Failed to authenticate with Google...?

Since upgrading to OS X 10.10.3 I have been receiving repeated prompts that my Google password is required in Internet Accounts. On entering the password I am prompted to give OS X permission to work with my account. This is always followed by an error:


User uploaded file


Is anyone else getting this? Any suggestions? It looks like a possible Keychain issue, or is Google not allowing OS X to authenticate? I considered enabling less secure apps in Google temporarily to allow authentication, but I tried this and no joy... I'm on a 13" mid 2013 MacBook Air.

MacBook Air (13-inch Mid 2013), OS X Yosemite (10.10.3)

Posted on Apr 16, 2015 12:14 AM

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57 replies

Jun 26, 2015 12:41 PM in response to catkato

WARNING Before you delete your email account understand this:

I DID this and things got even worse. I couldn't create a new Googlemail account because of the same "failed to authenticate" problem.

Spent two hours with Applecare. the fix was to go in from Safe mode and create the account in there, log out, and then go in regular. and it worked, although even Applecare doesn't know why.

The advisor told me that you should never delete an email account because you don't know if you'll be able to get it back. And from now on I won't.

Jun 26, 2015 9:20 PM in response to jakela

I had the same problem with "Authentication failed" and "Failed to authenticate with Google" when I tried to log onto Google over and over again. I bought my iMac in 2009 and upgraded to Yosemite several months ago. I think I've found and solved the problem. I've had no requests to log onto Google since I did this.


  • On Google homepage, click blue icon in top right corner and ---> My Account
  • In My Account ---> Personal info & privacy ---> Account Overview
  • In Personal info & Privacy ---> Account overview ---> View Dashboard
  • In Dashboard ---> Account ---> Connected applications and sites
  • Here lies the problem. I found that, even though I have run Yosemite for many months, both IOS and OS X were listed here, WITH IOS INDICATED AS THE CURRENT SYSTEM. I deleted IOS, leaving OS X as my operating system.

Sep 16, 2015 12:50 PM in response to IcyMacl

I was getting the failed login in Internet Accounts after enabling 2-step authentication for my Google Apps account. After poking at this for far too long and trying the suggestions in this thread that were available to me (I'm not an admin for my Google Apps domain) I think I finally resolved this by adding an app password to _both_ the incoming and SMTP password fields in Mac Mail.


Mail > Preferences > Accounts: use app password in the Password field of "Incoming Mail Server"

Outgoing Mail Server > Edit SMTP Server List > Advanced: use app password

I had also been playing with the suggested port numbers of the SMTP server (25, 465, 587), and 587 was the one being used when it finally worked...so I'm leaving it there.

Hope this helps someone!

Dec 6, 2015 2:12 AM in response to IcyMacl

Hi -


This happened to me. I discovered that I had 2 Google mail's on my computer - I deleted the 'gmail.com' and kept the 'googlemail.com' . I then sent myself 2 emails - one to gmail and one to googlemail addresses - they both appeared in googlemail... so my suggestion would be to check your mac settings and if you have two emails - delete the one that keeps asking for authentication - do not re-add it (I did that previously and it didn't work)... just keep the one email address for google. it works !


Scarlet

Nov 17, 2016 2:15 PM in response to IcyMacl

I just got this when I tried setting up my new iMac. I tried the following without success:

  • Setting up my account in mail and System Preferences multiple times
  • Deleting entries from Keychain.
  • Deleting the account and setting it up again.
  • Turning on 'less secure apps' in gmail preferences

Finally went to my account settings from within Gmail -> Sign in & Security -> Connected Apps & Sites -> Manage Apps


OS X was listed as a connected app. I deleted that and then went back to add the account from OS X System Preferences and it worked perfectly. Hope this helps someone.

Nov 20, 2016 1:15 PM in response to IcyMacl

TLDR: Don't block "partner.googleadservices.com"..


I finally found "my answer" (as it seems to be different for everyone..) I use a custom hosts file to try to cut down on the ad/javascript crap that today's web spews at us all (*) It turned out to be that blocking "partner.googleadservices.com" seems to cause the problem. Why, who knows?


(*) As long as the FDA is going to treat the Internet under Title 2 or whatever as if it were a *railroad* - they should set up a tax to pay for sites to be used and get rid of all the ads. Only problem would be what seems to happen with ALL taxes - they become slush funds for politicians.. So, never mind.)

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Failed to authenticate with Google...?

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