The team here runs jobs on their PC, then has it launch an email, make an attachment, then send it. They can schedule this job. The problem they have is it pops a window asking if you want to send the email being sent by another program, so it snags the idea of overnight jobs that send emails.
What's the prospect of writing a console listener that sits in the tray and watches for this specific window, then simulates the user clicking the send button to dismiss it and send the email?