Mojave 10.14.4 fails to Authenticate Gmail account

Has anyone been in direct contact with Apple Support on this issue? After about a week of frustration with the problem I bitched loudly at them on Twitter, and they set up a phone consultation for me. Weirdly... and I have absolutely no explanation for this... the day before the appointment Gmail mysteriously started working again. So in the end I cancelled the call.

Still, it seems they do respond to being called in public, while they are notably silent on this forum. Since I didn't have to follow through, I have no way of knowing if they could have solved the problem, but it does seem like a worthwhile strategy to explore for folks still wrestling with the issue.

Note of thanks for your fix. I'm up and running with Spark, configured it and immediately it downloaded from the gmail server. Hope this will help others put an end to the aggravation of the past weeks.

Similar problem here only I can't SEND mail from Mac mail on my iMac. This is not a fix (but interesting) I delete the /var/db/crls/ folder (empty trash and restart) and I can send mail for maybe an hour then it goes back to its naughty self. Until this is fixed, I'm sending mail through iCloud web site which works fine.

Hope it gets fixed soon.

iMac (2017) 10.14.4

Char

That hasn't happened to me. It still works. This isn't a global issue with the operating system update... not everyone that has a gmail account is having this issue.

Removing all accounts and re-adding resets something to allow it to work.

I deleted my gmail account on my Mac and was unable to create it again. But I was able to use gmail on my iPhone so I was content to wait it out until they fixed it, which it seems they have because suddenly my gmail account reappeared on my Mac.

Apple, in my experience doesn't admit to bugs. They fix them and never communicate one way or the other. Amazing for such a successful business.

Unfortunately it is not working. Still the same issue. It’s fine for awhile but when it’s inactive all the gmail acts go offline and mail stops coming in. Ugh! This has to be some sort of security bug. I have dumped and re-installed all my Gmail acts and still no dice.

Also wanted to add that if you create a new gmail account... it sets up with no problem. The old gmail account that didn't work previously could be added under a new user account created on the mac.

"Also wanted to add that if you create a new gmail account... it sets up with no problem. The old gmail account that didn't work previously could be added under a new user account created on the mac. "

Thank you. I appreciate this and all the other advice. FWIW, I tried that as well as all the other suggestions. I've also rebooted, safe-rebooted, zapped the NVRAM, used ONyX to clean out every cache, rebuild the mail database, run the daily/weekly/monthly clean-up routines, etc. I've gone to my Google accounts and tried to find anything in those settings that would work. I tried the "use less secure applications" although I'm not happy about doing so. None worked for me, although I have been leery to mess around with contents that are deep inside the ~/library folder as I don't want to cause more problems than I solve. Maybe there's a solution there, but it shouldn't be up to me to do that, so I'm putting in a bug-report at the Apple site every day until this is resolved between Apple and Google. Good luck to all and congratulations to those who have solved their problems. Wish I were in your ranks.

You've tried it all @macsavvyflorida! It's pretty pathetic that something as simple as email can get screwed up by Apple and that there has to be 42 pages of comments, work arounds, time wasting and still no reply or fix from Apple. I too am still dealing with this issue but I finally gave up and just loaded an older version of mail that works just fine from my time machine backup... the fact the older version works and the new version doesn't (shrugs). Hoping this will worked out at some point in time!

@macsavvyflorida, I don't think this should require everyone to set up a new user in order to get the mail to work, as transferring everything over, setting everything up fresh takes time. It's one thing if one person has the issue, sure, there could be something wrong with their user account, but for MANY, that signals a bug in Mojave, and the way to address this is for Apple to acknowledge and promise a fix soon.

Thank you, @krasow. Speaking only for me, I did try the suggestion of Lazyants on 4/2 as well as a suggestion to delete everything Google or gmail related in Keychain. Unfortunately, for me, neither of those worked. I hope others have better luck.

From what I've read, this definitely appears to be an Apple problem and it's really annoying. I've wasted so much time trying various fixes I've read about online but to no avail, and I've also missed important emails on my Macbook. I've tried deleting and resetting my gmail accounts but then had to change passwords for fear of allowing a third party app to access my emails. Come on Apple, how can a problem like this get through and why is it not being sorted out immediately?

It's not just happening with Apple Mail. I switched to Outlook 2019 (latest version 16.24) and it's even worse than Apple Mail. I have 6 G Suite accounts that randomly fail to authenticate. Clicking on the little squiggle connects and then others go offline. At any given moment I will have 3 to 5 of 6 accounts offline.

In a previous post I mentioned the problem is even worse using the latest version of Outlook 2019. However, I deleted all the accounts from Outlook and added them back as IMAP accounts and so far, so good. It's been about an hour. I used imap.googlemail.com & smtp.googlemail.com as the servers.

Outlook actually worked fine for me when this problem first started, while Mail wasn't. For whatever reason- my Mail is working with Gmail now, but I know it isn't resolved for a lot of other people. Outlook doesn't use Apple's authentication mechanism for Google, so this points to it being just as much a Google (and Microsoft in the case of Outlook) problem as an Apple problem.

Unfortunately 10.14.4 came out at the same time Google was killing Google+ and making security/login changes (pushing hard on MFA). Google constantly makes changes and doesn't give anyone (like Apple or Microsoft) any kind of a heads-up. Keep in mind they only really support Google services on browser (primarily Chrome), ChromeOS, and Android. Everyone else has to figure things out as they go.

There is also no love lost between Apple and Google- they are competitors. It is in both company's best interest to work this out, but neither of them are likely to go public with it or really acknowledge a problem. It will be "quietly" fixed over time.

For most SMBs and individuals- Gmail IS email. Apple's iCloud mail isn't a good option at all, and Microsoft's products are overprices and even more difficult to manage. Hopefully this will get resolved soon.