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Gmail Authentication Error In Mac Mail SOLVED

2015 July 14
tags: Apple, Effective Email, Email, Gmail, Mac, MacBook Pro, Mail, Tuesday Tips, Two Factor Authentication
by Andrew   

effective emailAfter having a couple of email accounts fail to connect to Gmail due to an unspecified error, I spent a couple of fruitless hours attempting to troubleshoot the problem. I even re-created the accounts in Mail on my MacBook to see if some artifact within the existing account setup was causing the problem. Unfortunately, it didn’t work.

So, I spent another hour scouring Google’s search results for a solution, and despite reading quite a few articles and posts about how Gmail and Mac Mail ought to work together, none were recent enough to address this new problem that only manifested itself on OS X Mavericks. It may now be appearing on earlier versions of the OS, but I don’t have any machines running earlier versions, so I can’t tell.

Multiple posts have suggested adding the passwords in multiple places for both IMAP and SMTP, including in the Accounts setup within Mac under Mail > Accounts in the Mail app. Those posts were old enough that they didn’t acknowledge that two-factor authentication is theoretically functional within Mail. I say theoretically, because when it doesn’t work, it doesn’t work. And neither Google nor Apple have identified why anywhere I can find, and Mail specifies no useful error message.

The Solution

Fortunately, I decided to ignore the enter-the-passwords-in-three-locations advice and access the account setup advanced features directly through Mail > Preferences in the Mail app.  This method avoids Mail’s attempt to access the Gmail two-factor authentication and allows you to enter app-specific passwords directly.  You will need two app-specific passwords for each account.  Yes, two.  It’s ridiculous, but that’s how it is for now.

So, here are the steps that worked in under five minutes total:

  1. Open Mail > Preferences in Mail and navigate to the account you want to fix.
  2. Open a web browser and log into the same Gmail account as the one you want to fix in Mail, and go to My Account, then app-specific passwords.
  3. Create an app-specific password for SMTP.  Call it whatever you want, because Gmail doesn’t care; just make it something you will recognize later when you check the app-specific passwords list again.
  4. Switch back to Mail and go to the Advanced tab for the account you want to fix.  Add the app-specific password and navigate back to the main settings screen for the account.
  5. Switch to Gmail and create a second app-specific password.
  6. Switch back to Mail and enter the new app-specific password in the main password field.
  7. Navigate to another account or close the Preferences pane to save the changes.
  8. Wait a few seconds and enjoy the stable connections that no longer ask for passwords that don’t get accepted.

Take care, and enjoy life,

Andrew

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