Your intuitless proposal doesn't answer the question at all.  I don't think you even bothered to read it.  This seems to be par for the course with intuitless customer support.

The issue is that your crappy software doesn't save the password.  I have to re-enter the password every time I email an invoice.

Escalate to someone that has intuition, possibly a supervisor, but even then it's a crap shoot.  Send this to your dev team so they can fix the crumby software!