For 4 or so years, and with great success, I’ve been using Cobian Backup (For Windows, it’s free BTW) to backup various family PCs, but I had a few problems getting the email notifications to play with a gmail account.

I was aware that I had to use SSL/TLS and port 465, but it still did not work, the fix was to change  a few settings.

Tools|Options|Mail|SSL button, then General tab, for:

• Transport Level Security: select Implicit

• SSL Method: select TLSv1

• Authentication: Auto

• Data port protection: Clear

• SSL mode: Unassigned

• Verify depth: 0

I left all the check boxes clear, and then email notifications worked fine