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Gmail SMTP 2 Factor Authentication on OSX iMail

The following method has worked for me when it comes to sending emails via SMTP using Google Apps Account with Two Factor Authentication (2FA) enabled. I am sure this method can also be followed for regular Gmail Accounts.

On Your Google Accounts

  1. Revoke the Application Specific Password for iMail
  2. Create a New Application Specific Password for iMail

On Your Mac

  1. Go to Keychain Access and Delete
  2. On iMail Change the Outgoing Mail Server (SMTP) by selecting the Edit SMTP Server List and click the Advance tab
  3. Make sure the Username is your Email Address and the Password is the one you have generated on the above step.
  4. iMail will prompt for the SMTP server confirmation along with a prompt for a password, make sure to use the one which was generated on the above list.

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