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 19, 2017 10:01 AM in response to IcyMacl

I had the same problem. Try sending an email (using Apple Mail) from each of the email accounts synced with Apple Mail. If this is successful, then this post will not help.


If not, you'll see options corresponding to the smtp server lists. This is where my previous settings said "smtp.gmail.com". Instead select "www.google.com" or "www.gmail.com". Now, you should be able to send emails. Once this goes through, my iCal synced properly almost simultaneously.


Hope this helps.

Best,

Apr 24, 2015 4:05 PM in response to Eric Root

Google Support is useless. It just shows you how to change your password, but that is not the problem. You don't get to the "authentication failed" stage if you haven't entered your password correctly. It's something deeper than that. Most "fixes" posted on the Net are for Android devices, but this isn't a problem on my iPad or iPhone - only on my desktop iMac, and only since the last couple of updates of Yosemite.

Apr 26, 2015 9:47 AM in response to IcyMacl

I have the same problem- a notification appears saying 'Google Password required', so i follow the steps -continue -to a page titled Internet accounts, listing iCloud, and two google accounts. I have a separate gmail account, and a .mac, .me, .cloud account that are all aliases of my original mac.com account. It asks me to sign in to my gmail account, accepts my password, spins for bit, a mysterious page with some code appears for a milisecond, and then the 'authentication failed' appears. I am able to access my mail, and the internet, but the notification is annoying at best and worrisome. I too recently upgraded to OS X....

Apr 27, 2015 3:29 AM in response to SuZon.08

I had this when it was working before.


I checked the gmail address and it was different to my current address - so I just deleted the Google calendar entry and re-created it with the correct email address and it solved my problem. It was originally configured with googlemail.com and was working - now everything is converted to gmail.com the issue popped up during conversion I am guessing.


I'd be interested to know if this fixes anybody else.

Apr 27, 2015 4:03 PM in response to kevinfrompulborough

The thing is I don't use Google calendar or gmail. Of course I have a gmail address, but it seems to have the same password as all my other Google things. It's not a password issue, because it is very quick to reject a mistyped password - it's the next stage, the "accepting" stage where it all breaks down. I love this latest OS upgrade because start-up and opening most apps is so much quicker, but under the previous OS version it was only iCal that demanded a password, so I only got a notification when I looked at my calendar, but now it's for all Google things. I still wouldn't like to guess whether it's the OS or Google's bringing everything together that is causing the problem.

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Failed to authenticate with Google...?

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