Google 2-step verification failing in 10.10.3 'Internet Accounts'

And, all of a sudden, mine's working beautifully right now. No configuration changes, have literally had the little exclamation mark sitting next to the account for days. This morning it's all going perfectly.

Something changed on the backend with Google perhaps?

Oops, the network I was on just sucked.

Similar issue here but mine is specifically with a Google (Apps) for Education account. We have SSO enabled (not sure if that matters though) After installing 10.10.3, the following behavior occurs:

When adding a new account, if I select the Gmail, a window pops up with what now looks like Google's normal web authentication sign-in page. I enter in my credentials and I get redirected to my school's shibboleth SSO. Even with the correct credentials I get that "failed to authenticate with Google" error.

I can get around this issue and still add an account by selecting the "Add Other Account" option. In this instance it by passes the SSO and I can use my Google Apps username and Google Apps password like prior to 10.10.3 to successfully add the account. The problem is, even after I am sending and receiving just fine, any time you go into System Prefs > Internet Accounts and click on the Google Apps account, it keeps trying to authenticate me via my SSO and gives the "failed to authenticate with Google" error when I put in the correct SSO credentials.

Are you guys that are having issues with 2-step, using regular Gmail.com accounts or are you also on Google (Apps) for Education/Work? For the ones with 2FA issues, have you tried adding the account as "Add Other" to see if your app specific password words there?

Yes - only for Google Apps, Gmail is okay.

Kind of the same issue here. I have two computers: an iMac and a MacBook Pro, and I use Keychain Sync. I have two gmail accounts: one is an old-google-apps email, and another one is a new-google-apps email. Both have 2FA enabled. I am able to successfully authenticate with both using System Preferences / Internet Accounts on my iMac, and everything works well. But when my accounts get synced via keychain sync to my MacBook Pro, it prompts me to re-enter the password for my new-google-apps account. When I do so, I'm able to sign in, then give the permissions, and after the permissions dialog closes, I get "failed to authenticate with Google" error. I tried deleting the problematic account, and tried creating it on a MacBook Pro first, and again, it works fine there, but when the account gets synced to my iMac - same problem occurs. The problem doesn't occur with my old-google-apps account.

Let's hope so 😉 Mine appears to be working, but there's still a little squiggle next to my inbox and I get repeated requests for a password for my secondary gmail address...

I have the same issue since updating to 10.10.3!! This is terrible Apple. I can't send or receive messages. PLEASE FIX IT ASAP!

That's good to hear Chassa.

Mine's back broken again after working great for a couple of days. Hopefully they can squash whatever the bug is because once it gets a connection it's working very well.

I am new to Mac OS. I am beside myself. Basically Apple has rendered my new MacPro useless for work. I took a risk by moving from Windows and I end up with this. Nice learning experience. Very Very Upset!!! The problem with Apple is there is no work around. All my windows experience with their blunders had a workaround. I basically have a $2000.00 aluminum brick right now.

Ok, I had this problem as well and was ready to pull my hair out. Here is what finally worked for me…

1. Generate the app password for Apple Mail in your Google account settings.
2. Open Mail, select Preferences>Accounts>Select your Google Account
3. Go to Outgoing Mail Server (SMTP) and from the pull-down menu, select Edit SMTP Server List
4. Select your gmail account in the Server list then click on the Advanced tab
5. Change the Port to 25
6. Delete the current password and enter the password you generated from your Google account and click OK
7. When you are back to your Account Information, delete the current password then enter the password you generated from your Google Account
8. Click Save or Apply when Prompted
9. Quit Mail and re-launch.

Those steps worked for me. When I re-launched Mail, it took about 2 minutes for my sent mail to leave my outbox, but after the initial mail sent everything was back to normal. Also note when I went back and looked at the server settings, the Port had changed back to 587 but everything is still working fine. Good luck everyone!

Cheri

🙂

Hi!

Since the issue is only for Google apps mail accounts (not Gmail). Here how to do it:

1. Make sure you updated to the latest OS version.

2. Make sure you enable 2 step verification in Google account settings.

3. Lastly, add your password in the advanced Smtp setting.

Take note:

1. no need for generating an app password since 10.10.3 is designed to make 2 step verification easy...

2. No need to change ports

This is not true. I had the issue for my regular Gmail account. The 2 step verification on my Mac would not work, and I had to add my app specific password in Mail.app.

good to hear, Chassa, thanks. Hope they manage to fix this soon.

Of course it's true. Now Gmail accounts all you do is nothing.

Nothing meaning... don't activate 2 steps verification and also don't make an app specific password.

Just simply remove and re-add the account in the "internet accounts"