Mojave 10.14.4 fails to Authenticate Gmail account

I've actually managed to fix the issue by setting up a local proxy that fixes the authentication request URL, as posted earlier:

https://discussions.apple.com/thread/250259379?answerId=250498073022#250498073022

Problem is, this solution will scare and confuse your average Mac user. Disgraceful.

to Grant-Y and others experiencing a personal Gmail account going offline automatically after update to 10.14.4 and successful authentication. Our issue may be connected to the OP's, but is not GSuite and not about getting caught in an authentication loop. Therefore, I started another thread to keep this issue more specific to our issue. Please see: https://discussions.apple.com/thread/250281627 so we may troubleshoot this specific Gmail issue. Thx

There must be 2 positive solutions to fix.

• That overwrites the response that Google’s servers are issuing using Charles would fix Authentication issue on Mac. You can see the specific steps with screenshots from here.
• use imap.googlemail.com and smtp.googlemail.com for your new configuration attempt

See yana131 post as per below. I don't use the gmail account calendar so can't confirm that it fixes any problem with the calendar.

yana131

User level:

Level 1

(4 points)

Apr 23, 2019 7:05 PM in response to Ken Graham

Hi,

i bring Apple mail working again. Is a Google GsSuite Account, thats ends not to gmail.com.

I Have 2 accounts one with 2FA one without. Only want mail functionality back first.

First, have same issues, can´t login, Safari opens ... endless loop and not online.

What i did.

1. Delete google Accounts in system Preferences -> Internet Accounts
2. Open Mail
3. Add Account
4. Choose other
5. Enter mail Adress / Username = full mail address / mail.gmail.com / smtp.gmail.com
6. Password A) Create one for 2FA in you Google Account for Mail
7. Password B) just choose the normal one

Update, also tested with my private @gmail.com -> works to

please try.

I bring my Private google Account back to live as Standard Gmail Account with Calendar and Notes...

i did 2 Steps to try, so i don´t know what it was in detail, please try

1. System Preferences -> Internet Accounts -> Google Account
2. Safari Opens
3. copy adress, leave window open
4. open new safari window cmd+n
5. paste adress
6. try to complete
7. for me, an error occours - can´t finish

1. back to original safari window
2. right click on top bar, change setting content blocker
3. complete with mail and password
4. account installation incl. mail and calendar finish as normal

so, can try content blocker settings first... but i can´t validate now

C.

I had the same message this morning, but I got the google accounts registered. Here is how I did it:

• In the "Mail" program go to "Mail/Accounts..."
• Click on the respective Google account (if you have multiple accounts you will have to do that for each one).
• A browser window opened. Provide your log-in information (username & password).
• A permission page appears > Accept.
• Instantly I got an e-mail alert, saying that I had a new sign-in.

After these steps for all of my google accounts I was able to download all of my e-mails.

Adding my experience too…

I have three Google accounts—all G Suite accounts—configured on two Macs: a 2011 iMac running High Sierra, and an early-2015 MacBook Pro running Mojave.

After upgrading to 10.14.4 on the 2015 MacBook Pro, I got the "Google Password Required" notifications for all three Google accounts.

1. Authentication using Single Sign On, Shibboleth, the URL indicates SAML2, and we use Duo's Two-Factor Authentication. This one works after I authenticated, and I can use this account across Calendar, Mail, etc.
2. Authentication using Single Sign On, ADFS, and the URL indicated SAML. After I authenticate and allow macOS to use my account, I get the same error you're all getting.
3. Authentication using Google with 2FA. After I authenticate and allow macOS to use my account, I get the same error you're all getting.

I only experience this problem with the 2015 MacBook Pro running 10.14.4, and I can use my accounts on the older iMac running 10.13.6.

Steps I tried:

1. Removed account from all my computers and re-added the account to both computers. Works on the older iMac (10.13.6) but not on the MacBook Pro (10.14.4).
2. Deleted Keychain entries for anything related to Google.
3. Turned off content blockers in the Private Window.
4. Disabled 1Blocker
5. Cleared cookies from Safari.
6. Turned off "Prevent Cross-Site Tracking" in Safari.
7. In the Google Security settings, I removed access for "Mac OS" to access my Google account. But after you authenticate, it get access again, and it still fails.

The weird thing is that I am able to authenticate to ONE Google account but not the OTHER TWO.

I'm having the same problem that most people are reporting on this thread -- one of my G Suite accounts is stuck in the endless authentication loop, and another one is fine.

I only use contacts on my Mac for "endless loop" account, so here's a temporary workaround that's working for me:

• Delete the Google account entry for it in System Preferences
• Re-add it as a CardDAV account. Choose manual configuration. The server address is google.com and the username is your G Suite email address. I use two factor authentication for my G Suite account, so I had to generate an app password to use in the password field here; if you don't use two factor auth, your plain old G Suite password should work.

After that, contact syncing works for me without the endless prompts.

While I only care about contacts, I suspect that you could repeat this process adding an IMAP and a CalDAV account to get access to Mail and Calendar as well.

Hopefully Apple fixes this issue soon so that we can go back to using a single, "standard" Google account.

The iPhone issue can be solved by following this steps.

• Delete current account
• Create new one by selecting Exchange instead of Gmail
• Server should be m.google.com
• An application password should be used from your G-Suite account web interface in Security submenu

This is a rather powerful solution that works only for G-Suite accounts (not free Gmail).

Of course, this is not the cleanest solution but can help awaiting for a fix from Apple. Here is the link to Google's explanation : https://support.google.com/a/users/answer/7649685?hl=en

Some follow-up to this...

I compared the failed account to my other Gmail accounts (that are connecting) and the only difference I can find is it was set up to "Allow Less Secure Access" (or something along those lines) enabled. I disabled that. I also removed access for all "Mac OS" instances so I could start fresh.

Unfortunately even after doing this- I'm seeing the exact same error.

So, steps I've taken to try to resolve:

• Closed Mail and deleted all cache files, emptying trash.
• Deleted account from Mac OS.
• Deleted access from Mac OS to Google Account in Google Account Management.
• Turned off "Less Secure Access" on Google Account in Google Account Management.
• Added Google Account back into Mac OS.
• Logged in to Google Account via Safari, as-prompted by Mac OS.
• Agreed to allow access to Google Account in Safari.
• Safari window closes, but account failed to complete set up.
• Getting "Enter the password for the account “(null)”." error again.

Me too.

I've been following this issue for a couple days now. Really frustrating.

Just to add to the data points, I have three accounts:

1. Personal account, very old, 2FA activated, works fine.
2. Personal account, very old, no 2FA, does not work.
3. GSuite account, very old, no 2FA, does not work.

So the issue is definitely not limited to GSuite accounts. Turning on 2FA did not help either.

Hi everyone,

I found a solution that worked for me, no need to delete accounts or set up new IMAP accounts. The trick that did it for me, on two different Macs for several different accounts, both @gmail.com and @mydomain.com (hosted by Google) accounts, was to go through the Internet Accounts pane in System Preferences and NOT through the Mail app itself.

Here are the steps I went through:

1. Open System Preferences and go to Internet Accounts.
2. Select the Gmail account that is refusing to log in.
3. Then, select one of the options that is not selected like Contacts or Calendars (I only use mail but not Contacts, Calendars, Notes so all these are not selected for me).
4. Then, I received a notification from macOS that I need to authenticate the account with the two options to 'Close' or to 'Continue'. Do NOT click continue just yet.
5. Quit System Preferences.
6. Then click 'Continue' on the Notification.
7. This will open System Preferences again (don't ask me why but if you don't close System Preferences before clicking 'Continue' it doesn't work) and a notification within the Internet Accounts pane pops up linking to Safari and the known Google Authentication process.
8. Go through the steps of entering your password and two-factor authentication etc. and then, sure enough, the account is logged in again also in Mail.

As stated above, this worked for several of my accounts on two different Macs and now all accounts are logged in again and work fine.

I really hope that this will work for others as well until the issue with the Mail app is fixed. Good luck!!!!!

AndreD's solution worked for me, as well, and I'm using a G-Suite account. The steps were slightly different, but it worked ... where nothing else did previously. My steps:

1. Uncheck all G-Suite syncing from the Internet Accounts preference pane.
2. Close System Preferences.
3. Open System Preferences > Internet Accounts, and choose Calendar for syncing.
4. Get a popup asking me to authenticate. Choices are "Cancel" and "Open Safari."
5. I chose "Open Safari" and went through all the authentication procedures I had previously.
6. Like magic, I'm in.

I don't know why this worked, and I don't know if all these steps are necessary. I simply (and desperately) tried to mirror AndreD's solution as closely as possible. I won't look a gift horse in the mouth, but I did want to validate that there's something here. Disclaimer, FWIW, I only sync my calendar, because our company policy doesn't allow me to use desktop clients for email. So your mileage may vary.

Here is the only workaround that worked for me. I had to add the Google account in Mail using the option "Other Mail Account..."

1. First you need to prepare your Google account by generating an app specific password https://support.google.com/accounts/answer/185833 and by enabling IMAP https://support.google.com/mail/answer/7126229
2. Then open Mail
3. In the menu choose "Add Account"
4. Choose "Other Mail Account..."
5. Use your email address and the app specific password you generated. And for the servers use the following:

outgoing: smtp.google.com

incoming: imap.google.com

Good luck