January, 2019 – Early in the 10.14.4 betas, developers and other beta testers reported having this exact issue. It then went away, though it’s hard to tell if Apple took any specific action to fix it.
  • Monday, March 25, 2019 – macOS Mojave 10.14.4 was released. Anyone updating on this day had no issues.
  • Tuesday, March 26, 2019 – Folks began having the aforementioned authentication loop/fail issue and were unable to retrieve mail with macOS Mail.app from some Gmail accounts. A few also reported issues with iOS, though reports on that were spotty, at best.
  • Also on Tuesday, March 26, 2019 – Google announced they rolled out some changes to G-Suite authentication. These primarily talk about changes to two-factor authentication while the bug affected folks with and without that, but the timing is too coincidental to ignore.
  • Tues-Friday, 3/26-3/29/2019 – The web blows up about the issue, folks are scrambling trying to sort out various solutions and workarounds. One of these fixes involved using Charles, a piece of proxy software, to intentionally play a “man-in-the-middle attack” on your Mac, inserting itself as Google’s authentication servers, passing back a piece of information that was missing from Google’s own response.
  • Late-night, Friday, 3/29/2019 – The problem simply goes away, seemingly without Apple having made any changes to macOS on anyone’s Macs.

Adding together the timing of when the issue started, Google’s G-Suite authentication announcement, the method by which the “Charles workaround” worked, and the timing of the solution, our interpretation is that Google fixed the issue on their servers last night and now all seems to be well for everyone from whom we’ve heard. And ourselves. Our long, international nightmare is now over.

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jotaeh
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jotaeh

Seems to be fixed after the OS X 10.14.5 update. However when you first start Mail after the update, you’ll have the little squigglies that indicate you’re offline. Clicking on them will bring the account online (you have to click on each one in the accounts pane).

It’s been 4 or 5 hours since updating and so far so good.

Graham McKay
Member
Graham McKay
jotaeh
Member
jotaeh

April 26 and definitely NOT fixed. Temporarily switched to Spark, but that has issues of its own. Would prefer a working Apple Mail.

Member
chuhaitime

Forwarding to another non-gmail account

juanantonio
Member
juanantonio

The bug is definitely NOT fixed. Still having this issue as of April 8th. Does anyone know a temporary workaround?

Member
Mark Lierley

Not so much fixed. Issue is still happening as of 4/8

Wylienet
Member
Wylienet

This just worked for me. I’ve been having the same problems over the last week using my Gmail accounts in Apple Mail. However, I also noticed yesterday that a piece of malware (Datatransportation) kept popping up and freezing my screen. I ran Malwarebytes to try and remove it, restarted my MacBook and hey presto, my Gmail in Apple Mail is now working again. Not sure if it’s a coincidence or not, but perhaps the Gmail issue was actually a malware issue?

Member
Sara Nichols

Still having this issue. The only temporary fix is quitting mail, then opening back up. It works for awhile, then I get the offline symbols again. It’s not asking for log in, just giving the symbol. Forcing them to go online also doesn’t work. Hope they fully fix this soon.

kalibrooke
Member
kalibrooke

Same—issue still occurs for me. I haven’t had any success by clicking the offline symbol for all accounts, but if I click them individually, it forces them online one-by-one. However, I have to do this constantly throughout the day.

Member
Monique Buchanan

Incidentally, this issue is also causing problems with my Apple Calendar accounts, since I use Google for my calendar.

Member
Monique Buchanan

 Late-night, Friday, 3/29/2019 – The problem simply goes away, seemingly without Apple having made any changes to macOS on anyone’s Macs.Adding together the timing of when the issue started, Google’s G-Suite authentication announcement, the method by which the “Charles workaround” worked, and the timing of the solution, our interpretation is that Google fixed the issue on their servers last night and now all seems to be well for everyone from whom we’ve heard. And ourselves. Our long, international nightmare is now over. No, for me this problem is not fixed and it is a nightmare. I have three gmail accounts and… Read more »

ASLReBecca
Member
ASLReBecca

I’m on a Mac, have never had this problem before, updated the system last night, and today I got the request to verify my account through Safari. So I did this and went back to Outlook. I cannot get Outlook to recognize my gmail account at all.

ASLReBecca
Member
ASLReBecca

I’m still shut out, so it’s not fixed everywhere. I cannot be the only one.

Member
chuhaitime

It might be better, but it’s not 100% fixed.  As of Sunday Match 31 at 6 pm, I am still getting random periodic Login Failed messages. If I click the message, it logs-in OK and stays that way for a few hours and then the log-in drops again.