I see. Maybe that's because mailtrain adds unsubscribe headers in the email header etc. I don't really know of any other bulk mailer software. Are you able to contact the support of turbo mailer and ask them if they support STARTLS at all?
Are you hosting a custom domain on mailbox.org or do you have a @mailbox.org address? If it's the latter, mailbox is then not really an email relay. Generally, email relays are able to forward all addresses of a domain i.e email@example.com.