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Mail still constantly asks for Gmail password

I have been unable to use Mail for over a year now due to the fact that no matter what I do it asks me for my Gmail password every two minutes. I thought I would give it a try after upgrading to Yosemite Beta and I see it is still the same situation. Hard to believe that after YEARS of this known issue there is still no fix. Mail is unusable in this state and it forces me to us ***whisper*** Outlook ***gag***.


At least on Mavericks I could use Google Chat in Messages but that functionality is broken now in Yosemite.


I have deleted every Google related item in my keychain, deleted and reinstalled the account, said really nice things to my mac and it still won't cooperate. Now when I try to add the account In Yosemite it will only connect with Contacts and Calendar and can't even make the connection with Mail, Messages or Notes.


Strange because my Google Drive sync works just fine!


Anyone know a solution for this or are we going to wait a few more years for this remain unfixed?


Any help you can provide would be great. I would love to use Mail someday!

Posted on Jun 19, 2014 5:46 AM

Reply
33 replies

Sep 26, 2014 1:07 AM in response to Csound1

I'm seeing exactly the same issue with Yosemite Beta 2 and Beta 3. I have 2-factor auth set up with Google.


iCal and Contacts sync works fine. The Mail sync works occasionally, but then starts to fail. If I reset the 2FA password and re-enter a new one, Mail works for a bit, then starts to fail again. 2FA works everywhere else except in Mail. Googling the issue shows that it's also been a consistent issue prior to the Yosemite beta. Would be really good if Apple just fixed this, as it now means I can't use Mail at all.

Sep 26, 2014 11:52 AM in response to admincn

Hi,


It does work.

User uploaded file

What I did find out from another thread is that it has to be Set at Google to be a "Less Secure" App despite it using SSL.


As has been said two step verification can seem to get in the way.


On the Google page for this.


Allowing less secure apps to access your account

Google may block sign in attempts from some apps or devices that do not use modern security standards. Since these apps and devices are easier to break into, blocking them helps keep your account safer.

Some examples of apps that do not support the latest security standards include:

  • The Mail app on your iPhone or iPad with iOS 6 or below
  • The Mail app on your Windows phone preceding the 8.1 release
  • Some Desktop mail clients like Microsoft Outlook and Mozilla Thunderbird


You need to start here https://www.google.com/settings/security/lesssecureapps?hl=en


(Messages is one that they deem a Less Secure app but what "security" they are using is not clear.)



User uploaded file

7:52 pm Friday; September 26, 2014


 iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

Sep 30, 2014 5:58 AM in response to Ralph-Johns-UK

You seem to be missing the point. I have 2-factor auth enabled on my Google account. Despite specifying a one-time Gmail password in Mail, I get an error when getting Gmail from Apple Mail.


You said "it [Apple Mail] has to be Set at Google to be a 'Less Secure' App despite it using SSL". You suggested following this link: https://www.google.com/settings/security/lesssecureapps?hl=en


If I follow that Link, Google displays this message: "This setting is not available for accounts with 2-Step Verification enabled. Such accounts require an application-specific password for less secure apps access."


So, the problem of Apple Mail failing to get email when 2-factor auth is enabled in Gmail clearly cannot be solved by switching Google to be a 'Less Secure' app.

Sep 30, 2014 12:38 PM in response to Ralph-Johns-UK

Hi,


I have an email response to this that is not visible to me here at the time of writing this post.


In the Original Post was this part:-


and can't even make the connection with Mail, Messages or Notes.


I wrote a reply with a pic to say that Messages did work but needed the Less Secure setting to be set.


You said the two did not work, which I thought you meant you could not have set no Two Step verification and have Less Secure setting (with a pic).


At not point have I mentioned the Mail App

I have also realised you are also not the Original Poster and have not mentioned Messages either.

It seems we have been talking at cross purposes.


As the Original Poster was suggesting a move to Outlook I was looking at the Quote from the Google page.


Two Step Verification only works if it is not being used to exclude certain connection from other "third party" apps of the Vendor who is using it.

At present I have not seen a good enough reason to move to Two Step Verification.



User uploaded file

8:38 pm Tuesday; September 30, 2014


 iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

Nov 18, 2014 4:23 AM in response to Ralph-Johns-UK

It's nice to try and help people but I regret the answer to the problem cannot be found on this page - or anywhere it seems. To be clear, my problem is:


Mac running OS X Yosemite. Google 2SA turned on and then my google account using Mail on my Mac will not accept the old password or an app password - it keeps asking for an app password. I revoke and regenerate and it doesn't accept it. There is an option to insist on verification on this computer and it doesn't matter if it is turned on or off.


Grahame

Nov 18, 2014 12:14 PM in response to Zoot42

Hi,


Mail uses SSL to try and Login to Google.

As SSL app Google deems this a "Less Secure app".


You need to turn Off two Step Verification as you also need to Enable the "Less Secure Apps" option on your Google Settings (the Less Secure app will not work when two Step Verification is On).





User uploaded file

8:14 pm Tuesday; November 18, 2014


 iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

Nov 18, 2014 3:03 PM in response to Ralph-Johns-UK

Hi Ralph


Did you read other people's responses to this? You can't do this. There is no option to do so when you have 2SA switched on. Repeating bad information is not helping. Now, if you think about what I have written there may, just may, be an answer. Frankly, the system was broken last time I tried (maybe a year ago) and is still broken so I can't be bothered right now. If I find a solution I'll post it. Thanks for trying to help, but repeating advice which is useless is not helping.

Nov 19, 2014 12:26 PM in response to Zoot42

Hi,


I did presume that 2SA was 2 Step Verification.


I have never set it at Google.

I also have the Less Secure option enabled.


Mail and Messages work.


I have read other posts where someone told me that if 2 Step Verification was "On" then there was no access to enabling Less Secure apps.


Mine is working. These are my Settings.


I hope you find a solution.



User uploaded file

8:26 pm Wednesday; November 19, 2014


 iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

Dec 24, 2014 8:58 AM in response to Zoot42

I too had just discovered this problem as I was using Two Step Verification. I found that my IMAP/POP3 was disabled on the gmail account.


I had disabled 2 Step Verification and allowed less secure apps and still was not seeing mail in my MAIL app. After going back to the basics I found this article,



https://support.google.com/mail/troubleshooter/1668960?hl=en#ts=1665018


After enabling the IMAP settings in GMAIL, I tried to add 2 Step Verification back and it worked. Hope it helps you!

Mar 10, 2015 3:57 AM in response to spinningstill

I too had same issues but today I got a popup window from Internet Account and it showed me the traditional Gmail Login to login using my master password than the App Password. The issue got resolved once I entered it. This came after I updated my MBP with the beta updates program which also gave me the Photos.app. I'm guessing you'll get this issue resolved in the next Apple update else try to backup your mbp and switch to beta updates like i have done.

Apr 11, 2015 10:14 AM in response to TheTimeTraveller

My experience was close to this, but not quite, so here's what worked for me just now:

  • OS X 10.10.2 (Yosemite)
  • Both Apple Mail and iCal had stopped syncing with one of my Google accounts (mail and calendar), as indicated not only by failure to sync (compared to updates visible on my iPhone) but also by the "~" icon
  • 2-Step Verification and app-specific passwords had previously been working fine on this Google Account, and never stopped working fine on my iPhone (iCal only, since I use Google's iPhone app for Gmail)
  • various suggestions had not fixed the problem, including
    • revoking the app-specific passwords and entering new ones
    • unchecking "Enable this Account" in Mail's Preferences > Accounts, then re-checking
    • hiding/showing the account in Mail and iCal
  • What did work was a combination of suggestions:
    1. Revoke all old app-specific passwords associated with the Google account and your Mac (you can leave the iPhone/iPad/etc ones alone)
    2. In Gmail settings (in a web browser, via the gear dropdown at upper right > Settings), go to the "Forwarding and POP/IMAP" tab, click the "Disable IMAP" radio button, and click the "Save Changes" button at the bottom.
    3. In System Preferences > Internet Accounts, delete the Gmail account entirely (and verify in Mail and iCal that it's gone).
    4. Reverse step #2 (click the "Enable IMAP" radio button and then "Save Changes")
    5. Generate a new app-specific password for the Google account. Realize that "app-specific password" is now a bit of an inaccurate term for Mac users on Yosemite (OS X 10.10), unlike in the past, because you now only have to generate one for your entire Mac, for use in System Preferences > Internet Accounts. In other words, you don't need to generate additional app-specific passwords for Mail or iCal as in the past. I suggest using the "Other [custom name]" dropdown option to help you remember this in the future, e.g., name the new password "Internet Accounts on my MacBook Air".
    6. Reverse step #3 (re-create the Google account in System Preferences > Internet Accounts using the new app-specific password from step #5, and check whichever boxes are appropriate (Mail, Contacts, Calendars, Messages, Notes; personally I only do Mail and Calendars).
    7. Verify in Mail and iCal that the accounts appear and are syncing OK. For me, initially iCal was working but Mail was not, until I remembered step #4 above.


Hope this is helpful, good luck!

Mail still constantly asks for Gmail password

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