Mojave 10.14.4 fails to Authenticate Gmail account

@alexnovelli

Go to System Preferences

Add account-> choose Caldav

Add your email address as login

Add an application password (so, not your regular one but an application generated one)

Put google.com as server

that should work

I got it!

1 - Open Calendar app and go to preferences > accounts

2 - Add Other CalDav Account

3 - Account Type: Advanced

4 - User and password Google account, of course

5 - Server address: www.google.com

6 - Server path: /calendar/dav/your-user@gmail.com/user/

7 - Port 443 + Use SSL

Just done!

This worked perfectly for me on both macOS and iOS 12.2. Removing the certificate shouldn't make it disappear. If it tries to re-authenticate and Charles is not running (with the certificate), then there could be a problem. I haven't seen it try to re-authenticate.

I was also able to get the Charles rewrite rule change to work, but with a slight variation.

For my GSuite account, the rewrite worked as described. No issues.

I also had an older personal account that had the same "fails to authenticate" issue, and for that I also had to add another rule to overwrite the response code to 200 (it was returning 404). Once BOTH rules were in place, I was able to add the once broken account.

Now all three Gmail account are working as expected.

Based on this, I'm thinking it could be more of a Google issue, exposed by changes made by Apple.

The native CalDav/IMAP approach worked for me in the interim until they fix this. Downside is you have to enable less secure apps, which you might not have the permissions to do. I was going to go down the Charles path, but this was just easier for me. Also sent feedback to Apple about the issue. At least there's some workarounds in the meantime-- Thanks to the folks that figured out the auth rewrite solutions. Much appreciated

I tried every work around posted and the ONLY one that worked for my Gsuite account was the Charles Rewrite. I had to repeat on my two Macs. Here is the process I followed. If this guy figured it out why can’t the Apple engineers fix it? https://forums.macrumors.com/threads/mac-mail-app-broken-for-some-gmail-users-in-macos-mojave-10-14-4.2175312/page-4#post-27232575

The solution that seems to have worked for me is the Charles bypass. See here: https://forums.macrumors.com/threads/mac-mail-app-broken-for-some-gmail-users-in-macos-mojave-10-14-4.2175312/page-4#post-27232575

Hopefully there is an official fix soon!

...same problem here, after going through the authentication for all of my various email accounts administrated through Google, only two will not properly authenticate, and both of them are affiliated with Univ. of SoCal.

I attempted to delete and recreate, which has worked in the past for troublesome accounts, but no dice with this Apple self-created foible.

I have a personal gmail account on two Macs with two-factor authentication. This worked on both and is mentioned earlier - but I could not find it to reference:

1) Open System Preferences->Internet Accounts

2) Click on Gmail Account. It immediately opens a dialog box with "Open Gmail in Safari". Click this.

3) Safari opens and prompts with your user name in the gmail login. Click Next

4) Safari gmail login asks for Password, type it in, then click Next

5) Safair gmail login asks for 2-factor key. Type it in and click Done.

6) Mail was already open and updated the Gmail mailbox instantly.

This worked for both Macs.

The direct link for the Charles rewrite is here from MacRumors user @Gannett. Follow the instructions carefully. Charles is a free download, runs for 30 days, and has a 30 minute timeout – some of us should buy or donate to thank him!

As best I can tell this process need only to be performed once per account to verify. Charles does not need to be running after that.

Also note that you need to repeat this process one by one for each G-Suite account by updating the email address in step 9 and then accessing the account in Apple Mail "Accounts". I had to select Contacts or Calendar and then click on another Account to trigger the Safari update window. 

Good luck ... YMMV

The Charles Rewrite also worked for me, after all other posted work arounds failed. I had to repeat on two Macs. However my iPhone and iPad were also not working with one of my two gmail accounts (one part of Gsuite) so I used a IPSW file and restored both of them back to the prior iOS version, which is still signed by Apple and won't upgrade to 12.4 until it is fixed. It may be the issue will need to finally be fixed by Google but it was Apple that released MacOS and iOS updates that were not working and did it knowingly and it was some change in the mail.app that broke things on both the Mac and iOS. Easy to blame the Apple engineers, but from my experience it was the marketing people who insisted to meet the schedule for Apple News+. Apple and Google are probably not in a hurry to fix, because they think it might reflect badly on the other one but I think Apple is getting the lion share of the blame here so Apple how about even acknowledging publicly there is an issue and a schedule for the fix?

Ken Graham’s solution does not work for me.

After entering my password, I do not go to the request about 2-factor authentication. Instead I get a prompt to enter my password in Safari—“Enter the password for the account “(null)”.

Hey all,

This happened with my university account too. The way I fixed it was to delete the account completely, retart, and then add it all over again. This should set it back up as a new account, completely ignoring any previous account.

Do this in system preferences and disable mail in this final setup section. Restart, then manually re-enable the mail. Hopefully this workaround might your accounts!

tl;dr Apple is aware of the G-Suite Gmail authentication problem and is working it but does not yet have a solution that works for everyone. 

I’ve had two phone sessions with a Mac Senior Advisor at Apple to help resolve my G-Suite Gmail authentication problem. Yesterday, after several attempts to resolve the issue that didn’t work, he went to the Engineering team to get advice on next steps and called me back today. Based on feedback from Engineering, he had me remove all of the keychain entries associated with my Gmail accounts then try authenticating my G-Suite Gmail account. Still didn’t work, same endless authentication loop. He confirmed that Apple has been getting many reports of this problem and is working it, but removing the Gmail keychain entries has worked for some people. He also confirmed most of the authentication issues are with G-Suite accounts, but not all. My guess is that some people who have a Gmail account and report the problem don’t know if it’s managed through G-Suite. The advisor said he would either get back to me with a proposed fix/work-around, if Engineering is able to come tip with one, or it will come out with the next Mojave update. So this may be awhile before it’s fixed. I will post any feedback I may get from the advisor.

Just spent 30 minutes on the phone with Apple Support with no fix. After speaking with a senior tech person the first agent told me that this was an issue with Gmail and I'd need to reach out to Google for a fix. She said they are aware of the problem with other users, but stopped short of offering any help.