Backups - which email?

It seems like the mail here is the correct one. If trying to backup through /admin/backups and you have self host, is it supposed to work?

Sidekiq/retries shows many posts with the following:

Jobs::HandledExceptionWrapper: Wrapped Net::OpenTimeout: execution expired

It also shows this one:

Jobs::HandledExceptionWrapper: Wrapped Net::SMTPAuthenticationError: 535 Incorrect authentication data