The company I work for provides testing services for the healthcare industry. As part of our services, we need to send email to our clients' employees. Typically, these are temp, part-time, or contract employees, and so have private email addresses (eg Hotmail, GMail, Yahoo!, etc).

Up to now, we've been sending from an internal address, but this means that replies come back to us when employees aren't paying attention or don't know to send queries to our clients. I'd like to change this, so that the person who requests that the email is sent is the person that is replied to.

We've used reply-to: in the past, but it seemed to cause additional mail to be trapped by spam filters.

I've been reading about sender: and on-behalf-of: headers, and was wondering what the current best-practice was for sending email in a scenario where we need to send email such that the reply goes to a domain we don't control.