I've liked what Google has done security wise lately.. I use 2 factor authentication and wanted to use my Gmail for FreeNAS outgoing mail.. Didn't realize email could still be used with Gmail SMTP+2-factor authentication.. I did the following to enable..
1. Ensure Gmail/Google is functional as you desire with your desired settings.
2. Ensure IMAP is enabled within Gmail Settings.. ?
3. Within the Google Accounts Dashboard.. Access the "Manage Security Page"..
4. Within the security page - 2 factor authentication section click Manage your application specific passwords. Create an application specific password for your freenas box.. Copy it to the clipboard.. **Note: it will only be displayed once ** An email will be sent to your gmail account as a reminder you created this password..
5. Within the Settings>>Email Tab set the appropriate options to utilize gmail.. (See Image Attachment)
6. With Account>>Users>>>View Users>>"Root"- Set an email as indicated in attachment images..
7. Add email to SMART (S.M.A.R.T) settings... (Hint: Add 40 to critical field in SMART setup)
8. Wait for daily freenas email @ 3am local time daily..
Poll included for usage input..
TY Sir! I enabled 2-step and lost my email notifications. This worked perfectly!